Toronto Maple Leafs: Ranking All 32 NHL General Managers

With the NHL about to expand to 32 teams, we will see where the Toronto Maple Leafs and Kyle Dubas fit by ranking every general manager in the league.

The Toronto Maple Leafs have made a number of moves with Kyle Dubas at the helm. Some of those have worked out very well while others are less desirable. The same can be said for all general managers in the league but it’s their goal to have more more positives than negatives and ultimately win the Stanley Cup.

While we have ranked the best general managers in Maple Leafs history, this isn’t that sort of list. This is a ranking of every GM in the NHL based on all the moves they’ve made for their club up until this publication in the summer of 2021.

Ranking is always subjective but in order to try and make this as scientific as possible, we will identify both the positive and negative decisions each general manager has made with their current team. We will evaluate their franchise’s successes and failures, giving more weight to the more recent transactions. Using this as a quasi algorithm helped establish the rankings of all the NHL GMs at the conclusion of the 2020-21 season.

32nd Ranked GM – Chris Drury (New York Rangers)

The New York Rangers promoted their Associate General Manager in May, making Chris Drury the new President of the team and their General Manager. It’s a bold move for the franchise who saw Drury play four season for the team as recently as 2011.

It’s very early in Drury’s tenure. So much so that he’s only made two signings so far. He inked his restricted free agent Ryan Lindgren to a three year $9M contract. Drury also locked up Nils Lundkvist to a standard three year $5.325M entry level deal. (All miscellaneous info from nhl.com , stats hockeyreference.com. all cap info capfriendly.com).

Drury is the NHL’s newest GM so he comes in last by default.

31st Ranked GM – Ron Francis (Seattle Kraken)

Ranking Ron Francis is a difficult thing to do. He has yet to make his mark with the NHL’s newest club, the Seattle Kraken, so he can only be judged by his time as the general manager with the Carolina Hurricanes. While there, he made some good hockey moves but a very questionable humanitarian one.

The Good – Francis pulled the trigger on sending a pair of picks, a 2016 second-round pick and a 2017 third-round pick, to the Chicago Blackhawks for two NHL players. The Canes received Teuvo Teravainen and Bryan Bickell (who was included to give the Hawks some cap relief). While Bickell only lasted 11 games with Carolina, Teravainen’s career took off.

Francis also made the wise choice of drafting Sebastian Aho in the second round of the 2015 NHL Entry Draft. In his five years in Carolina Aho has played 366 games where he’s notched 145 goals and 175 assists for a total of 320 points.

The Bad – Francis made a terrible calculation when he signed, then restricted free agent forward, Victor Rask, in July of 2016. Francis gave him a six-year contract worth $24M, which carried an annual cap hit of $4M.

The Ugly – Francis made a decision that many others wouldn’t. After investigations found that his head coach, Bill Peters, had abused players, Francis didn’t fire him. Instead, the coach who was also accused of using racial slurs was given a contract extension by Francis.

In a statement that was released by Francis on his handling of Peters he said, “When I was general manager in Carolina, after a game, a group of players and hockey staff members made me aware of the physical incidents involving two players and Bill Peters. I took this matter very seriously. I took immediate action to address the matter and briefed ownership. To my knowledge, no further such incidents occurred.”

30th Ranked GM – Jim Benning (Vancouver Canucks)

The patience that Francesco Aquilini and Canucks Sports & Entertainment have is quite admirable. They hired Jim Benning in May of 2014, plucking him from the Boston Bruins where he was working as their Assistant GM. Since then, the best single word description for the Canucks would have to be “disappointing”.

The Good – Benning’s best moves have to be his draft record. He’s made a lot of good decisions that have kept the franchise flush with exciting young players. In just his first year on the job, he selected  Jake Virtanen and Jared McCann in the first-round of the 2014 NHL Entry Draft and Thatcher Demko in the second-round.

Benning has also picked up Brock Boeser (first-round 2015), Adam Gaudette (fifth-round 2015), Elias Pettersson (first-round 2017), Quinn Hughes (first-round 2018), and Nils Hoglander (second-round 2019). He gets the credit for those draft selections despite Amateur Scouting Director Judd Brackett believed to be the driving force behind all the above picks.

The Bad – Benning has had a lot of trouble with salary cap management. He’s paid players far more than their value. It’s a mistake that happens with most general managers but Benning has made a habit of it.

Benning signed Tyler Myers to a 5-year, $30M contract. So far, in his two seasons with the Canucks Myers hasn’t registered more than 21 points. Benning also gave Loui Eriksson a 6-year, $36M contract. The 36 year old Eriksson still has a year remaining on that contract after only being able to play seven games this season.

The Ugly – Benning’s inability to retain the important members of his organization may ultimately be his undoing. He famously traded Tim Schaller, Tyler Madden, and a 2020 second-round pick to bring Tyler Toffoli to Vancouver. Benning then failed to re-sign Toffoli at season’s end despite the center expressing publicly that his priority was to remain in Vancouver.

Benning appears to have allowed another key member of the Canucks join another franchise. He let go of Brackett who was very quickly snapped up by the Minnesota Wild to be their Director of Amateur Scouting.

28th Ranked GM – Bob Murray (Anaheim Ducks)

Bob Murray has done a little of everything for the Anaheim Ducks. After working his way up through the Blackhawks organization, Murray joined the Mighty Ducks and eventually replaced Brian Burke as the frachise’s general manager. It’s a role he’s held since November of 2008.

The Good – There was a time when Murray was considered one of if not the best GM in the NHL. He won the Jim Gregory General Manager of the Year Award in for his work in the 2013-14 season. Immediately after earning the award, he Traded for Ryan Kesler in June of 2014. It may have been Murray’s greatest hit. Along with a third round pick, the Ducks managed to acquire the beloved player from who spent ten years in Vancouver for a return of Nick Bonino and Luca Sbisa as well a pair of draft picks. Those were a first-round pick in 2014 which was used to select Jared McCann and a third-round pick in the same draft, which was later traded to New York Rangers. They used it to get Keegan Iverson.

To be clear, trading for Kesler was a good move; the massive contract Murray signed him to a year later, wasn’t. Kesler lasted five years in Anaheim before hanging up his skates. His first three years were fantastic. In fact, Kesler even finished 20th in Hart Trophy voting in 2015-16. The very next year Kesler was even better. He finished the season having played all 82 games and averaging 21 minutes and 18 seconds per contest. He also accumulated 58 points on 22 goals and 36 assists.

Murray also fleeced the Maple Leafs in 2011. He traded the 22nd overall selection to Toronto for the 30th and 39th overall picks. Toronto used their first round choice to take Tyler Biggs. It was a massive bust for the Leafs since he was only one of two players from that round never to play in the NHL. Meanwhile, Murray and the Ducks took Rickard Rakell, who has now been with the organization for nine seasons and John Gibson who has so far played eight seasons between the pipes in Anaheim.

The Bad – Murray has made a number of puzzling deals during his tenure with the Ducks. One of those has to be his second trade of 2015 involving defenseman James Wisniewski. On March 2, Murray acquired Wisniewski and a third-round pick in the 2015 draft (used to selected Brent Gates who never played a game in the NHL) in exchange for Rene Bourque, William Karlsson, and a second round draft pick in 2015, which Columbus used to pick up Kevin Stenlund.

Every single one of the players and picks Murray gave up became individually more valuable than Wisniewski who played just 13 games for the Ducks before he was traded again on June 27. He was sent out of town for Anton Khudobin and his bloated contract. The goaltender started just seven total games for the Ducks and won three of them.

Currently, it looks as though the team has little direction. It finished with the second-worst record in the NHL this season but based on Murray’s decision making, they don’t seem like they are as deep into a rebuild as they should be. However, it should help the organization that they hold the third-overall draft pick in this year’s draft. Murray is surely banking on the prospects he’s drafted developing into impact players. They include forward Trevor Zegras (9th overall pick in 2019), defenseman Jamie Drysdale (6th overall pick in 2020), forward Isac Lundestrom (23rd overall pick in 2018), and forward Jacob Perreault (27th overall in 2020)

The Ugly – In order for Murray to protect all the players he wanted, he swung a deal prior to the Vegas Golden Knights Expansion Draft. The Ducks sent then 21-year-old defenseman Shea Theodore to protect the rest of his roster. It was an odd move since Theodore is precisely the type of player that a team would have protected if needed. Making it an even worse decision was the fact that Murray traded away Sami Vatanen only four months later. It was a move that if done sooner could have saved Anaheim from losing their young up-and-coming defenseman.

27th Ranked GM – Kevyn Adams (Buffalo Sabres)

After spending nearly nine months as the Buffalo Sabres Executive Vice-President, Kevyn Adams was promoted to be the team’s general manager. Getting the job in June, he’s now had the role for a year, long enough to make his mark with the club.

The Good – One of the most critical decisions Adams made was identifying that his head coach, Ralph Krueger, was not the right man to have behind the bench. Krueger was in his second season behind the bench with Buffalo where he lasted just 28 games before Adams removed him from the position. Krueger had 6 wins and 18 losses when Adams replaced him with an interim head coach, Don Granato. Last month, Granato shed the interim title and will return next season.

The Ugly – In what was an otherwise bleak season for the Sabres, they had a standout campaign by their goaltender, Linus Ullmark. Before the start of the season, the Swede signed a one-year $2.6M contract to play in Buffalo. Adams mistake was to allow Ullmark to reach free agency without getting anything for him. Now an unrestricted free agent, he will be a valuable player for an organization looking for a stopper. Ideally, Adams would have either signed Ullmark to a contract extension or traded him at the deadline when it was clear that the club wasn’t going to make the playoffs.

The Ugly – In Adams’ short time as the Sabres GM, he signed former first overall draft pick Taylor Hall to a one-year $8M contract. Hall failed to perform to the level of his cap hit. He scored just two goals in the 37 games he played in Buffalo.

Knowing that Hall would walk as an unrestricted free agent at season’s end, Adams traded Hall to Boston for a meager return. Hall was traded along with Curtis Lazar for only Anders Bjork and a 2021 second-round pick. Adams also retained half of Hall’s salary.

If the Toronto Maple Leafs hadn’t just traded away a first and fourth-round draft pick for Nick Foligno and the Lightning hadn’t coughed up a first and a third-round pick for David Savard, perhaps the haul Adams managed to acquire would feel suitable. Instead, it falls short of a fair return for Hall.

26th Ranked GM – Tom Fitzgerald (New Jersey Devils)

Similar to Adams, the New Jersey Devils have only recently hired their general manager, Tom Fitzgerald. Just like Adams, Fitzgerald is inheriting a mess. Some of that should fall on Fitzgerald’s shoulders since he was around to help set the table before taking the GM job. Fitzgerald has been with the Devils since 2015 working as the team’s Assistant GM. He became the team’s Interim GM in January of 2020 and had the “interim” title removed six months later.

The Good – Recognizing the need for the Devils to make some moves to improve the team for the future, Fitzgerald went into last season’s trade deadline with a mission. It was one he accomplished. He traded Blake Coleman to the Tampa Bay Lightning for Nolan Foote and a first round draft pick in last year’s draft. Fitzgerald used that pick to select Russian defenseman Shakir Mukhamadullin.

That same trade deadline, Fitzgerald made another strong move. He dealt Andy Greene to the New York Islanders for David Quenneville and a second-round pick in the 2021 draft. While we have yet to see what Quenneville can bring to the Devils, gambling on him and the prospect Fitzgerald selects with the pick was well worth the trade.

The Bad – While Fitzgerald’s predecessor, Ray Shero, was running the Devils, he had Fitzgerald in his corner for the entire ride. Shero’s is the one who is responsible for the moves made during his tenure but Fitzgerald’s hands aren’t clean from that era. He was a part of the group that traded away a pair of draft picks for Mirco Mueller. Mueller remained with the organization until Fitzgerald was finally able to let him walk in free agency.

The Ugly – Fitzgerald traded for Ryan Murray to be one of their top defensemen this past season. Not only was Murray overpaid, earning $4.6M, but he was also more of a liability for the Devils than he was helpful. The blueline was so bad this year that despite Murray’s underwhelming play, he still was tasked with consuming an average of 18 minutes and 37 seconds of ice time per game.

25th Ranked GM – Bill Armstrong (Arizona Coyotes)

Admittedly, Bill Armstrong has not been at the helm of the Arizona Coyotes very long. He was only hired in September 2020. Before then he worked as an assistant GM for the St. Louis Blues. His success in St. Louis earned him his current position in the desert.

The Good – Though he’s only been on the job a short time, Armstrong has signed 17 player contracts worth $26,690,000. He also managed to make an excellent deal for the franchise, getting out of Derek Stepan’s expiring $6.5M contract. Armstrong shipped Stepan to the Senators and managed to get a second round pick for him.

The Bad – Armstrong appears to be playing things safe in his nearly ten months as Arizona’s GM. For a team stuck in the bottom-middle of the league, they need action that will help them rebuild their roster into a winner. That usually involves some risk. Perhaps, Armstrong is biding his time and waiting for just the right moment to make a splash.

The Ugly – It didn’t happen under Armstrong’s watch but the Coyotes were forced to forfeit their 2020 second-round and 2021 first-round draft picks because they violated the NHL’s Combine Testing Policy. However, Armstrong took the job with Coyotes knowing that the team is in a very difficult position with an ownership team that will likely never spend to the cap. Armstrong started in the red and needs to now prove that he has what it takes to turn the franchise around. Hopefully, the Coyotes are patient with their new GM.

The 24th Ranked GM – Ron Hextall (Pittsburgh Penguins)

In January this season, the Pittsburgh Penguins decided they needed to make a change. After six years under Jim Rutherford, ownership wanted a new general manager. Enter Ron Hextall who took the job in February. It is now his second stint as an NHL GM after spending four and a half years in the role with the Philadelphia Flyers.

The Good – There isn’t much to judge Hextall on since he’s only been the Penguins GM for five months. As such, we can only base his body of work on what was done in Philadelphia. In 2015, Hextall had an important decision to make at the draft. Picking seventh overall, the fifth-ranked prospect by NHL Central Scouting, Lawson Crouse, was still on the board. Instead, Hextall decided to take Ivan Provorov. Looking back, it was a great decision.

It gets better for Hextall in that draft. He wisely traded up thanks to the help of the Toronto Maple Leafs. They moved their first round pick at slot number 24 for Hextall’s 29th and 61st overall picks. The Flyers ended up with Travis Konecny and the Leafs got Gabriel Carlsson and Jeremy Bracco.

The Bad – As a former goalie himself, it’s strange that making decisions on them appears to be Hextall’s weakness. He swung a deal in 2018 for Petr Mrazek. It only cost Hextall a third-round pick but Mrazek was a downgrade in net, which really made no sense at the time.

The Ugly – Once again, goaltenders are Hextall’s undoing. In 2017, a year prior to making a mistake on Mrazek, Hextall made a pair of errors. That’s because in the span of four months he handed out two lucrative contracts to stoppers. Hextall gave Michal Neuvirth a two-year extension worth $5M. It carries a $2.5-million AAV. After completing those two seasons, Neuvirth called it a career. He wasn’t great in either season but he must have been happy. Afterall, Hextall helped him cash in.

The other played Hextall signed was Brian Elliott. Elliott also signed for two years but for slightly more money. Hextall handed him a $2.75-million AAV. He too wasn’t impressive but at least Elliott has remained with the franchise since inking that deal.

The 23rd Ranked GM – Jarmo Kekalainen (Columbus Blue Jackets)

The Columbus Blue Jackets are an exciting team to watch off the ice thanks to their longtime general manager Jarmo Kekalainen. He has been in the position for nearly eight and a half years. In that time, he has made a lot of decisions that have both helped and hurt the organization.

The Good – Kekalainen’s best moves both include Brandon Saad. The GM made a massive seven-player deal in June of 2015 with the Blackhawks. Kekalainen acquired Saad along with with Alex Broadhurst and Michael Paliotta in exchange for Artem Anisimov, Marko Dano, Jeremy Morin, Corey Tropp, and a fourth-round draft pick in 2016, which was later traded to the Islanders who used the pick to select Anatoli Golyshev. Saad instantly became successful in Columbus and even made the All-Star team.

Kekalainen made a great decision after seeing Saad thrive. After just two seasons together, the general manager flipped the winger back to Chicago in a package to get a point producing machine, Artemi Panarin.

The Bad – In 2014, Kekalainen was on the losing end of a trade. He sent Marian Gaborik to the Los Angeles Kings for Matt Frattin and an pair of draft picks. In Gaborik’s first year with the Kings, he exploded for 27 goals and 20 assists, looking more like the player he was when he played for the New York Rangers.

The Ugly – The deal that Kekalainen made this January to acquire Patrik Laine and Jack Roslovic in exchange for Pierre-Luc Dubois and a 2022 third-round draft pick, first looked like it was a steal for Columbus. It got ugly when Kekalainen allowed his coach, John Tortorella, to bench and repeatedly punish the team’s new sniper.

Totorella is polarizing figure in hockey but his coaching style has a shelf life. It appears as though it has expired in with the Blue Jackets, yet Kekalainen hasn’t yet removed Torts from the role. This season, he led the team to a record of 18-26 while continuing to make negative headlines for his coaching decisions.

The 22nd Ranked GM – David Poile (Nashville Predators)

If Wilson’s 18 year run is impressive, prepare to be blown away. David Poile has been the GM of the Nashville Predators since its inception in 1997. Having worked in the NHL since the 1970s, Poile previously worked as the general manager of the Washington Capitals before he took the reins of the Predators 24 years ago.

The Good – Poile had an excellent season with the Preds in 2016-17. That year, his team advanced all the way to the Stanley Cup Finals for its only appearance there. Thanks to moves such as trading Shea Weber to the Montreal Canadiens for P.K. Subban and signing Yannick Weber and Matt Carle, the team excelled. It also helped that Viktor Arvidsson had an outstanding season.

The Preds ended up losing the finals to the Pittsburgh Penguins but Poile was rewarded for his team’s success. That year, he won his one and only Jim Gregory General Manager of the Year Award.

The Bad – A part of the general manager’s job is to protect their valuable assets. That can be difficult with expansion drafts. Poile failed to protect James Neal and didn’t make any trades ahead of time to ensure that Vegas wouldn’t claim the crafty winger. The Golden Knights took advantage of Poile’s error and snatched Neal and his strong play.

The Ugly – P.K. Subban has been a fan favourite everywhere he’s played. That’s why fans were upset when Poile dealt the blue liner to the Devils for a pair of second-round picks and a couple of prospects, Jeremy Davies and Steven Santini. The move was made in order to clear space for Poile to sign Matt Duchene to a massive contract.

Trading away Subban wasn’t great but the contract the Predators gave Duchene is ugly. They signed him for seven years and $56M. That’s an AAV of $8M. The contract also carries a no-trade clause in its final three seasons. This season, Duchene registered 13 points in 64 games. He still has five years left on the contract.

The 21st Ranked GM – Brad Treliving (Calgary Flames)

The Calgary Flames have trusted their current GM, Brad Treliving, to do the job for the past seven years. He is just their eighth general manager in franchise history. In that time, Treliving’s Flames have won nearly an equal amount of games that they’ve lost. This past season, Treliving was certainly disappointed that his group didn’t qualify for the postseason.

The Good – Treliving has always been good at finding the right players in the draft. There is no better example than who the Flames plucked out of the third round of the 2016 NHL Entry Draft. With the 66th overall pick, they took this year’s Norris Trophy winner, Adam Fox.

The Bad – After drafting for Fox’s rights, the team could only watch the defenseman play for Harvard University because he refused to sign with Calgary. Treliving decided to trade Fox Instead of losing him for nothing. It’s hard to hold this against Treliving but he did have a stud defenseman that he was unable to get into a Flames uniform.

If you’re willing to give Treliving a pass on Fox, we can point to some of his head scratching signings. Chief among them would be the four-year contract that he gave to winger Troy Brouwer in 2016. Brouwer was given $18M with a $4.5M AAV. Treliving wasn’t able to move that contract so he was forced to buy out Brouwer. How much was he worth? Well, following the buy out Brouwer signed with the Florida Panthers for $850,000.

The Ugly – Treliving really wanted to acquire Travis Hamonic and he was willing to mortgage the future for D-man. The Flames sent the Islanders a first and a second-round pick in the 2018 draft. They also gave them a second-round draft pick in 2019.

As ugly as that looks, it could have been worse if the Islanders had made better selections. They used the 2018 picks to get defenseman Noah Dobson and center Ruslan Iskhakov. In 2019, they drafted defenseman Samuel Bolduc.

The 20th Ranked GM – Rob Blake (Los Angeles Kings)

Rob Blake was a hockey hero in LA thanks to his 14 years of playing for the city. After he hung up his skates, Blake made his way back to the Los Angeles Kings and took a job in the front office as their Vice President of Hockey Operations and Assistant General Manager. In April of 2017, he gave up those titles to be the Kings’ GM.

The Good – Blake has managed to stock his organization’s farm system thanks to some solid draft pickups. Holding the eight pick in this year’s draft, that’s also sure to improve. Last year, the Kings selected the mega talented center from the Sudbury Wolves Quinton Byfield. He may be ready to play in the NHL as early as next season.

It will be interesting to watch the Kings’ prospects come up together. Blake has also drafted players such as Alex Turcotte in 2019, Tobias Bjornfot in 2019, Rasmus Kupari in 2018, and Gabriel Vilardi in 2017. If these players all hit their stride together it should mean huge success for the Kings.

The Bad – The reason that Blake has managed to accumulate so many young and talented prospects via the draft is because his teams have not been very good. While a rebuild does take time, Blake is certainly testing the Kings fanbase’s patience. In Blake’s four years on the job, the franchise has only made the playoffs once. That year, they were bounced out of the first round by Vegas.

The Ugly –  For such a pretty player, ugly seems to follow Ilya Kovalchuk. This was certainly the case for his time with the Kings. While Blake looked like a hero on July 1, 2018 signing both Drew Doughty and Kovalchuk to massive deals, only one of them lasted.

Kovalchuk signed for three years at $6.25M per season. He lasted just one and half before Blake released him. The cap hit however stuck around all three years. Kovalchuk was benched for 18 consecutive games before he basically quit on the team. He also managed to earn $14M from the Kings for playing just half his contract. This wasn’t a good look for either Los Angeles or Blake.

The 19th Ranked GM – Chuck Fletcher (Philadelphia Flyers)

Chuck Fletcher has been an executive in the NHL since 1993 and has held some type of management position for seven different NHL organizations. He became the Philadelphia Flyers GM in December of 2018. Fletcher is the son of the current Senior Advisor to the Maple Leafs, The Silver Fox Cliff Fletcher.

The Good – Chuck Fletcher clearly understands the value of a strong blue line. He has ensured that this is the backbone of his teams. Fletcher has done an excellent job in signing his defensemen. He inked Travis Sanheim to a two-year bridge deal with an AAV of $3.25M. Ivan Provorov was signed for six years with a cap hit of $6.75M, Phil Myers for three years with a $2.55M AAV, and Justin Braun for two years with a $1.8M cap hit.

The Bad – As much as Fletcher deserves credit for securing a solid defensive core, he should be questioned for backing the Brinx Truck into Kevin Hayes‘ driveway. Fletcher gave the team’s second line center $50M over seven years. That’s an AAV of $7,142,857. This season, Hayes recorded 31 points on 12 goals and 19 helpers in 55 contests.

The Ugly – The 2019 NHL Entry Draft was headlined by Jack Hughes being the first-overall pick. The Flyers had the 14th overall selection and Fletcher decided to use it on American defenseman Cameron York. It’s too early to tell whether this was a horrendous decision as there is still great hope that York can be one of the team’s cornerstone players. However, in order to draft York, they needed to pass on the best pure scorer in the draft, Cole Caufield. The Montreal Canadiens scooped up Caufield with the very next pick, much to their delight.

The 18th Ranked GM – Kevin Cheveldayoff (Winnipeg Jets)

In June, Kevin Cheveldayoff celebrated being the Winnipeg Jets’ Executive Vice-President and General Manager for ten years. It was a run that started with the Thrashers. It’s been a roller coaster ride for Cheveldayoff and the team who have made it as far as the Western Conference Finals in 2018.

The Good – Without question, the best move Chevaldayoff made was in 2014 when he released Claude Noel mid-season and replaced him with Paul Maurice. The coaching change set up the team for six and half seasons and Maurice remains the bench boss today.

From a drafting and signing perspective, Chevaldayoff can be given the nod for selecting Mark Scheifele seventh overall in 2011. He has gone on to be the Jets best player, which is why their GM deserves credit for also locking up the center with an eight year contract in July of 2016 worth $49M. It carries an AAV of just $6.125M.

The Bad – In the summer of 2012, Chevaldayoff manage to win the Olli Jokinen sweepstakes. He paid a big price for the Finish center. Jokinen was given a two year $9M contract. It carried both a $4.5M cap hit and a no-trade clause. In his first season Jokinen posted putrid numbers. In 45 games, he scored seven goals and had seven assists. Jokinen bounced back in the second year of the deal as he became known to be a lame duck stud.

The Ugly – Jokinen wasn’t Chevaldayoff’s worst signing. That might be reserved for current Maple Leafs defenseman, Zach Bogosian. The Jets loved what Bogosian brought to the table so they locked him up long term in 2013. Chevaldayoff extended the blue liner for seven-years in a deal worth $36M.

Things didn’t work out for Bogosian and the Jets. Chevaldayoff must have recognized the ugly situation for what it was and decided to cut bait in 2015 when he included Bogosian as part of a package with Evander Kane and Jason Kasdorf and shipped them to the Sabres. In return, Chevaldayoff received Joel Armia, Brendan Lemieux, Tyler Myers, Drew Stafford, and a first round draft pick which was used to draft Jack Roslovic. Not a single one of those players is with the organization today.

The 17th Ranked GM – Bill Guerin (Minnesota Wild)

The Minnesota Wild made a wise move to hire Bill Guerin as their franchise’s fourth general manager. Guerin has won a pair of Stanley Cups as the Assistant General Manager of the Penguins. He also won two of them as a player, one with New Jersey and the other with Pittsburgh. Minnesota is Guerin’s first chance to prove that he’s ready to be an NHL GM. So far, he’s been in the role since August of 2019.

The Good – Guerin has been busy trying to elevate his team into a title contender. One deal he made that significantly helps the franchise is dumping one of his predecessor’s bad contracts. Guerin swung a deal that sent Jason Zucker to the Penguins, relieving the Wild of his $5.5M cap hit that would have been on the books until the completion of the 2022-23 season.

This wasn’t just a good trade, it was great. In exchange for Zucker, Guerin received a 2021 first-round draft pick, WHL prospect Calen Addison, and Toronto Maple Leafs reclamation success, Alex Galchenyuk. Pittsburgh wanted out from Galchenyuk’s contract but since it expired at the end of the 2019-20 season, it made a lot of sense for Guerin to take him.

Guerin needs to also be commended for managing to lock up his team’s captain, defenseman Jared Spurgeon. In September of 2019, he was signed to a massive seven year contract worth $53.025M. Spurgeon will be under team control until at least the end of the 2026-27 season.

The Bad – In an attempt for the Wild to bolster their roster and pick up draft picks, Guerin swapped centers with the Predators. Going to Minnesota was Nick Bonino who would be there as a one year rental to hopefully help the team once they made it into the playoffs.

While Bonino did have a solid regular season, he disappeared in the playoffs, registering no points in the Wild’s seven game series against the Golden Knights. In exchange for Bonino, the Preds managed to pry away center, Luke Kunin. The 23 year old looked great playing in just his fourth NHL season. Kunin went to Nashville along with a fourth round pick in last year’s draft, which the team used to select 2020 4th Adam Wilsby.

Even though Bonino didn’t play up to expectations and can potentially walk as an unrestricted free agent this summer, this was a bad trade for Guerin but not a terrible one. He also managed to wrangle a pair of picks in the 2020 draft out of Nashville. Minnesota received a second-round pick, which they used to take Marat Khusnutdinov and a third-round pick, with which they selected  Eemil Viro.

The 16th Ranked GM – Doug Wilson (San Jose Sharks)

It’s almost unfathomable to think that Doug Wilson has been the general manager of the Sharks since May of 2013. He has been in the role for over 18 years. That means he could be drafting players this year who weren’t even born when the Sharks first hired Wilson to be their GM.

The Good – Wilson has managed to find some valuable players very deep in the draft. He took Nick Bonino (2007) Tommy Wingels (2008), and Dylan DeMelo all in the sixth-round. He did even better with a pair of seventh-round selections. In 2003, Wilson drafted Joe Pavelski 205th overall. He did it again in 2008 when the Sharks selected Jason Demers 186th overall.

The Bad – While Wilson can be lauded for his success finding NHL regulars at the back of the draft, he can be equally criticized for some moves he made in the first round. Some of his worst were after trading up to get better picks.

In 2005, Wilson traded it’s 12th overall pick to the Atlanta Thrashers, which they used to select Marc Staal, their second-round pick, used on Chad Denny, and their seventh round pick, which turned into Myles Stoesz. Wilson moved the trio of picks to move up to seventh overall where he drafted Devin Setoguchi.

That was actually the second time Wilson traded up in a draft. The first was in 2003. In a cohort loaded with talent, Wilson wasn’t happy picking with the 21st selection. He managed to get himself up to 16. In that slot, Wilson and the Sharks chose Steve Bernier. While he played well in San Jose, one must wonder what could have been if he had chosen one of the players that was drafted after Bernier in the round. They include Zach Parise, Ryan Getzlaf, Brent Burns, Mark Stuart, Ryan Kesler, Mike Richards, Brian Boyle, Corey Perry, and Patrick Eaves.

The Ugly – It’s hard to look at Erik Karlsson’s current contract and not feel bad for the Sharks. Wilson locked the blueliner up for eight years in 2019. He signed the unrestricted free agent to a contract worth $92M, which carries an AAV of $11.5M. Now 31 years old, Karlsson still has six years remaining on his deal.

The 15th Ranked GM – Don Waddell (Carolina Hurricanes)

Don Waddell has been the general manager for the Carolina Hurricanes since March of 2018. He transitioned into the role after spending seven years as the organization’s President. Waddell had a lot of experience before joining Carolina because he had the chance to work for the Detroit Red Wings as their Assistant General Manager and held various roles with the Atlanta Thrashers. Those included being their President, Head Coach, and GM of the franchise. While there is a lot that can be drawn on from Waddell’s time with the Thrashers we will only focus on his work with the Canes.

The Good – Waddell’s first offseason was excellent. He managed to acquire a bunch of new players, which included Dougie Hamilton, Micheal Ferland, Petr Mrazek, Calvin De Haan, and Jordan Martinook. Thanks to his smart decision making, he was named a finalist for the GM of the Year Award in 2019. Ultimately, Don Sweeney with the Bruins captured the prize.

The Bad – Carolina was in a tough spot with Hamilton this past season. He was clearly a very valuable member of the roster but he was also a pending unrestricted free-agent. One of Waddell’s most important moves during the season would have been to extend Hamilton’s contract. Instead, it was reported that both parties were far apart in their negotiations before they finally broke off. It now looks like the Hurricanes could lose the defenseman this summer with no return.

The Ugly – It’s only a coincidence that Hamilton is linked to all of Waddell’s good, bad, and ugly decisions. A part of the deal that brought Hamilton to the Canes and sent Noah Hanifin to the Flames was the inclusion of Aaron Fox.

As previously detailed, it looked as though Fox wasn’t going to sign with Calgary so they used him to help sweeten the pot in a five-player deal. Unfortunately for Waddell and the Hurricanes, they too couldn’t get Fox to agree to play for their organization. Waddell ended up trading Fox ten month later to the Rangers for a pair of draft picks, nowhere near the worth of the 2021 Norris Trophy Winner.

Those draft picks were used to select Mads Sogaard in 2019 and Noel Gunler in 2020. It’s too early to tell whether those players will develop into valuable pieces for the Canes but it’s very unlikely they’ll ever be on Fox’s level.

The 14th Ranked GM – Kyle Dubas (Toronto Maple Leafs)

In May of 2018, Kyle Dubas became the 17th GM of the Maple Leafs. At that time, he was the second youngest person to have the role in the NHL. Dubas was just 32 years old. The youngest was John Chayka of the Coyotes who was just a month away from his 29th birthday.

Dubas took over for Lou Lamoriello, beating out his co-assistant GM Mark Hunter. Helping Dubas elevate himself above Hunter to earn the GM job in Toronto was both his work with the Calder Cup winning Toronto Marlies as well as his forte in using data and analytics.

The Good – There is a lot to like about the way Dubas has managed in Toronto. He has done extraordinarily well at signing free agents. His biggest UFA acquisition would have to John Tavares, who would later be named the team captain. Dubas has a number of excellent signings including hockey hero Jason Spezza, Wayne Simmonds, T.J. Brodie, and Joe Thornton.

Dubas has also shown that he can be quite crafty. For example, one of the first trades Dubas ever made as GM was in the 2018 NHL Entry Draft. He sent pick number 25 to the Blues in exchange for pick 29 and 76. St. Louis used their selection to take Dominik Bokk who has yet to reach the NHL. Meanwhile, Dubas and the Leafs used their new slots to draft Rasmus Sandin and Semyon Der-Arguchintsev.

The Bad – What keeps Dubas stuck in the middle of the pack of NHL general managers is his team’s inability to win playoff rounds. Their lack of success has crushed Leafs fans for years. In all his different roles with the organization, Dubas hasn’t able to help the Leafs win a single playoff series.

The Ugly – There is no uglier stain on Dubas’s tenure than his contract negotiations with both William Nylander and Mitch Marner, both of whom were restricted free agents at the time.

Nylander’s camp and Dubas went back and forth for a long time but weren’t able to come to a decision prior to the start of the season. Their negotiations actually lasted two months into the season and were finally settled on Dec. 1, 2018, mere minutes ahead of the NHL deadline to sign RFAs.

The Marner negotiations weren’t quite as dramatic and their dispute didn’t last nearly as long. The two sides came to an agreement at the start of training camp on Sep. 13, 2019. Many speculated at the time that Dubas was gun shy after his experience with Nylander, which is why he gave Marner such a massive contract. The winger was signed to a six-year $65.408M deal, which carries an AAV of $10.903M.

The 13th Ranked GM – Jim Nill (Dallas Stars)

For over eight years Jim Nill has been the GM of the Dallas Stars. He cut his teeth working in the Red Wings front office starting all the way back in 1994 at the age of 35. He transitioned seamlessly from Detroit to take his current role in 2013.

The Good – There is always something to like about a GM who can build a team that can realistically win a championship. Last year, Nill’s Stars came just two wins away from hoisting it but ultimately fell in the Finals to the Tampa Bay Lightning.

A big part of the team’s success has to be because of a trade that Nill made in July of 2013. He pulled the trigger on a seven player deal with the Bruins that allowed the Stars to get Tyler Seguin. The big part of the return for Boston was Loui Eriksson but the Bruins also received Matt Fraser, Joe Morrow, and Reilly Smith. Along with Seguin, the Stars got Rich Peverley and Ryan Button. It was an absolute steal for Nill.

The Bad – On the opening day of free agency in 2017, Nill announced that he had signed UFA center Martin Hanzal to a three-year $14.25M. That was an AAV of $4.75M. This was a bad bet by Nill because Hanzal was 30 at the time of the signing and had already had nagging health issues. He had a foot injury and was coming off his second back surgery when Nill inked him to far too large a deal.

The Ugly – Some may wonder what happened to the Stars this season. They went from almost winning Lord Stanley’s Mug to not even qualifying for the playoffs. The problem is that injuries ravaged the team. It was really ugly.

Not only did a number of players miss significant time but the players who did were very important to the team. Goaltender Ben Bishop had to sit out the entire season to rehab a knee injury. After playing just 11 games, Alexander Radulov had to miss the rest of the season to surgically repair a core muscle injury. Seguin was also limited to just a handful of games. He played in only three because he was rehabbing from hip surgery. Clearly, this isn’t Nill’s fault but it did ruin any hope that the Stars had of returning to the Finals.

The 12th Ranked GM – Ken Holland (Edmonton Oilers)

In 1987, Ken Holland took the job of Director of Amateur Scouting with the Red Wings. He built a phenomenal career there, building his way up to become their general manager. Holland even won the Stanley Cup four times in Detroit. When the team moved him into a different position, Holland left to join the Edmonton Oilers. He’s been their GM since May of 2019.

The Good – While he hasn’t had a lot of time in Edmonton, Holland has already made some strong decisions. His first trade was actually a big one. He unloaded Milan Lucic and his $6M cap hit in exchange for James Neal.

Holland recently extended an important player to a very team friendly contract. He signed the former first-overall draft pick, Ryan Nugent-Hopkins, for the next eight seasons. The contract is worth $41M and carries a $5,125M AAV.

The Bad – In January of 2020, Holland overpaid for Zach Kassian. One must wonder what the UFA’s other offers were before he signed in Edmonton for four years and $12.8M. The 30 year old now has three year left on that deal with an average cap hit of $3.2M. After the first year on that contract, Kassian played 27 games and only recorded two goals and three assists.

The Ugly – In 2019, in a move to clear cap space, Holland bought out Andrej Sekera. The move didn’t save the club a fortune, but allowed for more cap flexibility. Buyouts are always ugly but Sekera was snapped up quickly by the Stars. He was an important blueliner for the team in his first year in Dallas, playing an average of 18 minutes per game. That did drop off this past season but Sekera still brought value to his club.

The 11th Ranked GM – Stan Bowman (Chicago Blackhawks)

The GM for the 2022 Beijing Games U.S. Olympic men’s hockey team has a full time job in the NHL. It’s one he’s held for 12 years. Stan Bowman became the general manager of Blackhawks in 2009. Stan is the son of legendary coach and current Senior Advisor for the Hawks, Scotty Bowman.

The Good – There is a lot of good on Bowman’s resume but nothing can beat the three Stanley Cups he’s captured. While there were a lot of moves that were needed in order to make the necessary tweaks to help the club ascend to the peak of the league, it did help that there were stars already on the roster when Bowman joined the Hawks. They included Jonathan Towes, Patrick Kane, Duncan Keith, and Brent Seabrook. Incredibly, Bowman managed to keep all four of those players in Chicago until Seabrook retired due to injury.

Somehow Bowman managed to convince the Oilers to take on the remainder of Keith’s contract this week. He even got compensated for it by receiving a 24 year old defender in Caleb Jones as well as a third round pick in this year’s draft.

The Bad – There have been a lot of transactions made during Bowman’s tenure. Many of them are good but there is no defending the trade he made in October of 2014 to ship out Nick Leddy. Bowman knew what he had with the dynamic defenseman but decided to move him for cap management’s sake.

Bowman traded Leddy along with Kent Simpson (who played only one career games in the NHL) to the Islanders for T.J. Brennan, Anders Nilsson and Ville Pokka. It was a meager return for a stud player. To make things worse, Leddy will be in the final year of the contract he signed with the Islanders. His contract carries a very reasonable $5.5M AAV.

The Ugly – If you’re thinking that the Leddy deal was ugly, well it does get worse. Bowman was behind the trade that sent Artemi Panarin to the Blue Jackets for a fifth round draft pick in 2018, goaltender Anton Forsberg and Brandon Saad.

In Forsberg’s six years in the NHL, he has played in a total of 56 games. He has collected 15 wins in that time. Saad was more useful. He had the best two seasons of his career immediately following the trade to Chicago. He collected 53 points both years. While that’s decent, it’s nothing compared to what the Bread Man was able to do.

Before being moved to Columbus, the lowest point total Panarin had was 74 points. Until this past year, playing in a shortened season, it was still his lowest. In 2020, Panarin finished third in Hart trophy voting when he registered 95 points in just 69 games. It wouldn’t be surprising if Bowman has nightmares about this terrible trade.

The 10th Ranked GM –  Kelly McCrimmon (Vegas Golden Knights)

When the Golden Knights joined the NHL, their general manager was George McPhee. His Assistant GM was Kelly McCrimmon. When McPhee moved out of his role in 2019 to concentrate on being the franchise’s President of Hockey Operations, McCrimmon took over as the GM. He has been in charge for nearly two years.

The Good – McCrimmon has been able to sign big name free agents such as Alex Pietrangelo and Robin Lehner, however, the move that makes him stand out is the trade he made for Chandler Stephenson. Somehow McCrimmon saw something in the center that no one else did. He gave the Capitals a fifth-round pick in the 2021 draft for him. Stephenson developed enough to not just earn himself far more ice time but also a four-year $11M contract.

The Bad – It’s very difficult to find anything overly egregious that McCrimmon has done. The worst that can be said about him is that he isn’t McPhee. McCrimmon’s mentor set up a roster that began near the top of the league and remained there. While McCrimmon has maintained nearly the same level of success, with his club going as far as the Stanley Cup Semi-Finals, McPhee still deserves some of the credit there.

The Ugly – During the playoff series that the Golden Knights played against the Canadiens, McCrimmon was shown on television taking in Game 3 from a suit in the Bell Centre. He and McPhee watched the game without wearing their masks, which was in direct violation of the league’s COVID-19 Protocol.

McCrimmon tested positive for the virus, which means he exposed his 63 year old mentor without taking the simplest of precautions. McCrimmon and McPhee were warned about their actions by the NHL and reminded to follow safety protocols.

The 9th Ranked GM – Brian MacLellan (Washington Capitals)

For the last seven years, Brian MacLellan has been the GM of the Capitals. He spent ten years, starting in 2004, as the Director of Player Personnel. MacLellan then worked his way up to add Assistant GM to his portfolio before he traded both those roles to be the General Manager and Vice President of Hockey Operations.

The Good – While everyone was celebrating Alex Ovechkin winning the Stanley Cup for the first time, they may have forgotten all the work that MacLellan did to elevate his team to that point. Let’s not forget how pivotal T.J. Oshie was for that 2018 Cup run.

Oshie was unstoppable in those playoffs. Playing over 20 minutes a night, he finished with 8 goals and 13 helpers for a total of 21 points in 24 games. MacLellan traded Troy Brouwer and Pheonix Copley as well as a third-round pick in order to secure Oshie.

The Bad – General managers need to sometimes take big risks. That’s what MacLellan may have done this past offseason when he extended Nicklas Backstrom. To be clear, keeping Backstrom in Washington was a great decision. The size of the contract that was given to a player on the wrong side of 30 is almost certain to backfire before it expires.

MacLellan signed Backstrom to a five-year $46M contract. That means the center is playing on a $9.2M AAV. That will be Backstrom’s cap hit when he’s 37 in the final year of the deal. Of course, I could be wrong and Backstrom could continue producing at his current pace but it doesn’t seem likely.

The Ugly – Tom Wilson. Enough said.

The 8th Ranked GM – Don Sweeney (Boston Bruins)

For the last six years, Don Sweeney has been the general manager of the Boston Bruins. He has impressed in the role, even winning the Jim Gregory General Manager of the Year Award for his work in the 2018-19 season. Sweeney was also the Assistant GM for the Bruins when they won the Cup in 2010-11.

The Good – Recognizing that Taylor Hall still had top six potential despite his poor play, Sweeney made a move for the winger at the 2020-21 trade deadline. It’s amazing that Sweeney wasn’t arrested for the transaction because he absolutely stole Hall for the price of Anders Bjork and a 2021 second-round pick. Not only did Sweeney get Hall in that one-sided transaction but he also received 26 year old Curtis Lazar.

The Bad – On opening day of free agency in 2016, Sweeney signed a big free agent who had eclipsed the 20-goal mark in each of his previous three seasons. He negotiated a five-year $30M contract with David Backes which included a no-movement clause for the first three years and a no conditional trade-clause for the final two seasons.

The contract, which paid Backes $6M per season, remains the third-highest AAV Sweeney’s ever given a player. It sits behind just David Pastrnak’s $6,666,667 and Brad Marchand’s $6,125,000 cap hits. Sweeney never came close to living up to his contract. He didn’t managed to score more than 17 goal in a season.

The Ugly – To get rid of Backes and rid the Bruins of the forward eating too much cap space, they managed to find a dance partner and sent him to the Ducks. Getting out of the contract wasn’t so simple, Sweeney had to also send a first-round pick and Axel Andersson. It’s too soon to know if the Bruins gave up a lot in the right-shooting defenseman as he spent this past season splitting time between playing in Sweden and for the Ducks AHL affiliate, the San Diego Gulls.

This trade wouldn’t have looked so bad for Sweeney if perhaps the player that Boston got back played to his potential, but that’s not how things went. Anaheim shipped Ondrej Kase, the Czech right-winger, east. He arrived in Boston already injured and was limited to just six regular season games a year ago. Kase managed to only register one point on an assist. In the playoffs, he picked up four more, playing in 11 games.

This past season, Kase didn’t play in any games and injuries once again held him off the ice. He played just three regular season games and didn’t get his name recorded on any of those score sheets. Kase is now a restricted free agent, which means it’s possible that this ugly situation could either improve or look even worse in the coming days.

The 7th Ranked GM – Steve Yzerman (Red Wings)

There are very few players in the modern era who played their entire career for just one franchise. That’s especially true for someone who lasted 22 years in the NHL. That’s why it was strange to see Steve Yzerman dressed in his suit, working for a team that wasn’t the Red Wings. He spent almost nine years with the Lightning before going home to where he truly belongs, in Detroit. Yzerman joined the Red Wings as their General Manager a little more than two years ago, in April of 2019.

The Good – The vision Yzerman has in the board room may be equal to what he brought on the ice. That helped him build a reputation in Tampa as a cunning GM who appeared to be a step ahead of others. It may be too early to tell but Yzerman will look like a genius if defenseman Moritz Seider becomes the player the Red Wings think he’ll become.

Detroit drafted Seider well ahead of where most had him ranked. Yzerman used the sixth pick of the 2019 NHL Entry Draft on Seider, making him the second defender to get selected that year. It’s interesting because NHL central scouting had three European defensemen ranked ahead of Seider but Yzerman skipped them all as well as a number of higher ranked forwards in order to get his man.

Seider played this season in the Swedish Hockey League (SHL), where he helped his club, Rögle BK, make it all the way to the Finals. He was a cornerstone for the team on the back end but also provided a great deal of offense. Seider had 7 goals and 21 assists in 41 regular season games. He had a goal and four assists in 13 games in Rögle’s playoff run.

The Bad – There’s no question that Yzerman is a fan of Valtteri Filppula. In 2013, Yzerman signed him to a five-year deal in Tampa Bay worth $25M. In 2019, Yzerman did it again, this time for the Red Wings. He signed Filppula in 2019 for two years with a $3M AAV. Unlike with the Lightning, Filppula didn’t deliver. Now, 37 years old, it appeared as though Filppula’s age finally caught up with him.

The Ugly – In October of 2019, Yzerman swung a deal with the Blackhawks to acquire Brendan Perlini. The hope was that the 12th overall draft pick of the 2014 draft would look as good as he did when he played for the Coyotes. Unfortunately for the Red Wings, he didn’t. In fact, Perlini struggled last year so mightily that he didn’t even play in the NHL this season. Instead, he turned to Europe to play for Ambrì-Piotta in Switzerland.

On the other side of that deal was Alec Regula. Detroit gave up a good looking prospect who could become a regular on the Blackhawks blue line as early as next season. Regula was fantastic for the London Knights last year and looked like he was able to fit in nicely this year in the AHL playing for the Rockford Ice Hogs.

The 6th Ranked GM – Bill Zito (Florida Panthers)

Bill Zito spent 2013-2020 as an executive with the Blue Jackets. There was a strong belief in Columbus that Zito would eventually become their general manager. Instead, the Florida Panthers poached him for themselves. It’s still early days for Zito who has only just begun to make his mark in Florida.

Zito’s transactions have been well regarded around the league. So much so that he was a finalist for this year’s GM of the Year Award.

The Good – Zito recognized that big changes were needed in Florida and wasted no time making them. He swung a deal to ship out Mike Matheson and Colton Sceviour for Patric Hornqvist. This deal didn’t just get a bad contract out of Florida but it also added grit to the roster.

Along with Anthony Duclair, who Zito signed to a one-year $1.7M deal, He also brought in Alexander Wennberg, Vinnie Hinostroza, Carter Verhaeghe, Radko Gudas, and Markus Nutivaara before the start of the season.

Though most fans won’t know his name, Zito also signed prospect Logan Hutsko, someone who has fought injury in college but has giant potential. Hutsko was drafted by the Panthers but didn’t sign right away. It was actually Zito that had him put pen to paper. Time will tell how that development goes.

The Bad – Zito and the Panthers lost two effective players in free agency Evgenii Dadonov and Mike Hoffman. To be fair to Zito, those losses can be hung on the former GM, Dale Tallon for not negotiating an extension or moving them prior to season’s end. However, it was still Zito who was at the helm when Dadonov signed with the Senators and when Hoffman signed with the St. Louis Blues.

The 5th Ranked GM – Marc Bergevin (Montreal Canadiens)

In May of 2012, the Montreal Canadiens hired Marc Bergevin to be their GM and Executive Vice President. That means he has over nine years on the job with the Habs. Not surprisingly, Bergevin is bilingual, fluent in both French and English.

The Good – Let’s be honest, the reason that Bergevin ranked so high is because of his team’s recent success. After just barely scraping into the playoffs, it’s shocking that the Canadiens made it all the way to the Stanley Cup Finals. However, Bergevin, the architect of the that squad deserves his due. He was even recognized by the league this season, becoming a finalist for the Jim Gregory General Manager of the Year Award.

Bergevin needs to also be commended for his ability to build up the team’s prospect pool. He was even able to secure ten new prospects at the 2019 NHL Draft, which included an important piece for the team’s future. Bergevin was was very fortunate that the Habs’ secret weapon, Cole Caufield, was available 15th overall in that draft. Bergevin certainly didn’t miss in selecting the sniper.

The Bad – Had the Habs not gone on their incredible run, it’s possible that Bergevin could have been on the hot seat this offseason, with the potential of being replaced. That’s because he has made some mistakes. One of his biggest errors was trading for disgruntled star Jonathan Drouin. To get the former third-overall draft pick, the Habs gave the Lightning defenseman Mikhail Sergachev and a second-round draft pick which Tampa later used to select goaltender Olivier Rodrigue.

Since the trade, Drouin’s value declined. He has become an insignificant player for Montreal but the same can’t be said about Sergachev with the Lightning. He was an important member of the team and a reason why they were able to win back-to-back Stanley Cups.

The Ugly – Karl Alzner only played a total of 95 games in the bleu blanc et rouge, which wasn’t exactly what Bergevin expected when he signed the D-Man to a massive deal in the summer of 2017. Alzner signed a five-year, $23.125M deal. After which, he played almost as many games with the Canadiens farm team as did with with the Habs. Each of Alzner’s 87 games with the Laval Rocket was a reminder for Bergevin that he had made a big mistake. Things were so bad that Alzner needed to be bought out of the final two years of that deal.

The 4th Ranked GM – Joe Sakic (Colorado Avalanche)

There is another executive that took the Yzerman route to become an NHL GM. Like Stevie Y,  Joe Sakic had a Hall of Fame career as a player all with just one organization, the one he now manages. Sakic was already a legend in Colorado, having played 20 seasons for the organization between the Quebec Nordiques and the Avalanche, when he became a Senior Advisor in 2011. Sakic worked his way up to become the Executive Vice President and then landed his current role as the GM a year later. He will have been doing the job for seven years this September.

The Good – The Avalanche play some of the most exciting and dynamic hockey in the league thanks to the way their roster has been constructed. A big part of that is thanks to Sakic’s draft record and ensuring that he had Nathan MacKinnon locked up on a seven-year $44.1M contract. That deal is incredible for Sakic and the team as MacKinnon left a lot of money on the table.

The best move that Sakic ever made is without a doubt, the three-team trade he made in 2017 with the the Senators and Predators to unload Matt Duchene. That move enriched the Avs to the tune of a second round draft pick in 2018 (traded to Florida for a pair of picks (Justus Annunen and Danil Zhuravlyov), a first (Bowen Byram) and a third round pick in 2019 (Matthew Stienburg), Samuel Girard, Vladislav Kamenev, Shane Bowers, and Andrew Hammond.

This was a massive win for Sakic. Girard has been excellent for the Avalanche and has become one of the team’s most reliable defensemen. There is also still a lot to be seen from this trade. Bowers is still just a 21 year old prospect but has looked good in the AHL. Byram is 20 and after proving that he’s too good for the WHL has already played 19 games for the Avalanche. Stienburg, Annunen, and Zhuravlyov still have a chance to make the NHL but it may not be an easy road for them.

The Bad – Sakic has made a few blunders such as when he allowed Paul Stastny to walk as an unrestricted free agent at the end of the 2013-14 season without getting anything in return for him. One of his bigger mistakes was the contract that he gave to Francois Beauchemin. At the time, Beauchemin was 35 years old. Beauchemin cashed in by inking a three-year, $13.5M deal with a $4.5M AAV and a no movement clause. The deal was so bad that Beauchemin didn’t play all three seasons. Sakic was forced to swallow his pride and buy out the defenseman.

The Ugly – Worse than the mistake Sakic made with Beauchemin is the one he made with Brad Stuart. Sakic traded for the blue liner in 2014. The transaction gave the Sharks a second round draft pick in 2016 (used to select Cameron Morrison) and a 6th round draft pick in 2017 (used to select Denis Smirnov).

The trade wasn’t so bad on its own. It got ugly when Sakic extended Stuart prior to the start of the season, before Stuart was even able to play a single game in an Avs jersey. Sakic gave him a two-year $7.2M contract that carried a $3.6M cap hit. Once again, Sakic had to fix his own mistake by buying out Stuart in 2016.

The 3rd Ranked GM – Doug Armstrong (St. Louis Blues)

In 1992, the Minnesota North Stars hired Doug Armstrong to be their Assistant General Manager. Since then, he’s been an NHL mainstay. He worked his way up to be the GM of the Stars before changing organizations to be the Director of Player Personnel of the Blues. Once again, he climbed the ranks within the franchise to become the team’s GM, taking the job in the summer of 2010. Armstrong’s been the Blues GM for 11 years and the franchise’s President of Hockey Operations for nearly eight years.

The Good – Without a doubt, being the architect of a Stanley Cup winning team is Armstrong’s biggest feat. It’s actually something he’s done twice. He won the Mug in 1999 with the Stars and did it again with the Blues in 2019. (It has no bearing on these rankings but Armstrong is actually the only member of the Double Triple Gold Club for winning those two NHL championships as well as Olympic gold in 2010 and 2014 and the World Championship in 2007 and 2016.)

In order to win the 2019 title, Armstrong made a wise but risky trade. He moved Patrik Berglund, Vladimir Sobotka, Tage Thompson, and a first and second-round draft pick for Ryan O’Reilly. It was a lot to give up but it turned out great for Armstrong and the Blues. As we know, the team won the Cup thanks in part to O’Reilly’s strong play. It was good enough for O’Reilly to take home the Frank J. Selke Trophy as the best defensive forward and the Conn Smythe Trophy as the playoffs MVP.

The Bad – Armstrong might be a wizard when it comes to unloading bad contracts. It’s a skill he’s acquired because he has a knack of overpaying players. It’s something Armstrong has done too many times. Jori Lehtera was signed for three-years at an average salary of $4.7M and then dumped in a trade for Brayden Schenn.

Berglund had the same fate. Armstrong signed him in 2017 to five-years for $3.85M. Berglund’s awful contract was sent to Buffalo as a part of the O’Reilly exchange. Berglund’s ticket wasn’t the only one dropped on the Sabres in the O’Reilly trade. Armstrong also included Sobotka because he had foolishly given the Russian a three-year $3.5M contract.

The Ugly – For some reason, in 2014 Armstrong felt like he needed a premiere goaltender even though he already had Jaroslav Halak and Brian Elliott on his roster. Instead of rolling with the tandem, Armstrong decided to ship Halak with a first-round draft pick in 2015 (which was later traded to Winnipeg who selected Jack Roslovic), a third-round pick in the 2016 draft (that was traded to Florida who selected Linus Nassen), William Carrier, and Chris Stewart to the Sabres for their new preferred stopper Ryan Miller and center Steve Ott.

Miller’s save percentage in his only season in St Louis was .903 and .897 in the playoffs. He left at season’s end to sign as a UFA with the Canucks. That same season, Halak was flipped to the Capitals where he had a .930 save percentage in the regular season but the team didn’t qualify for the playoffs. Armstrong would have been much better off having done nothing instead of swinging for the fences with this trade.

The 2nd Best GM – Lou Lamoriello (New York Islanders)

This one stings for Leafs fans but one of the best general managers in the NHL is Lou Lamoriello. He was honoured as such with his second GM of the Year Award in as many seasons. It’s very impressive for a general manager who has only been with the Islanders for three seasons. Lamoriello isn’t new to winning. He was actually the general manager for the Devils when they won Stanley Cups in 1995, 2000 and 2003.

The Good – Lamoriello’s best move in his time with the Islanders was to identify and hire a new coach, Barry Trotz. Fresh off winning a Stanley Cup with the Capitals, Trotz resigned from coaching in Washington and was quickly recruited by Lamoriello. Trotz was paid his worth to join the Islanders and it’s been a successful partnership. The coach has had his players buying into his system, which has proven to result in his squad playing tremendous defense-first hockey.

The Bad –  Lamoriello uses his experience to target the players he’s familiar with to improve his teams. That’s why, when he got to Long Island he brought in a pair of Toronto Maple Leafs he worked with while in Toronto. He signed fan favourite Leo Komarov and traded for Matt Martin. Lamoriello even traded for Travis Zajac who he drafted back in 2004 to the Devils. Just because he knows the players doesn’t mean it’s always a good fit.

Cap management is an area where Lamoriello struggles. Too many of his contracts overpay players and even include too much term. This is true about Komarov who was paid $12M to play with the Islanders for four years. Martin was also given a four year term in the deal he signed in New York. The list of Lamoriello’s overpaying contracts is long. Anders Lee was given a seven year deal with an annual cap hit of $7M. Brock Nelson was handed six years with a $6M AAV. Jordan Eberle was signed for five years at a $5.5M cap hit. Semyon Varlamov was paid four years at $5M per season.

Due to those contracts, Lamoriello was forced to make other roster decisions such as trading away Devon Toews. When there isn’t enough cap space, moves like shipping out a valuable defenseman need to happen. That’s why Lamoriello shipped Toews to the Avalanche for a pair of picks.

The Ugly – While it’s difficult to pin this squarely on Lamoriello, the organization lost its franchise player, Tavares, on his watch. While Tavares may have just wanted to play for his hometown and favourite team, he wasn’t impressed enough by the Islanders’ pitch during free agency to remain with the team that drafted him. Despite the success the Islanders have had without their former captain, it is still a big loss.

The Best GM – Julien BriseBois (Tampa Bay Lightning)

When the Lightning promoted Julien BriseBois in September of 2018, there’s no way they could have expected the level of success he’d provide. In his first season as GM, the Lightning were eliminated from the postseason without even winning a single game. BrisBois was sure to make the necessary changes to ensure that wouldn’t happen again. The team went on to capture back-to-back Stanley Cups.

The Good – BriseBois can be celebrated for a number of trades that have worked out for the club and helped them win hockey’s biggest prize. He swung deals to get Pat Maroon, Blake Coleman, and Barclay Goodrow who all helped the Lightning in both title runs. As wise as those acquisitions look now, it’s actually the move that BriseBois didn’t make that may be his best.

BriseBois hired Jon Cooper in 2010 to coach the Lightning’s AHL affiliate, the Norfolk Admirals. In his second year on the job, Cooper won the Calder Cup. He earned a promotion to the NHL a year later and had been coaching the Lightning for five season before BriseBois became the GM. When the Blue Jackets, as an eighth seed, beat the Tampa in four straight games to knock them out of the 2017-18 playoffs, it could have cost Cooper his job. Instead, BriseBois was patient and let his coach know that his job was secure. Keeping Cooper turned out to be an excellent decision.

The Bad – It’s difficult to be overly critical of the moves BriseBois has made but one of them is likely to eventually become a burden on the team even though it has paid off in the short term. In the summer of 2019, BriseBois locked up star goaltender Andrei vasilevskiy to an eight year $76M contract. It comes with a $9.5M cap hit that will remain on the books until the completion of the 2027-28 season. It’s a giant investment that historically doesn’t work out for goaltenders. While there is a chance that down the line the deal will be seen as a good one for the organization, we won’t know for sure for several years.

The Ugly – The Maple Leafs are often accused of salary cap manipulation but it was BriseBois who was investigated this season for it. Though the NHL found no wrongdoing, it seemed very suspicious that the 2018-19 Hart Trophy winner, Nikita Kucherov, was on the long-term injured reserve (LTIR) for the entire 2020-21 season only to return for the playoffs. By keeping Kucherov off the payroll, BriseBois was able to use his star’s $9.5M cap hit as added space to make additions to the roster. Then, when the playoffs began, somehow Kucherov was no longer injured, When he took to the ice he looked like the All-Star he is. Perhaps it’s a coincidence or maybe it’s not.

2020-21 was a wild ride in the NHL. The GMs now have it in their rear-view mirror and will be looking forward to next season. Hopefully Dubas and the Maple Leafs make all the right moves to allow him to ascend to the top of these rankings this time next year.