Ranking the Top 5 Biggest Toronto Maple Leafs Trades of the Decade
The Toronto Maple Leafs have executed multiple trades from 2010 until the end of 2019. We have compiled the top five trades of the decade.
In a decade full of Toronto Maple Leafs playoff disappointments, the club has been fortunate enough to have had some stellar talent pass through. Always bound by the NHL salary cap, the Leafs have managed to both acquire and ship out big names.
We have evaluated ten years’ worth of trades and narrowed them down to the top five. These are the most impactful transactions the organization has seen over that span.
5. Zach Hyman for Greg McKegg
There have been many trades that took place over the decade, but perhaps the most one-sided transaction was the deal that landed Auston Matthews his longtime linemate, Zach Hyman. All it took to get him was a player who had played a total of four games in the NHL at the time, Greg McKegg.
On June 19, 2015, the Leafs and Florida Panthers swapped prospects. The circumstances were right for the deal since Hyman, who was a fifth-round pick of the Panthers, refused to sign with the team unless they were willing to provide him an NHL job. They were not.
Playing for the University of Michigan, Hyman had just come off winning the 2014-15 Michigan Athlete of the Year award after tallying 54 points in 37 games. He was also a top-10 finisher for the Hobey Baker award. Instead, it rightfully went to Jack Eichel who recorded 71 points in 40 games.
McKegg was a third-round pick of the Leafs. The six-foot center had scored 19 goals and 28 assists in 65 games for the Marlies in 2013-14 and followed that up the next season with 22 goals and 15 assists in 62 games. It appeared as though McKegg might be someone who could put the puck in the net at the next level. He did. In his career, he has scored 14 NHL goals.
McKegg became a journeyman in the NHL. He has spent seven years bouncing back and forth between the AHL and NHL. In that time, he has played for six different organizations. Hyman has now been with the Leafs for five years and has scored 130 points including potting 59 goals.
4. Nazem Kadri for Tyson Barrie and Alexander Kerfoot
Nazem Kadri was a much-maligned member of the Toronto Maple Leafs. Early in his career, he was criticized by his coaches Dallas Eakins and then Ron Wilson for his perceived lack of work ethic and conditioning. He was often characterized as being lazy both at and away from the rink.
At the end of his tenure with the Leafs, Kadri was once again crushed by his detractors. This time it was a result of the early exits he made from postseason play due to the reckless actions that led to his suspensions. Despite all the criticism, Kadri was an important member of the Leafs core.
In April of 2016, Kadri signed a six-year team-friendly deal worth a total value of $27 million. That deal only got better as the centerman produced offensively the way that Leafs brass always knew that he could.
On July 1st, 2019, the Toronto Maple Leafs and Avalanche swapped high-level talent. The Leafs gave up a player in Kadri who some considered to be worthy of the captaincy on a sweetheart contract in exchange for two players who help the current iteration of the Leafs.
Toronto got Alexander Kerfoot and Tyson Barrie for Kadri. The contracts and cap hits of all three of these players played a significant role in executing the transaction. Colorado retained 50 percent of Barrie’s annual average salary of $5.5 million to get the deal done.
The Toronto Maple Leafs also aren’t expected to keep Barrie beyond this season because he is set to be an unrestricted free agent and he could demand compensation that Toronto cannot fit under its cap.
Kerfoot, however, should have a longer stay in Toronto. According to CapFriendly, he has a $3.5 million AAV and is locked up until the end of the 2022-23 season thanks to the four-year deal he received from Kyle Dubas in the summer.
3. James van Riemsdyk for Luke Schenn
In a draft-day deal that the Philadelphia Flyers certainly regret, they were fleeced into giving up a former second-overall draft choice in exchange for a defenseman who never reached his potential.
On June 23, 2012, the Maple Leafs picked up James van Riemsdyk in exchange for Luke Schenn.
It was a swap that the Toronto Maple Leafs general manager Brian Burke and Flyers GM Paul Holmgren had been working on for months. The deal finally got done on the second day of the 2012 NHL draft.
The Flyers gambled that Schenn would be a pivotal part of their blueline and reuniting him with his brother Brayden would elevate both players.
They were willing to part ways with a 23-year-old van Riemsdyk to do make that happen. They felt that van Riemsdyk was expendable because of the injuries that had plagued him the previous season, limiting him to only 43 games.
JVR became one of the Toronto Maple Leafs best players throughout his entire stay with the team while Schenn eventually found himself in the bottom pairing in Philadelphia. As a stay-at-home defenseman who wasn’t able to elevate his game in the NHL, the Flyers never got the value they hoped from Schenn.
JVR spent six years with the Leafs before the salary cap kept them from extending him. In that time he played 413 games and picked up 294 points.
That included his 2017-18 campaign when he scored an impressive 36 goals. He was known to set up shop near his opponents’ net and use his impressive hand-eye coordination and quick release to pick up goals in bunches.
Van Riemsdyk was one of Toronto’s best wingers of the decade and it’s all thanks to this mega deal.
2. Frederik Andersen for Picks
On June 20, 2016, the Toronto Maple Leafs pulled the trigger on who they identified as the goalie of the future.
General manager Lou Lamoriello was willing to give the Anaheim Ducks a 2016 first-round and a 2017 second-round pick to acquire Frederik Andersen.
Prior to Andersen, coach Mike Babcock didn’t have a clear starter.
He spent the previous season, 2015-16, splitting time between stoppers Jonathan Bernier and James Reimer.
Bernier played 38 games and Reimer 32 that year. Garrett Sparks also took to the crease in 17 games that season. When Andersen arrived, there was no longer any question about who was the Toronto Maple Leafs primary goalie.
The Ducks at this point had identified John Gibson as their go-to starter and as such were shopping Andersen.
The Leafs were happy to get him as he solidified himself as the best stopper the franchise has had this decade.
Gibson has gone on to play seven years with the Ducks and is still their number one goaltender. He started 257 games in that time and earned 131 wins. In Andersen’s seven years in the NHL, he has 203 wins in 337 games started.
The Leafs 2016 draft pick was used by Anaheim to get center Sam Steel and the Ducks turned the 2017 second-round pick into left-winger Maxime Comtois.
Meanwhile, Andersen spent four years of the decade with the Toronto Maple Leafs, playing 224 games and accruing a .917 save percentage with a 2.74 goals-against average.
Now, as one of the most heavily used goaltenders in the league, Andersen is a key member of the current Leafs roster.
He has even received his first All-Star Game nod this season. The Buds hope that Andersen will help the team achieve greater future playoff success than they had throughout the decade.
1. Phil Kessel for Kasperi Kapanen
The Toronto Maple Leafs were involved in two blockbuster trades involving Phil Kessel.
The first was the deal to bring him to Toronto that fell just outside the decade. That transaction spearheaded by Burke brought Kessel to the blue and white in exchange for a 2010 first-round pick (second-overall: Tyler Seguin), and a second-round pick (32nd overall: Jared Knight) along with a 2011 first-round pick (ninth overall: Dougie Hamilton).
The biggest deal of the decade for the Leafs was Kessel’s second trade, the one that sent him to the Pittsburgh Penguins. On July 1, 2015, after six seasons, scoring 181 goals, adding 213 assists for a total of 394 points in 446 games, the Leafs pulled the trigger to ship Kessel out of town.
The trade triggered what was widely considered to be a rebuild for the Leafs.
By moving the sniper, the Buds not only got a decent return, but also freed up cap space, which also has significant value in the NHL. Ahead of the 2014-15 season, Kessel signed an eight-year extension worth $64 million. When the Leafs traded him, his annual cap hit was eating $8 million of the team’s cap. They were anxious to get that substantial AAV off their books.
The Penguins gave up Kasperi Kapanen, Scott Harrington, Nick Spaling, a 2016 conditional first-round pick and a 2016 third-round pick to get Phil Kessel, Tim Erixon, Tyler Biggs, and a 2016 conditional second-round pick.
The jewel among the three players the Leafs received is Kapanen. He has been phenomenal for Toronto and has even spent time on the team’s top line. Getting a young, highly-skilled winger to develop with the Leafs made the trade retrospectively even better.
The Penguins were happy with what Kessel brought to their team. He played four years in Pittsburgh and even had a career-best 92-point season. More importantly, he helped the team win back-to-back Stanley Cups in 2016 and 2017.
The Leafs took advantage of the cap space they opened up and used it to help put together the team that they have now. Moving Kessel was the linchpin to the current construction of the team and the most important trade the Leafs made this decade.
It allowed them to finish last and draft Auston Matthews, and they turned one of the picks into Freddie Andersen.
Next. Top 10 Meaningful Goals of the Decade. dark
We hope that all the moves that took place over the decade lead to bigger and better things in this next decade to come. Most importantly, hopefully, the 20s include a parade down Yonge St with the Stanley Cup.