Toronto Maple Leafs 2016 NHL Entry Draft Retrospective

The 2016 NHL Entry Draft will always be remembered as the one where the Toronto Maple Leafs selected Auston Matthews.

Some believe the 2014 NHL draft was the turning point for the Toronto Maple Leafs rebuild but the 2016 draft was where the Leafs were supposed to set themselves up for the next decade or so. 

They had successfully bottomed out, tanking to the bottom of the standings and winning the draft lottery for the first overall pick and the right to draft American born star forward Auston Matthews.

The Leafs were walking into Buffalo where the draft was held with 11 picks in hand.

Two firsts (first and 30th), two seconds (31st and 57th), two thirds (62nd and 72nd), two fourths (92nd and 101st), one fifth (122nd), two sixths (152nd and 179th), and one seventh (182nd).

More than enough draft capital to add to their burgeoning prospect cupboards. 

On day one of the draft, the Leafs ended up swapping their later first, the 30th overall pick and a 2017 second rounder to the Anaheim Ducks for goaltender Frederik Andersen.

They quickly locked up their goalie of the future to a five-year contract extension worth $5 million per year. 

Toronto Maple Leafs 2016 NHL Entry Draft Retrospective

First Pick

There were some whispers heading into the draft, trying to create a debate that maybe Finnish winger Patrik Laine could push himself into the conversation for first overall.

This was largely due to great success on the international stage where the Finnish U-20 team won the World Juniors and Laine lead Finland en route to a World Championship silver medal win, capturing the tournament MVP.

However, it was never really a debate that Auston Matthews would be the first overall pick and thankfully cooler heads prevailed.

Eight years later with a Calder Trophy, Hart Trophy, Ted Lindsay Award, and three Rocket Richard Trophies, Auston Matthews was hands down the correct choice.

He is on pace to go down as the greatest Toronto Maple Leaf of all-time, a first ballot Hall of Famer and possibly the greatest goal scorer of his generation and one of the greatest of all-time.

No player comes close to the impact that Matthews has had thus far and short of winning a stanley cup, and international stage performance, there isn’t much more he can do to prove this.

He has the obvious goal scoring prowess but he is also one of the better forwards in the league defensively. There has not been a moment since his four-goal debut that should have made anyone question whether or not Leafs brass made the right call.

Third Pick

With the 57th overall selection, the Leafs chose feisty Swedish winger Carl Grundstrom.

None of the players mentioned as candidates before were available and he himself was slated to go in the early-mid second round so getting him near the end was looked at as a solid selection.

He did not seem to have game breaking ability but he showed promise to be a decent third line forward. 

After a couple more seasons in the SHL, Grundstrom would finally make the move to the Marlies where he showed a lot of promising producing 13 goals and 29 points in 42 games in his first North American season.

But partway through, he would be shipped out as part of a package to the LA Kings for stud blueliner Jake Muzzin.

Since then, he has mainly stuck as a bottom-six forward for the Kings and although not hitting his projected ceiling, he has shown to be a capable NHLer logging over 200 games in the NHL.

Both from an actual career standpoint as well as value to the Leafs, this has proven to be a good pick in hindsight. 

Fourth Pick

The fourth pick by the Leafs came in the third round at 62nd overall where the Leafs took Boston College commit, goaltender Joseph Woll.

He had drawn stylistic comparisons to Carey Price for his calm demeanor in the crease and his ability to stay square to shooters. He would immediately step in as the program’s starting goalie that next year.

Over his three years, he would steadily progress from a .913 SV% to a .919% in his final season.

He would then sign his ELC with the Leafs and start his career with the Marlies. Over the next few seasons he would hone his craft, once again showing steady improvements before making the jump to the NHL on a full-time basis this past year.

Despite playing NHL games over three years, Woll has only 36 career regular season games under his belt so far and seven playoff games.

In that time, he has been northing short of stellar posting a .912 SV% in the regular season and .940 SV% in the postseason. 

The Leafs have not had a true homegrown starting goalie since James Reimer, though Garret Sparks did play 37 games. As of right now, it's possible that Woll is the Leafs starter next year.

He has been a great pick for the Leafs and if he can maintain his play, could go down as one of the Leafs best homegrown goalies of the last 40 years or so.

Fifth Pick

The Leafs used their second pick in the third round at 72nd overall to once again reach for size in the form of 6-4 defender J.D. Greenway.

He was slated to go in the mid-fourth or fifth round but you can’t teach size, so the Leafs nabbed him up early.

He had shown some flashes of offensive potential and had decent mobility for a defender his size and despite that size, he was not known to be a big bruising defender.

As most players taken in this stage, Greenway had parts of his game that needed to be smoothed out and refined, which he was going to do at the University of Wisconsin.

After two seasons there where he underwhelmed, he went to the USHL and then re-committed to the University of Maine.

At the NCAA level, Greenway struggled to remain consistent, which was an issue that had plagued his career. His performance and lack of large steps forward made the Leafs let his rights expire where he signed signed a minor-league contract with the Boston Bruins AHL affiliate, the Providence Bruins. 

This past year he signed with the ECHL’s Greenville Swamp Rabbits but was listed as a forward. He has seemed to find success as a minor-league option but that was not what the Leafs had hoped for when taking a chance on him nearly two rounds earlier than his projection. 

Sixth Pick

At 92nd overall in the fourth round, the Leafs once again opted to take a double-overage player in Regina Pats forward, Adam Brooks.

Coming off a season where he scored 38 goals and 120 points in 72 games, the 20-year-old Brooks had impressed Leafs management to take a flyer on him.

As I said, Brooks was twice passed over and the only ranking of him I could find was the 176th ranked North American skater by NHL Central Scouting in 2015.

This begs the question, couldn’t the Leafs had just waited to nab him up a couple weeks later when he likely would have went undrafted?

Or even taken him in the sixth or seventh round? Yes, that was many people’s complaints at the time. Regardless, the Leafs wanted to ensure he was in the organization. Brooks would spend the following year back in Regina where he put up an even better 43 goals and 87 assists for 130 points in 66 games.

He then turned pro, joining the Marlies and winning a Calder Cup in his first season. The following year with the promotion of multiple key Marlies’ forwards, he took over as a main player scoring 21 goals and 40 points in 61 games.

The year after, he saw his first taste of NHL action playing seven games and firmly placing himself as a main call-up option for the Leafs. Then in 2020-21, he played 11 games scoring five points for the Leafs, splitting time with the Marlies once again.

2021-22 saw what must be the most bizarre waivers scandal in recent memory with him being claimed off of waivers four separate times, including being reclaimed by the Leafs.

All-in-all he played 25 NHL games with three different teams that year. He was signed by the Philadelphia Flyers in the 2022 off-season where he currently remains  as a minor league fixture for them and is slated to become an unrestricted free agent. 

Although not a bad pick necessarily, with him at least playing 43 NHL games and still being somewhat relevant to the league as a possible call-up option.

At 92nd overall, there was clearly some value left on the table with the Brooks pick. It’s tough to be too upset though because again eight years out there is still a chance he could surpass 100 games. 

Seventh Pick

With the 101st pick, the Maple Leafs selected 6-6 235lbs left-handed defender from the Saginaw Spirit of the OHL, Keaton Middleton.

He showed very little in terms of offensive potential and unsurprisingly, was seen as a punishing shutdown defensive blueliner.

He spent the next two seasons as captain of the Spirit and in his final OHL year reached career highs four goals and 24 points in 64 games. Of course, points don’t paint a clear picture when it comes to defenders, especially in his case. 

Following his juniors career, he signed a two-year AHL deal with the San Jose Barracuda. There, he once again failed to show a lot in terms of offense but was given a two-year entry-level contract by the Colorado Avalanche in 2020.

He would suit up for three games with the Avs that season and has spent the past four years in the organization, playing primarily with their AHL affiliate, the Colorado Eagles.

His current deal is set to expire next year and it seems like even at it’s conclusion he will be a mainstay in the North American minor league circuit.

Eighth Pick

In what ended up being a draft filled with overage players for the club, the Leafs took their third in Russian winger Vladimir Bobylyov at 122nd overall. He spent the previous two seasons playing in the WHL and after a poor draft year showing of nine points in 52 games, he exploded for 67 in 72. 

Despite his relatively mediocre production, he had interesting tools at 6-2 and 200lbs along with solid skating and a powerful shot, there was a decent framework to build from. He spent the next season back with Victoria Royals but ended up going back to Russia midway through the year to join Spartak Moscow of the KHL. 

Since then he has lived the life as a journeyman player bouncing between different organizations in Russia. He has spent the majority of his career in the second-tier VHL as a secondary offensive option for various clubs.

Ninth Pick

The next pick at 152nd overall was another overager and teammate of Bobylyov, Jack Walker. He had started his junior career as a defender before transitioning to forward and was passed over twice before the Leafs selected him.

One skill that made Walker intriguing was his skating and speed, which he coupled with his puck-skills to generate offense producing 36 goals and 84 points in 72 games that season.

He was seen as a late bloomer who after taking time switching positions was able to come into his own. The next season would see some regression in production scoring only 72 points in 70 games.

That summer, he would sign an AHL contract with the Iowa Wild where he mainly played with their ECHL affiliate the Rapid City Rush. He would spend the next few seasons bouncing between the ECHL with various teams as well as Denmark’s Metal Ligaen. Since then, he has bounced between various European leagues, most recently in France’s Ligue Magnus. 

Tenth Pick

At 179th overall, the Leafs went again with size, drafting big-bodied London Knights’ defender Nicolas Mattinen.

However, he had shown some offensive potential with 10 points in 39 games in his rookie OHL year. The following year would see some regression in that aspect but in the next two years split between the Flint Firebirds, Hamilton Bulldogs, and Oshawa Generals he would breakout offensively. He would play 132 games scoring 26 goals and 91 points.

Despite his progression, the Leafs would not sign Mattinen and his rights would expire, setting the stage for him to join the Canadian Usports University of Ottawa.

In his third and final year, Mattinen would win USports MVP, Defenceman of the year, and be named an all-Canadian first team all-star. He would then play eight games with the Laval Rockets of the AHL before heading to the Latvian ICEHL and Germany’s DEL. 

At the conclusion of this past season, it was announced that the Leafs had signed Mattinen to a one-year, two-way league minimum contract for the 2024-25 season.

Eleventh Pick

At 182nd overall and with their final pick of the draft, the Leafs selected their fifth overage and third Russian player, Nikolai Chebykin. Like many players in this class, the first noticeable attribute that he possess is his size at 6-3.

Aside from this, he played a powerforward game using his size and decent skating to his advantage. His 35 points in 39 games in the Russian MHL did not jump off the page but he seemed to have tools to translate his game well. 

Despite coming over for a few development camps, Chebykin never left Russia, working his way up from the MHL to the second-tier VHL and now to the KHL. 

Conclusion

I mentioned this before but in a draft following a tank year, where you have 11 picks, you should be able to get at least a few impact players.

The goal would be to set your team up with players that will help supplement your budding core and help fill out your depth for much of the next decade. Unfortunately, this did not happen for the Leafs.

Of course the first overall Auston Matthews is a franchise player but outside of him, there has not been much to show for. Grundstrom was a piece in the Jake Muzzin trade but even he has not been much more than a fourth line player at the NHL level.

Joseph Woll looks very promising as a potential starter but even in his case there is some uncertainty. He has less than half a season’s worth of games under his belt and it should not shock anyone if he does not pan out longterm.

Outside of those three, nobody appears to have a guaranteed NHL job going forward with only two of the 11 picks having played over 50 NHL games.

In hindsight, the 2016 draft was a pretty colossal failure outside of the first overall pick and even at the time there were warning signs.

An over reliance on size and overage players as well as a few reaches seems to be the most glaring issues. Aside from that, a lack of swings for potential hurt the Leafs chances of coming out of the draft with steals. (stats and info from from nhl.com, capfriendly.com and hockeydb.com).

This lack of NHL talent extracted from the draft forced the team to sign free agents and make trades to fill out their roster, setting the Leafs back years and has harmed the team a great deal.