The Toronto Maple Leafs have been the laughing stock of the NHL for quite some time now. It’s a hockey-crazed city, perhaps the biggest NHL market today, and they haven’t won the Stanley Cup since 1967. They’ve made the Playoffs the last 8 years in a row and have never made it past the second round.
This is the final installment of 3 Part Series on the Maple Leafs. Part 1 takes a look at what the problem was. Part 2 looks at some scenarios and ways we can improve but the final installment, Part 3, will be about actual events how the Leafs get better today and how we go about re-assembling them to become Stanley Cup champions.
TABLE OF CONTENTS
In Part 1 and Part 2 we take a much deeper dive into this but to summarize the Leafs problems are the D-corps inability to defend, inconsistent goaltending and how the core four forwards (Auston Matthews, Mitch Marner, William Nylander and John Tavares) don’t ever seem to rise to the occasion when it matters most.
Year-over-year the Leafs have turned to free agency and in-season deals to raise the bar in hopes of winning a Stanley Cup. GM’s Brad Treliving, Kyle Dubas and Lou Lamoirello have had their fair share of wins and losses in free agency and trades but none of them have had the guts to pull off a trade of real significance. They’ve lived and most of them have died on the Core 4 and it hasn’t materialized to anything of significance. It’s time for a change. The core must be restructured, so let’s look at how Toronto can do this.
Before we look at some trades Toronto can make right now. Let’s look at the past. What can we learn from past trades?
It’s not difficult to trade a star player in the NHL because this occurrence isn’t rare. Erik Karlsson was traded last year to the Pittsburgh Penguins and he carried a whopping $11.5 million AAV contract for 3 more years and was 33 years old at the time. Acquiring a Nylander or a Matthews is a lot more appetizing than this. Vegas’s acquisition of Jack Eichel was also huge. They gave up promising young guns Alex Tuch and Peyton Krebs, plus a first and second-rounder.
With history on our side, it’s easy to see that star players get traded all the time, so why haven’t the Leafs done this yet? The reason why is that the Leafs are in win-now mode. The two deals mentioned above, the teams who gave up the star players, the San Jose Sharks and the Buffalo Sabres, these teams were losing and they wanted a jumpstart on their rebuild. San Jose traded Karlsson away preceding the latest 2023-24 NHL season and they finished dead last. The Buffalo Sabres haven’t made the playoffs in the last 13 years and it seems like they don’t know how to re-write the ship.
It’s a lot easier to trade a star player for the future. Every team has draft picks and promising prospects in their pipeline that they can deal away. The majority of teams in the NHL can be placed into two categories. They’re those in win-now mode and want to get better today, so they trade draft picks and prospects and spend to the salary cap to win. The others are losing today and want to get better tomorrow. They get rid of players in their prime today who can yield the highest return so they can win in the future. They get worse today in hopes of a better future.
The Leafs find themselves in a peculiar spot. They’re good right now. They’re winning. Their regular season record proves this. But there is a problem. They’re not winning in the post-season when it matters most. Goalies, front office, upper management and depth forwards have all changed drastically over the past 8 years but the only thing that hasn’t is Nylander, Matthews and Marner so something must change and it revolves around them. A team that trades away a star player is usually worse following the trade. What the Leafs want to pull off is a trade of a star player that makes them better today, and what combination of players is better than a Mitch Marner or William Nylander? Right now I don’t think there are more than 10 players better than him and 6 or 7 of those players are forwards, who the Leafs don’t need more of. So, pulling off a trade of this magnitude won’t be easy.
Before diving into what a trade could look like, let’s look at some past trade comparables from which we can draw inspiration. Within the NHL and outside.
Kawhi Leonard to the Toronto Raptors in 2019
Toronto receives: Kawhi Leonard and Danny Green
San Antonio receives: DeMar DeRozan, Jakob Poeltl and a top-20-protected 2019 first-round pick.
This is a trade that I’m sure most of Toronto remembers quite fondly. Kawhi Leonard was a top 5 player in the NBA, an absolute superstar. However, after leading the Spurs to a championship in 2014 they struggled moving forward and after an injury-plagued 2017-18 season which saw Kawhi only play nine games he was dealt in the off-season.
The Raptors on the other hand were in a situation that could be compared to the Leafs. They were having year-over-year success in the regular season, having easy access into the playoffs in the playoffs. The Raptors were led most notably by all-star guard DeMar DeRozan, guard Kyle Lowry, and forward Serge Ibaka. However, they weren’t winning and change was needed.
With hindsight, Toronto will consider Masai Ujiri’s trade as exactly what the doctor prescribed – change needed to happen. Toronto won a championship with Kawhi and everything turned out the way it was supposed to, but if Toronto floundered and lost in the 1st or 2nd round as they typically did, this was a dumb trade. DeMar DeRozan had two years left on his deal, he loved Toronto and was in the prime of his career. Toronto hadn’t seen a star like him since Chris Bosh or Vince Carter. Kawhi Leonard was a superstar but didn’t play in the past year due to injuries and was on an expiring contract and was a sure bet to not re-sign in Toronto leaving the Raptors with no chance of winning beyond this year. DeRozan offered comfort and a winning formula for at least a few more years while Kawhi was a one-and-done arrangement.
Something that many of us don’t consider is the business side of running a professional sports team. The Raptors and the Leafs are a business and the primary goal is to make money, and the best way to do this is to win. Winning brings attention which results in ticket sales, endorsements and advertisements. If the Raptors had kept DeRozan they would’ve guaranteed high revenue for a longer period which is something that Ujiri and all GMs must consider. So, there was more risk involved with this than what meets the eye and what makes this decision by the Raptors all the more bold and outlandish.
The Leafs are in a very comparable situation right now. Marner might be a bigger name in the NHL than DeRozan is in the NBA but Marner is just one of the stars on the Leafs while DeRozan was THE star with the Raptors. The Raptors didn’t get worse when making this trade even though they traded away their star player. They gave DeRozan along with a young player and a 1st-round draft pick for a superstar (Kawhi Leonard) and a role player (Danny Green). They forfeited the future assets in this deal but I guess that is the cost you pay for an NBA championship.
Cleveland trades Kyrie Irving to Boston in 2017
Boston receives: Kyrie Irving
Cleveland receives: Isaiah Thomas, Jae Crowder, Ante Zizic, Brooklyn’s 2018 1st-round pick (unprotected) and Miami’s 2020 2nd-round pick.
This trade is a good example of what can go wrong when trading away the best player. Cleveland was one year removed from winning an NBA championship when star guard Kyrie Irving wanted to make a name for himself without the help of King James (LeBron James).
Irving spent two years in Boston championship-less while the Cavaliers advanced to the NBA finals. However, being Kyrie-less was a big problem as they were swept in four games by the Golden State Warriors.
The acquisitions the Cavaliers gained from this trade didn’t live up to expectations. The All-Star guard Isaiah Thomas only suited up for 15 games due to injuries. Crowder and Zizic were nothing more but role players and the two draft picks didn’t materialize to star NBA players, although 2018 1st-round pick, Colin Sexton, is an adequate and well-performing NBA player and probably will be for years to come. However, he can not be held in the same breath as Kyrie Irving.
In my opinion, the Irving scenario is much more likely to occur than the DeRozan/Leonard scenario. When you trade away the best player you will typically lose the trade. No one could’ve predicted how bad Isaiah Thomas turned out. However, when trading away the best player draft picks will always be received and these picks rarely become star players.
Toronto media outlets consistently fire up a storm against Marner for his lack of playoff performance but this guy has been more than a point-per-game player in the last 6 years of his 8-year career. If this is what the media complains about this is a good problem to have. How badly could Mitch be if he’s putting up these stat lines? It begs the question of why the Leafs should trade away one of their core forwards. This might be why Leafs management has failed to pull off a trade of this magnitude because the downside of trading away a star player can be disastrous. You could end up with an Isaiah Thomas situation which is not what you want.
Jonathan Huberdeau and Matthew Tkachuk Flip-Flop in 2022
Florida receives: Matthew Tkachuk and a conditional fourth-round pick in 2024
Calgary receives: Jonathan Huberdeau, MacKenzie Weegar, Cole Schwindt and a conditional first-round pick in 2025
While there were other pieces to this trade this was more of a true one-for-one trade. Tkachuk for Huberdeau. At the time of the trade, these two stars were comparable. Both of them came off their first 100-point seasons. One achieved this through skill and unbelievable playmaking abilities – Jonathan Huberdeau and Tkachuk relied upon agitation, hard work and gritty play.
At the time of the trade, it was widely believed that Calgary had won. Fans and observers alike always place a high value on skill because it’s fun to watch and while Tkachuk’s ability to get under the skin of opposing players is quite entertaining, skill is king, and Huberdeau had far-reaching playmaking abilities which Tkachuk did not possess.
GM’s alike probably viewed Tkachuk as the better of the two probably due to his age and the fact that his best playing days were ahead of him while Huberdeau was in his prime and had peaked already.
Whichever way you looked at it, maybe you favoured Tkachuk or Huberdeau, they were comparable to each other. If you ignored these two and looked at the other pieces, Calgary won this trade by a landslide. They received a top defensive defenseman in MacKenzie Weegar which is hard to come by, a mid-level prospect in Cole Schwindt and a conditional first-round pick. The Panthers received a conditional fourth-round pick.
Two years later however and it’s clear that the Florida Panthers won this trade. In the two years since they’ve made it to the Stanley Cup Finals twice, losing in the first year and being victorious the other. Tkachuk has put up a total of 197 regular season points. The Calgary Flames on the other hand have entered into a rebuild and Huberdeau has struggled to regain his Florida form. He has only totalled 107 points since arriving in Canada.
A star for a star, similar to the Leonard and DeRozan trade, the Leafs could potentially be seeking something similar to this one. Hockey is a weird game. I don’t think most people would’ve guessed that Huberdeau’s play would drop off the way it did, but this was a good trade for both sides at the time. Both teams were in win-now mode. Florida was on the up-and-up and they made a splash to pull them over the top and they were right. Calgary had a bit of a different mindset, star forwards Tkachuk and Johnny Gaudreau told management they didn’t want to re-sign and instead of selling for futures they wanted to stay competitive and the return they got with their backs against the wall is most impressive.
Trading away Mitch Marner isn’t difficult to do. However, pulling off a trade that makes the Maple Leafs better today is the problem and he must go to a team that can first afford him and second, they must also be in win-now mode, this is the difficult part. Let’s compile a list of a few teams that would be game for Mitch Marner.
| Target Teams | Possible Teams | Non-target Teams |
|---|---|---|
| – Winnipeg Jets – Boston Bruins – Buffalo Sabres – NY Islanders – Philadelphia Flyers – Dallas Stars – Los Angeles Kings | – Detroit Red Wings – Ottawa Senators – NY Rangers – Carolina Hurricanes – Washington Capitals – Pittsburgh Penguins – New Jersey Devils – Nashville Predators – St. Louis Blues – Minnesota Wild – Utah Hockey Club – Vancouver Canucks – Vegas Golden Knights – Seattle Kraken | – Florida Panthers – Tampa Bay Lightning – Montreal Canadiens – Columbus Blue Jackets – Colorado Avalanche – Chicago Blackhawks – Edmonton Oilers – Calgary Flames – San Jose Sharks – Anaheim Ducks |
The majority of teams in the target list are win-now teams but similar to the Leafs they have had a limited amount of success in the post-season and require a change. They’re also teams that I think will benefit greatly from an elite goal scorer.
The possible teams category are similar to the target ones. They’re teams in win-now mode currently like the Rangers, Golden Knights and Hurricanes. Or they’re teams on the come-up, at the end of the rebuild stage and looking to be a contender for years to come like the Red Wings and Senators.
The non-target teams can range from win-now teams who don’t require the services of a Mitch Marner because they’re already top-heavy such as the Florida Panthers, Edmonton Oilers and Tampa Bay Lightning and then you’ve got the teams who are in the midst of a rebuild such as the San Jose Sharks and Anaheim Ducks.
In reality, this is a tough list to compile because all teams in a contending window will make a call on Mitch Marner because he is a young and elite-scoring forward which all GMs want and something that a team can never have enough of. Moving forward, we will rule out all non-target teams for possible trade scenarios with Toronto.
As I stated in Part 2, Joseph Woll is the future of Toronto Maple Leafs goaltending, so if the Maple Leafs are trying to upgrade here, the tendy they get in return must be an absolute star in the NHL today and continue to be one for at least the next few years.
| Toronto Receives | Dallas Receives |
|---|---|
| – Jake Oettinger – Logan Stankoven – 2026 2nd round draft pick | – Mitch Marner – Joseph Woll |
This trade would shock the hockey world. Jake Oettinger is only 25 and has 3 years of full-time NHL duties already under his belt. He has a career save percentage of .913 and a GAA of 2.51 which are superstar goaltender type numbers. Jake’s playing like a Vezina-calibre goalie and at only 25 years of age we haven’t even seen his best, he’s still developing.
To get Jake, the Leafs would have to trade Mitch Marner and since a goalie of Jake’s stature only requires a formidable backup, Joseph Woll is no longer needed. In return, the Leafs need to replace Marner’s goal-scoring and I don’t think there’s a better fit than the 21-year-old, Logan Stankoven. Logan was the 47th overall pick by the Dallas Stars in the 2021 NHL draft and the sky is the limit for this young forward. The CHL Player of the Year in 2022 has put up impressive numbers in major junior and the AHL. The Dallas Stars gave him a look late last season and he did not disappoint, he posted 6 goals and 14 points in 24 NHL games. Logan is NHL-ready and is a potential superstar in the game today. To butter things up for the Leafs, we will also receive Dallas’s 2nd round draft pick in the 2026 NHL Entry Draft.
This trade makes sense on both sides, Dallas is extremely well-rounded, they boast a strong offence, a good defence and excellent goaltending. By making this trade their offense becomes elite and their goaltending remains strong. Joseph Woll and Casey DeSmith form a formidable duo. They also have the salary cap space to pull this off. Cap Friendly projects the Dallas Stars have about $7.1 million in cap space right now, Jake Oettinger carries a cap hit of $4 million for one more year and Logan is signed for the next two years at $894,167. Totalling around $12 million in cap space. Marner and Woll combined have a cap hit of about $12 million for next year so this equals each other out Dallas has been a perennial Stanley Cup threat for the past few years but they’ve been unable to achieve hockey’s ultimate goal. A shakeup might be exactly what they need.
Toronto also comes away as a winner because goaltending becomes a non-issue and they now have cap space to work with, so they can add elsewhere if needed. The second-round draft pick allows the Leafs to re-stock their depleted prospect profile or gives them an additional trade chip moving forward.
Other Goaltenders the Leafs Could Target
Thatcher Demko, Jordan Binnington, Juuse Saros, Jacob Markstrom, Tristan Jarry, Igor Shesterkin, Ilya Sorokin, Connor Hellebuyck and Jeremy Swayman.
| Toronto Receives | Buffalo Sabres Receives |
|---|---|
| – Owen Power | – Mitch Marner |
I’m not sure how both teams would feel about making a trade with a division rival, but if the Leafs want to acquire a number 1 defenseman, this is exactly how they would do it.
Owen Power checks off so many boxes for the Leafs. He’s tall at 6’6”, and big at about 217 lbs, but unlike most big men in the NHL today, skating is one of his strong suits. Mr. Power is also young. The Maple Leafs most prized defensive possession right now is Morgan Rielly and he is already 30 years old which isn’t something you want to hear as a Leafs fan. The 21-year-old has registered 71 points in 163 career games and 14 of those have come from the power play. He also ranked fourth on the Buffalo Sabres for time on ice on the PK, so he has and can play on both sides of the ice in the NHL. With the 2023 NHL Calder Trophy Finalist in the fold, the Maple Leafs now boast a big three on defence. Morgan Rielly, Jake McCabe and Owen Power.
Buffalo has been in a rebuild for so long now and it finally seems like they’re going to break out of it. Even without Owen Power, their defence is strong and young. Rasmus Dahlin leads the charge along with defenders Mattias Samuelsson, Bowen Byram and Henri Jokiharju who are all younger than 26 years old. The future of their goaltending is bright with Devon Levi and Ukko-Pekka Luukkonen leading the way and their forward group is surrounded with good young players such as Tage Thompson, JJ Peterka and Dylan Cozens. By adding Mitch Marner to that group their offence becomes a force with room to grow.
| Toronto Receives | New Jersey Devils Receives |
|---|---|
| – Dougie Hamilton – Jonas Siegenthaler – Dawson Mercer – 2025 5th round draft pick | – Mitch Marner – Oliver Ekman-Larsson – 2026 3rd round draft pick |
If the Leafs wanted to make a move outside of their division but still within their conference, the New Jersey Devils are the perfect choice.
As good as Dougie Hamilton is and although the Devils will miss him, he is expendable. The Devils are stacked on defence at the moment. Young studs Luke Hughes and Simon Nemec will lead the group offensively while Brett Pesce and Brenden Dillon will be the defensive anchors on the backend.
Dougie Hamilton boasts a unique skill set. He’s offensively gifted and will become the new PP Quarterback of the Leafs. He’s also a stud come 5-on-5 play and is an excellent puck mover. Jonas Siegenthaler is 27 years old. He’s got 4 years left on his contract at $3.4 million which is very reasonable. Unlike Mr. Hamilton Jonas is known more for his defensive attributes and can certainly slot in on the penalty kill.
Dawson Mercer will partially replace the goal-scoring left by the departure of Mitch Marner. He came off a disappointing 2023-24 campaign which saw him score 20 goals and 33 points but he is only 22 years old, so there’s room to grow. The 2020 1st round draft pick could be a top-line talent in the league for years to come.
The Devils on the other hand will add superstar forward Mitch Marner to the fold. Oliver-Ekman Larsson will replace the puck-moving absence of Dougie Hamilton and they’ll receive Toronto’s 3rd round draft pick in the 2026 NHL Entry Draft.
Other Defensemen the Leafs Could Target
Hampus Lindholm, Alexander Romanov, Ryan Pulock, Travis Sanheim, Cam York, Miro Heiskanen, Thomas Harley, Jakob Chychrun, Jake Sanderson, Adam Fox, Jacob Trouba, Alex Pietrangelo, Noah Hanifin, Filip Hronek, Brock Faber, Jonas Brodin, Colton Parayko, Mikhail Sergachev and Jaccob Slavin.
This 3 Part Series (Part 1 and Part 2) dived into the Toronto Maple Leafs. We gave a review of their past playoff performances over the past 8 years. We looked at what was wrong with them and what was right. We theorized ways the Leafs could improve and what change looked like. How exactly could the Leafs get better with what they have and what was available to them? Finally, we worked through actual scenarios of what changing the Leafs looks like today.
Whether Brad Treliving and Maple Leafs upper management see this post or not, the current structure of the Toronto Maple Leafs isn’t working and change is needed for them to win hockey’s most prized possession. The Stanley Cup.
References
