I love trades, and I love rankings, and I’m a Toronto Maple Leafs fan, so it goes without saying that I love misery. For this post, I figured I’d combine all of those things into one piece, with a ranking of all the times the Maple Leafs have traded away a first-round pick. After all, it feels like a timely topic right about now.
After some digging, I found there have been 29 separate trades in Leafs history in which they’ve traded away a total of 31 first-round picks, so I did what any normal person would do and ranked them all, from the ones that turned out best to worst.
Two things surprised me about that. First, 29 seems low. The Leafs seem to do this kind of thing a lot. I was pretty sure Brad Treliving had traded away 29 firsts on his own, although I guess the math doesn’t quite work out on that one. Give him time, guys, he’s working on it.
The second surprise was the best-to-worst part, since that implies that some of these trades have worked out in the Leafs’ favor. I didn’t think they’d all be disasters, mind you, because some of these are going to be boring draft floor swaps that nobody even remembers. Finding actual wins, though? Impossible. Or so I thought.
We’re doing this with the total benefit of hindsight, which isn’t fair to the general managers, but too bad for them. Let’s go on this journey together.
The big wins29. Clark for Sundin
The trade: On the draft floor in 1994, the Leafs and Quebec Nordiques shocked the hockey world with a blockbuster. Toronto sent Wendel Clark, Sylvain Lefebvre, Landon Wilson and the 22nd pick to Quebec for Mats Sundin, Garth Butcher, Todd Warriner and the 10th pick.
The GM: Cliff Fletcher
The pick became: Jeff Kealty, who never played in the NHL
The verdict: The deal broke my heart at the time, but it stands as arguably the best trade in Leafs history. Clark and Sundin were such big names that the firsts were basically afterthoughts, but they were in the deal. It has to rank here.
Bonus fun fact: Kealty is now the Nashville Predators’ assistant GM and director of scouting.
28. The California goalie trade (that worked out)
The trade: At the 2016 draft, the Leafs sent the first (30th) and a future second to the Anaheim Ducks for Freddie Anderssen.
The GM: Lou Lamoriello
The pick became: Sam Steel, who’s still in the league but has never scored more than 10 goals
The verdict: A big win for Lamoriello, who found the (mostly) stable goaltending his young team would need for its early push to the playoffs.
27. The original
The trade: After making it through the first nine drafts without trading away a first, the Leafs went for it for the first time Jan. 31, 1971, sending their first, along with Bruce Gamble and Mike Walton, to the Philadelphia Flyers for Bernie Parent and a second.
The GM: Jim Gregory
The pick became: Pierre Plante, a winger who played nine NHL seasons and peaked with 66 points for the St. Louis Blues in 1974
The verdict: Plante was good, but Parent was a future Hall of Famer entering his prime. He wouldn’t last long in Toronto before it sent him back to the Flyers, but the Leafs got another first back in that deal. As a bonus, the second pick the Leafs got in the original Parent trade turned into Rick Kehoe, who was better than Plante.
Bernie Parent won the Vezina Trophy and Conn Smythe Trophy while with the Flyers in the 1973 and 1974 seasons. (Bruce Bennett / Getty Images)
You’d do it again26. Jake McCabe
The trade: Near the 2023 deadline, the Leafs sent a 2025 first, along with a second, Joey Anderson and Pavel Gogolev, to the Chicago Blackhawks for Jake McCabe, two fifths and Sam Lafferty.
The GM: Kyle Dubas
The pick became: Vaclav Nestrašil, a big winger who projects as a depth NHLer
The verdict: The Hawks also ate a bunch of salary here, and McCabe has been an important player in Toronto.
25. Brian Leetch
The trade: At the 2004 deadline, the Leafs sent a first, a second and two prospects to the New York Rangers for Brian Leetch.
The GM: John Ferguson Jr.
The pick became: Kris Chucko, taken with the 24th pick, who played two NHL games
The verdict: It was a lot to give up, especially given the lockout meant Leetch got only part of one season in Toronto. Still, Leetch ruled, and none of the picks or prospects amounted to much. This was a rare JFJ win.
24. Jake Muzzin
The trade: On Jan. 28, 2019, the Leafs sent their first, Sean Durzi and Carl Grundström, to the Los Angeles Kings for Jake Muzzin.
The GM: Kyle Dubas
The pick became: The pick ended up being No. 22, and the Kings took Tobias Bjornfot
The verdict: It wasn’t cheap, but Muzzin was a good addition, and the Leafs would probably make this deal again.
23. A swap of top-10 picks
The trade: On the 1998 draft floor, the Leafs traded down from the eighth pick to 10th. The Leafs also gave up a fourth, and got back a third and fifth.
The GM: Ken Dryden
The pick became: The Hawks took Mark Bell at eight, and the Leafs used the 10th pick on Nik Antropov
The verdict: None of the other picks turned into much, and Antropov was better than Bell, so call it a win.
22. Dmitri Yushkevich
The trade: In August 1995, the Leafs sent their 1996 first, plus a second and fourth, to the Flyers for 23-year-old defenseman Dmitri Yushkevich and a second.
The GM: Cliff Fletcher
The pick became: Dainius Zubrus
The verdict: Zubrus played nearly 20 years in the NHL but didn’t last long in Philadelphia and topped out as a 20-goal guy. Meanwhile, Yushkevich was an underrated stud who’d be a key part of the Pat Quinn-era turnaround. This deal was criticized at the time, but in hindsight, it was a win.
21. The Schenn Shuffle
The trade: At the 2008 draft, the Leafs traded the seventh pick plus a second and a third to the New York Islanders. Doing so moved Toronto up two spots to fifth, and it took Luke Schenn.
The GM: Cliff Fletcher 2.0, the interim version
The pick became: The Islanders flipped the pick again, this time to the Nashville Predators, who took Colin Wilson
The verdict: It felt like an overpay at the time just to move up two spots and take a defensive defenseman, and for years, fans would point at this as proof Fletcher had lost his fastball. In hindsight, though, the Leafs kind of did fine here. Schenn was good for a few years, then turned into James van Reimsdyk. Meanwhile, Wilson was a bust, and the second and third didn’t turn into much.
Bonus fun fact: The Islanders used the pick they got from the Predators on Josh Bailey, so they’re not asking for any do-overs, either.
20. The classic trade down
The trade: At the 2018 draft, the Leafs traded down from 25 to 29, picking up a third.
The GM: Kyle Dubas
The pick became: Dominik Bokk
The verdict: Bokk has yet to play in the NHL, and the Leafs wound up with Rasmus Sandin, whom they’d eventually trade for another first. Trading down works! (Sometimes. We’ll get to that.)
The Leafs originally signed Petr Mrazek to a three-year, $11.4 million contract in 2021 but lost him for the season to a groin injury. (Claus Andersen / Getty Images)
19. Take our goalie, please
The trade: At the 2022 draft, the Leafs gave the Hawks their first (No. 25) in exchange for a second, with Chicago taking on Petr Mrazek’s contract.
The GM: Kyle Dubas
The pick became: Sam Rinzel
The verdict: Rinzel’s a good rookie, the Leafs got Fraser Minten with the second, and Mrazek was better in Chicago than Toronto. Honestly, this one kind of worked out for everyone.
The break-evens18. The other 1994 draft floor deal
The trade: Moments after the Clark/Sundin blockbuster, the Leafs traded back down from the 10th pick, sending it to the Washington Capitals with Rob Pearson for Mike Ridley and the 16th.
The GM: Cliff Fletcher
The pick became: Nolan Baumgartner
The verdict: The Leafs used their pick on Eric Fichaud, and neither he nor Baumgartner did a lot in the NHL. Ridley was fine. Pearson was cool. Call it even.
Bonus fun fact: The Baumgartner pick ended up being part of this trade, the Clark/Sundin deal and the original Eric Lindros trade.
17. Wayne Thomas
The trade: During the 1975 offseason, the Leafs traded their 1976 first to the Montreal Canadiens for goalie Wayne Thomas.
The GM: Jim Gregory
The pick became: Peter Lee, who never played for Montreal but had two 30-goal seasons for the Pittsburgh Penguins
The verdict: Thomas played in the All-Star Game in his first year in Toronto but was lost on waivers two years later.
16. Ryan O’Reilly
The trade: At the 2023 deadline, the Leafs sent a first to the Blues as part of a three-way trade that landed them Ryan O’Reilly.
The GM: Kyle Dubas
The pick became: Otto Stenberg
The verdict: Stenberg is still a decent prospect. O’Reilly at least helped the Leafs win a playoff round before bolting. For now, this one is OK.
The shrugs and to-be-determineds15. The most boring trade on this list
The trade: At the 2024 draft, the Leafs traded down with Anaheim, moving from 23rd to 31st and picking up a second.
The GM: Brad Treliving
The pick became: Stian Solberg
The verdict: Solberg is still in the Ducks system and probably projects as a better defenseman than Ben Danford, who wound up with the Leafs. Mix in the second, and we can call it roughly even for now.
14. Scott Laughton
The trade: At the 2025 deadline, the Leafs sent Nikita Grebenkin, two late-round picks and their 2027 first to Philadelphia for Scott Laughton.
The GM: Brad Treliving
The pick became: TBD (and top 10 protected)
The verdict: Hard to say until we see where and whom the pick turns into, but it’s not looking great right now.
13. Brandon Carlo
The trade: At the 2025 deadline, the Leafs sent Fraser Minten, a fourth and their 2026 first to the Boston Bruins for Brandon Carlo.
The GM: Brad Treliving
The pick became: TBD, although we should point out that it’s top five protected. (Checks standings.) Yeah, it’s definitely going to be sixth.
The verdict: I guess we have to wait and see, although given how Carlo has looked in Toronto and Minten has looked in Boston, along with the Leafs’ season in general, it’s not trending great for Toronto.
The regrets12. Nick Foligno
The trade: At the 2021 deadline, the Leafs sent their first and a fourth to the Columbus Blue Jackets for Foligno. They also gave a fourth to the San Jose Sharks for cap retention.
The GM: Kyle Dubas
The pick became: Corson Ceulemans
The verdict: Foligno didn’t do much, and the Leafs flamed out against the Habs. Ceulemans is still in the Columbus system but hasn’t made the NHL, which lessens the sting a bit.
11. The two-fer
The trade: For the first time in their history, the Leafs traded two firsts in the same deal March 13, 1978. The deal saw them send their first in 1978 and 1980 to the Detroit Red Wings, along with Errol Thompson and a second, in exchange for Dan Maloney and a second.
The GM: Jim Gregory
The picks became: Brent Peterson at No. 12 in 1978 and Mike Blaisdell at No. 11 in 1980. Both guys played in the NHL until 1989, but neither was more than a depth player.
The verdict: This one’s a loss because Thompson was more productive than Maloney, but the picks didn’t hurt that much.
Bonus fun fact: A few years after he retired, Maloney became the Leafs’ coach at the age of 34. He lasted two years, including a last-place finish in 1985, but that got them Wendel Clark, so thank you, Dan.
10. A 1992 pick swap
The trade: At the 1992 draft, the Leafs traded down from the fifth pick, getting the eighth plus a second-rounder from the Islanders.
The GM: Cliff Fletcher
The pick became: Darius Kasparaitis
The verdict: We don’t know that the Leafs would have taken Kasparaitis, and in fact, there’s a good chance they might have grabbed Ryan Sittler, the son of Leafs legend Darryl, who ended up going seventh and never made the NHL. They wound up with Brandon Convery, so overall, it didn’t really work.
Bonus fun fact: The second pick in this trade was flipped to Washington, who took future Vezina winner Jim Carey.
9. Owen Nolan
The trade: At the 2003 deadline, the Leafs sent Alyn McCauley, Brad Boyes and their first to the Sharks for Owen Nolan. The pick ended up being No. 21.
The GM: Pat Quinn
The pick became: Mark Stuart
The verdict: Given how insanely loaded the 2003 draft was — Ryan Getzlaf and Brent Burns went with the two picks right before Stuart — this could have been a lot worse. It was still an overpay, since Nolan never quite fit in Toronto, but maybe not as bad as you might remember. Hey, we’ll always have “boo hoo.”
7 and 8. The perils of trading down
The trade: This is technically two trades, but we’ll combine them. On the floor of the 2015 draft, the Leafs sent their first (No. 24) to the Flyers for No. 29 and a second, then shortly after, sent No. 29 to Columbus for a second and third.
The GM: They were between GMs, but Dubas and Mark Hunter were in charge.
The pick became: The Flyers got Travis Konecny, and the Blue Jackets took Gabriel Carlsson.
The verdict: In theory, trading down 10 slots to acquire two extra picks makes sense. In reality, missing out on Konecny was a disaster, especially given the best the Leafs did on those extra picks was Travis Dermott.
6. Thank you, Kessel
The trade: On the eve of the 2009 season, the Leafs traded their 2010 and 2011 firsts to the Bruins for the rights to Phil Kessel.
The GM: Brian Burke
The picks became: Tyler Seguin, the No. 2 pick in 2010, and then Dougie Hamilton, the ninth pick in 2011.
The verdict: Kessel was a beauty, but this was way too much to give up, given how far away that Leafs team was. Burke was a maestro when it came to trading, especially in Toronto, but he badly misjudged his own team in making this deal.
The disasters5. The California goalie trade (that did not work out)
The trade: At the 2007 draft, the Leafs sent their first (13th), a second and a fourth to San Jose for Vesa Toskala.
The GM: John Ferguson Jr.
The pick became: Lars Eller
The verdict: Dude.
Vesa Toskala repaid the Leafs for sacrificing a first-round pick by allowing one of the worst goals imaginable in 2008. (Geoff Burke / Imagn Images)
4. The other Clark trade
The trade: At the 1996 deadline, the Leafs traded their 1997 first to the Islanders along with Kenny Jönsson, Sean Haggerty and Darby Hendrickson in exchange for Wendel Clark and Mathieu Schneider.
The GM: Cliff Fletcher
The pick became: The fourth pick, which the Islanders used on Roberto Luongo.
The verdict: I’ll go to my grave saying this trade wasn’t as bad as it’s made out to be, because Clark scored 30 goals for the Leafs, Schneider was good (and turned into Bryan McCabe), they wouldn’t have taken Luongo anyway with Felix Potvin still around, and we at least got this moment out of it. Still, “not as bad as you think” doesn’t translate to “good,” especially when you spend the next few decades watching Luongo forge a Hall of Fame career.
Bonus fun fact: This is the trade that spawned Fletcher’s infamous “draft schmaft” sound bite.
3. A Biggs mistake
The trade: On the 2011 draft floor, the Leafs traded the last pick of the first round and their own second to the Ducks to move up to 22 and take Tyler Biggs.
The GM: Brian Burke
The pick became: The Ducks used the 30th pick on Rickard Rakell.
The verdict: Biggs never played a shift in the NHL, so giving up the Rakell pick is bad enough. It gets worse, though, because that early second-rounder turned into John Gibson.
2. No Country Draft Pick for Old Men
The trade: At the 2020 draft, the Leafs sent their first (No. 13) to the Carolina Hurricanes to dump the last year of Patrick Marleau’s contract.
The GM: Kyle Dubas
The pick became: Seth Jarvis
The verdict: Horrific, although most of that blame falls on the original Marleau UFA signing, which was a Lamoriello move. Still, this was a massive price to unload one season of cap headache.
And finally, the one you all knew was coming in this spot …
1. Tom Kurvers
The trade: On Oct. 16, 1989, the Leafs traded their first-round pick for the first time in over a decade. Specifically, it was the first from the 1991 draft, and it went to the New Jersey Devils for defenseman Tom Kurvers.
The GM: Floyd Smith
The pick became: (sigh) Scott Niedermayer
The verdict: This is the single worst trade in Toronto Maple Leafs history, and maybe not even for the reason you think. Missing out on Niedermayer was more than bad enough, but the reality is this trade probably cost the Leafs the first pick, which is to say Eric Lindros. Once it was clear the 1990 Leafs would be terrible, they went on a spending spree to acquire veteran talent to keep them out of last, which only made their future outlook worse.
The Nordiques ended up eking out the Lindros “race,” and we all know how that all turned out. If it had been the Leafs, a huge chunk of modern NHL history changes. As it stands, the Leafs got a decent defenseman for a few seasons, and missed out on the chance at a legitimate franchise player they desperately needed.