Toronto Maple Leafs Trade Deadline History - The Hockey Writers - Maple Leafs History

*This archive was originally published before the 2022 trade deadline

At the 2022 NHL Trade Deadline, the Toronto Maple Leafs were right in the middle of all the drama. They had been linked to just about everybody, including forwards, defensemen, and goaltenders. Prior to the deadline passing, former THW writer Alex Hobson took a look at the Maple Leafs trade deadline history.

Wendel Clark Toronto Maple Leafs Rick Wamsley St. Louis Blues — Wendel Clark, Toronto Maple Leafs and Rick Wamsley, St. Louis Blues, April 1986. (Photo by Graig Abel)

In this piece, Alex recapped what he believed to be the Maple Leafs’ five best and five worst trade deadline moves in their history. These deals all happened within a month of the trade deadline, so they’re not limited to solely trades that happened on deadline day.

Top 5 Best Trades

Maple Leafs Trade Jamie Macoun to Detroit

Truthfully, there isn’t really anything about this trade that will make your jaw drop. But if you’re a seller at the trade deadline and you turn a veteran into a draft pick and then turn that draft pick into a serviceable NHL player, it should be seen as a win.

The Maple Leafs acquired Jamie Macoun in Jan. 1992 as part of a package that brought Doug Gilmour to Toronto. He was a serviceable defenseman for them for six and a half seasons, but with the Maple Leafs on track to miss the playoffs for the second straight time in 1997-98, they traded Macoun to the Detroit Red Wings in exchange for a fourth-round pick.

The trade worked out for everyone in the end. Macoun won a Stanley Cup with the Red Wings that year, and the Maple Leafs used that fourth-round pick to select Alexei Ponikarovsky. The Ukrainian forward scored at least 20 goals in three of his six full seasons with the Maple Leafs, which was more than what they’ve been able to say for some other trades.

Maple Leafs Get a Haul For Kaberle and Versteeg

I’m going to cheat a little bit here and include two trades because they were made within days of each other and garnered similar returns. On Feb. 14, 2011, the Maple Leafs traded forward Kris Versteeg to the Philadelphia Flyers in exchange for a first-round pick and a third-round pick. Four days later, they traded longtime defenseman Tomas Kaberle to the Boston Bruins for a first-round pick, 2008 first-round pick Joe Colborne, and a second-round pick.

The Maple Leafs didn’t have their own first-round pick in 2011, having dealt it to the Bruins ahead of the 2009-10 season, so this trade deadline looked like a massive success at the time. Of course, the regime at the time fumbled the ball in every possible way with those draft picks.

Tomas Kaberle, seen here with the Boston Bruins (Icon SMI)

They used Philadelphia’s first-round pick to select defenseman Stuart Percy, who only has 12 NHL games to his name, and ended up using Boston’s first-round pick and their own second-round pick to trade up in the first round. They used that pick, at 22nd overall, to select forward Tyler Biggs, who never suited up for an NHL game let alone for the Leafs and is widely regarded as one of the franchise’s biggest draft busts. The lack of success from their selections sort of makes these deals redundant, but the work done in the trades themselves was very good.

Domi Comes Back to Toronto

Ask any Maple Leafs fan who watched the team in the late 1990s and early 2000s, and odds are most of them will have fond memories of Tie Domi, one of the best enforcers to ever play the game. The Maple Leafs drafted Domi in 1988, traded him to the New York Rangers in 1990, and then re-acquired him, this time from the Winnipeg Jets, in exchange for Mike Eastwood in 1995.

Eastwood never ended up being more than a journeyman player in the NHL, whereas Domi established himself as one of the most feared enforcers in the league. He set a Maple Leafs’ single-season record for most penalty minutes with 367, and his tenure in Toronto was sprinkled with controversy and incidents including a sucker punch to the face of New York Rangers defenseman Ulf Samuelsson in 1994-95, and a penalty box fight with a fan in 2000-01.

Domi remains the NHL’s all-time leader in fights with 333, and although his offensive contributions to the Maple Leafs were few and far between, he gave Maple Leafs’ faithful something to cheer for during what many would say were the last glory days the team has had to date.

Maple Leafs Shed Clarkson’s Contract

After the Maple Leafs made the playoffs during the lockout-shortened 2012-13 season, then-general manager Dave Nonis was feeling encouraged and made a couple of moves prior to the season. He traded for Stanley Cup-winner Dave Bolland and signed New Jersey Devils power forward David Clarkson to a seven-year contract worth an average annual value (AAV) of $5.25 million.

Maple Leafs Acquire Leetch for One Last Push

Brian Leetch was one of the NHL’s best offensive defensemen throughout his career, managing 50 points in 11 of his 17 NHL seasons. Having spent the majority of it with the New York Rangers, the Maple Leafs swung a deal to acquire Leetch in 2003-04, sending prospects Maxim Kondratiev and Jarkko Immonen along with a first-round pick, who ended up being Kris Chucko, the other way.

None of the players the Maple Leafs gave up in this deal ended up carving out an NHL career. Meanwhile, Leetch had 15 points in 15 games during the rest of the season and added eight points in 13 playoff games to go with it. The Maple Leafs didn’t get the Stanley Cup run they were hoping for, but Leetch was a key contributor for them and had one year left on his contract. Or, at least he should have.

Brian Leetch New York Rangers — Brian Leetch, New York Rangers (Wikipedia)

The 2004-05 lockout wiped out all NHL games that season, and thus, the last year of Leetch’s contract was a wash. He became an unrestricted free agent ahead of the 2005-06 season and signed a contract with the Bruins before retiring following that season. Then general manager John Ferguson Jr made some atrocious trades during his tenure with the Maple Leafs, but credit where credit’s due, this was one of the good ones. And who knows what Leetch and the Maple Leafs may have been able to accomplish had there been a 2004-05 season.

Top 5 Worst Trades

Leafs Trade a Haul For Owen Nolan

After making at least the second round in the previous four seasons, the Maple Leafs felt confident enough to pull the trigger on a trade for Owen Nolan at the 2003 Trade Deadline. He was a proven 20-goal scorer who was coming off a 66-point season with the San Jose Sharks the year before. Back the other way went forward Alyn McCauley, 2002 first-round pick Brad Boyes, and a first-round pick in 2003.

The trade initially looked great. Nolan scored seven goals and added 12 points in 14 games to close out the 2002-03 season, but turned into a complete ghost in the playoffs. The Philadelphia Flyers eliminated the Maple Leafs in the first round, and Nolan only managed two assists in the seven-game series. The following season, he kept up his offensive production with 48 points in 65 games but suffered a late-season injury and missed the entirety of the playoffs. The lockout happened the year after, and he ended up signing with the Phoenix Coyotes for the 2006-07 season.

Meanwhile, McCauley put up 47 points of his own in 2003-04, Boyes went on to score 43 goals in 2007-08 and 33 goals the season after, and the 2003 first-round pick ended up being defenseman Mark Stuart, a player who most certainly could have helped the Maple Leafs’ back end throughout the mid-2000s.

Maple Leafs Acquire a Notorious Scapegoat

Sitting seventh place in the Eastern Conference with their sights set on a playoff run in 2000-01, the Maple Leafs wanted to add some size to their back end. The result ended up being the acquisition of Aki Berg from the Los Angeles Kings in exchange for forward Adam Mair and a second-round pick.

Berg, who stood at 6-foot-3 and 216 pounds, couldn’t use his size to save him from the wrath of Maple Leafs fans, however. He ended up becoming the team’s scapegoat, and his addition didn’t really add much to a back end that already employed the likes of Kaberle, Bryan McCabe, Danny Markov, and Dmitri Yushkevich. Especially when you consider that the Maple Leafs only scored more than three goals once during that playoff run, maybe they should have gone after some offense instead of a big body.

While Mair was a serviceable bottom-six player for the following nine seasons of his career, the real stinger here is that the second-round pick turned into forward Mike Cammalleri. Essentially, the Maple Leafs traded a forward who was usually good for 20 goals and 50 points in exchange for a guy who Leafs fans LOVED to hate. Probably not the move to make in hindsight.

Leafs Acquire Foligno for Their Fifth-Straight Early Exit

Most of the deals I’ve listed so far happened in an entirely different era, which makes talking about them a little bit easier. For this one, however, the wound is still fresh. Sitting first place in the one-off North Division in 2020-21, the Maple Leafs traded a first-round pick and two fourth-round picks to acquire forward Nick Foligno from the Columbus Blue Jackets in a three-way deal that involved the San Jose Sharks as a neutral broker for salary retention. Foligno was the captain of the Blue Jackets at the time and helped manhandle the Maple Leafs in the 2019-20 playoff bubble play-in series.

With the below-.500 Montreal Canadiens waiting for them in a first-round matchup, the acquisition of Foligno should have given them a veteran middle-six forward who could chip in offensively and shut down opposing forwards. Basically, the logic here was that if the Maple Leafs could capitalize on their odds of making a deep playoff run, giving up a first-round pick would be worth it.

Nick Foligno Morgan Rielly Mitchell Marner Toronto Maple Leafs — Nick Foligno, Morgan Rielly and Mitch Marner, Toronto Maple Leafs (Photo by Darcy Finley/NHLI via Getty Images)

However, Foligno’s short time as a Maple Leaf was riddled with injuries. He played a combined eleven games for the team and only managed five assists. I even wrote an article after the season was done about why I thought they should re-sign him and finish what they started. But, in hindsight, it’s a good thing they didn’t listen to me because Foligno has clearly lost a step and only had 13 points in 64 games for the Bruins in 2021-22. Foligno was far from the reason the Maple Leafs lost in the first round, but this trade definitely added another element of skepticism when it comes to trading first-round picks for rentals.

Clark Returns to Toronto

Remember what I said about Domi’s affection to Leafs fans earlier? Throw Clark into that same boat. The Maple Leafs traded Clark to the Quebec Nordiques in a blockbuster following the 1993-94 season that brought Mats Sundin to the Maple Leafs, and only two years later, they re-acquired Clark in a separate blockbuster, this time with the New York Islanders.

The full trade saw the Maple Leafs acquire Clark, Mathieu Schneider, and D.J. Smith from the Islanders in exchange for Darby Hendrickson, Sean Haggerty, Kenny Jonsson, and a first-round pick in 1997. Leafs fans were ecstatic with the thought of having Clark back on the team, this time alongside Sundin and Gilmour as well, and the trade looked great to start. Clark immediately put up 15 points in 13 games for the Maple Leafs, but they went on to lose in the first round to the St. Louis Blues.

Roberto Luongo, Timo Meier — Former Florida Panthers Goaltender Roberto Luongo blocks a shot from San Jose Sharks Timo Meier. (AP Photo/Brynn Anderson)

Clark scored 30 goals the following season for Toronto, but they missed the playoffs that year and the next, and Clark signed with the Tampa Bay Lightning prior to the 1998-99 season. Jonsson went on to be a rock on the Islanders’ back end, but the worst part of that trade is what ended up happening with that first-round pick. The Maple Leafs had a disastrous, injury-riddled season in 1996-97, and the Islanders used that pick to select goaltender Roberto Luongo at fourth overall.

For a Maple Leafs team that employed *checks notes*, Andrew Raycroft, Vesa Toskala, Jonas Gustavsson among others through the mid-to-late 2000s and early 2010s, they certainly could have used Luongo’s presence between the pipes. Maybe bringing back Clark wasn’t worth it, but the fans were emotionally on board with it at the time.

Maple Leafs Trade a Future Norris Winner

The problem with trades like these is that draft picks are always voodoo. We’ve seen first-overall picks immediately flop, and we’ve seen seventh-round picks turn into Hall-of-Famers. With the Maple Leafs on the outside looking into a bad Eastern Conference playoff picture in 2006-07, they swung a deal to acquire veteran faceoff specialist Yanic Perreault from the Phoenix Coyotes in exchange for defenseman Brendan Bell and a second-round pick in 2008.

The Maple Leafs’ playoff hopes quite literally came down to the last game of the season that year, and it wasn’t even in their hands. But an Islanders shootout victory over the New Jersey Devils gave them the edge over the Maple Leafs, and they missed the playoffs. Perreault did not re-sign with the team, inking a contract with the Chicago Blackhawks for the 2007-08 season and ended up retiring at the end of that season.

Roman Josi Nashville Predators — Roman Josi, Nashville Predators (Jess Starr/The Hockey Writers)

The loss of Bell on the back end didn’t hurt at all and never come back to bite them. But let’s revisit that second-round pick they traded. That pick ended up in the hands of the Nashville Predators, who used it to select defenseman Roman Josi. The Swiss defender is currently in his 13th season with the Predators and has established himself as one of the league’s top defensemen. He led all NHL defensemen in scoring in 2021-22 with 96 points in 80 games and won the James Norris Memorial Trophy in 2019-20 as the league’s best defenseman.

You can argue that the acquisition of Perreault was a necessary move to push the team into the playoffs that season, but his offense immediately dipped when he got to Toronto and they didn’t even get to enjoy his faceoff ability in the postseason. Meanwhile, the Maple Leafs got to watch Josi develop into a star on the Predators’ blue line while spending years of their own searching for stability on their own back end. If you didn’t already know the conditions of this trade, I’m sorry I had to be the one to break it to you.

Last 5 Deadlines Trade Tracker

2023-24

Feb. 29, 2024: Maple Leafs trade a 2025 third-round pick to the Anaheim Ducks for Ilya Lyubushkin

March 7, 2024: Maple Leafs trade a 2024 third-round pick and a 2025 fifth-round pick to the Washington Capitals for Joel Edmundson

Joel Edmundson Toronto Maple Leafs — Joel Edmundson, Toronto Maple Leafs (Amy Irvin / The Hockey Writers)

March 7, 2024: Maple Leafs trade a 2026 sixth-round pick to the Carolina Hurricanes for Cade Webber

March 8, 2024: Maple Leafs trade a 2026 fourth-round pick and Dmitiry Ovchinnikov to the Minnesota Wild for Connor Dewar

2022-23

Feb. 17, 2023: Maple Leafs trade Adam Gaudette, Mikhail Abramov, a 2023 first-round pick, a 2023 third-round pick, and a 2024 second-round pick to the St. Louis Blues for Ryan O’Reilly and Noel Acciari.;

Feb. 17, 2023: Maple Leafs trade a 2025 fourth-round pick to the Minnesota Wild for Josh Pillar.

Feb. 27, 2023: Maple Leafs trade Joey Anderson, Pavel Gogolev, a conditional 2025 first-round pick and a 2026 second-round pick to the Chicago Blackhawks for Jake McCabe, Sam Lafferty, a conditional 2024 fifth-round pick and a conditional 2025 fifth-round pick

Feb. 28, 2023: Maple Leafs trade Rasmus Sandin to the Washington Capitals for Erik Gustafsson and a 2023 first-round pick (Easton Cowan)

Feb. 28, 2023: Maple Leafs trade Pierre Engvall to the New York Islanders for a 2024 third-round pick

Feb 28, 2023: Maple Leafs trade a 2023 third-round pick to the Vancouver Canucks for Luke Schenn

March 3, 2023: Maple Leafs trade Dryden Hunt to the Calgary Flames for Radim Zohorna

2021-22

March 20, 2022: Maple Leafs trade second-round picks in 2022 and 2023 as well as a 2024 third-round pick to the Seattle Kraken for Mark Giordano and Colin Blackwell.

March 20, 2022: Maple Leafs trade Travis Dermott to the Vancouver Canucks for a 2022 third-round pick.

2020-21

April 11, 2021: Maple Leafs trade a 2021 first-round pick and a 2022 fourth-round pick to Columbus in exchange for Nick Foligno, and trade a 2021 fourth-round pick to San Jose in exchange for Stefan Noesen.

April 11, 2021: Maple Leafs acquire goaltender David Rittich from Calgary in exchange for a 2022 third-round pick.

April 11, 2021: Maple Leafs acquire defenseman Ben Hutton from Anaheim in exchange for a 2022 fifth-round pick.

April 11, 2021: Maple Leafs trade forward Alexander Barabanov to San Jose in exchange for forward Antti Suomela.

2019-20

Feb. 5, 2020: Maple Leafs acquire goaltender Jack Campbell and forward Kyle Clifford from Los Angeles in exchange for forward Trevor Moore, a third-round pick in 2020, and a conditional third-round pick in 2021.

Feb. 19, 2020: Maple Leafs acquire forward Denis Malgin from Florida in exchange for forward Mason Marchment.

Feb. 19, 2020: Maple Leafs acquire forward Max Veronneau from Ottawa in exchange for forward Aaron Luchuk and a conditional sixth-round pick in 2021.

Feb. 22, 2020: Maple Leafs acquire defenseman Calle Rosen from Colorado in exchange for goaltender Michael Hutchinson.

Feb. 22, 2020: Maple Leafs acquire forward Miikka Salomaki from Nashville in exchange for defenseman Ben Harpur.

Jan. 28, 2019: Maple Leafs acquire defenseman Jake Muzzin from Los Angeles in exchange for forward Carl Grundstrom, defenseman Sean Durzi, and a 2019 first-round pick.

Maple Leafs’ Deadline Moves Not Much to Brag About

My main takeaway from writing this piece is that, wow, it’s very seldom the Maple Leafs make a move at the trade deadline that actually works for them. There’s clearly a lot to be said about dangling draft picks for players who you’ll only be able to use for the rest of the season, although that’s a gamble you have to make sometimes.

I considered putting the Jake Muzzin trade on here as one of the best trades, but the Maple Leafs didn’t have any playoff success during his time with the Maple Leafs, and Grundstrom and Durzi have had successful NHL careers.

Treliving’s First Deadline as Maple Leafs’ GM

The 2024 NHL Trade Deadline was Brad Treliving’s first as the club’s GM and many considered it to be a good one after his moves in the offseason brought in grit with Max Domi, Tyler Bertuzzi and Ryan Reaves. At the deadline, he brought in more of the same with Lyubushkin and Edmundson who played the game hard.

Brad Treliving Toronto Maple Leafs — Brad Treliving, General Manager of the Toronto Maple Leafs (Amy Irvin / The Hockey Writers)

He also acquired Connor Dewar, who is a scrappy forward and goes into the dirty areas. He showed that he is an above-average penalty killer, which is exactly what the Maple Leafs needed help with. Treliving also traded for the rights of Webber from the Hurricanes, who fits the mould of what Treliving likes in a defenceman. He is a 6-foot-7, 200-pound blueliner, who hits, blocks shots, and breaks up the cycle very well. Overall, Treliving did well in his first deadline at the helm of the Maple Leafs, but his true test will come at his second deadline when he has Marner and Tavares’ futures looming over his head.