The consensus around the NHL is that general managers always overpay at the trade deadline. While that certainly can be true in some cases, sometimes what was seen as an overpayment, ends up being pennies on the dollar.
The 2024 NHL trade deadline is just over a week away and the Toronto Maple Leafs are expected to be adding some talent to the roster for what they hope is a long Stanley Cup Playoff run. GM Brad Treliving enters his first deadline day in Toronto and he’s never been one to be shy about making a bold transaction.
We’ve already uncovered some of the worst trade deadline deals, it’s time to showcase the best. Here are five of the best deals leading up to the trade deadline in recent Leafs’ history:
Tomas Kaberle to the Boston Bruins for Joe Colborne, 2011 first-round pick & 2012 second-round pick
The haul was massive, but the execution after was terrible. Kaberle was at the end of his run in Toronto, after being one of the steadiest defencemen of his era as a Maple Leaf. Kaberle had spent parts of 12 seasons as a Leaf before being dealt to the rival Bruins. He’d suit up in 24 games down the stretch for the B’s and another 25 on route to winning the Stanley Cup.
Kaberle had 11 assists in the playoffs and was first playing top-four minutes. Colborne, on the other hand, was a prized prospect who had a ton of people aboard the hype train. He never panned out as a Leaf and ended up getting dealt to the Calgary Flames for a fourth-round pick in 2014. Meanwhile, the Leafs ended up trading the Bruins’ first-round pick, along with their own second to move up in the 2011 NHL Entry Draft to select Tyler Biggs. Perhaps the biggest bust in franchise history as Biggs never played a game in the NHL.
David Clarkson dealt to the Columbus Blue Jackets for Nathan Horton
This Leafs’ list is as leafy as it gets. David Clarkson was supposed to be the next coming of Wendel Clark, but the hype was always unfair for the hometown product after he signed a seven-year $36.7 million contract thanks to the very generous Dave Nonis.
Give Nonis credit, he realized the mistake after just 118 games of action and Clarkson was miraculously shipped off to the Blue Jackets for Nathan Horton, who immediately went on long-term injured reserve due to a career-threatening back issue. Clarkson’s contract was off the books and in Columbus he’d go on to play just 26 more NHL games, after being a 30-goal scorer with the New Jersey Devils. There were some ruffles of insurance issues in Columbus regarding Horton’s injury, which likely helped Nonis’ cause.
Maple Leafs acquire Brian Leetch and a conditional fourth-round pick in ’04 from the New York Rangers for Maxim Kondratiev, Jarkko Immonen, ’04 first-round pick & ’05 second-round pick
Kondratiev and Immonen never panned out and neither did either of the drafted players after the deal, meanwhile, Leetch was great as a Leaf. Short but sweet. After being one of the best defencemen of his era, many people forget he even suited up in Toronto and only see him as a lifelong Ranger.
Rightfully so, but you can’t deny the fact he was a huge get for GM John Ferguson Jr at the time, and man it’s hard to type anything nice about JFJ’s work. The big sell here was the fact that Leetch was under contract for the following season, so it wasn’t a pure rental situation, and boy, did the NHL have other ideas though. The unfortunate part was the fact the 2004-05 season never happened.
Regardless, Leetch had 15 points in 15 regular season games and another eight assists in 13 playoff games. If only the Maple Leafs could have run it back the next season. Instead, Leetch signed with the Bruins to finish out his hall-of-fame career.
Maple Leafs acquire Ryan O’Reilly, Noel Acciari, Josh Pillar for a ’23 first-round pick, ’24 second-round pick, ’25 fourth-round pick, Adam Gaudette & Mikhail Abramov
Kyle Dubas went for it and it worked…sort of. The Leafs won their first playoff series in close to 20 years and considering how cash-strapped the team was ahead of the trade deadline, Dubas managed to get the Minnesota Wild involved and surprised everyone with the financial creativity.
Acciari was a solid bottom-six energy forward, meanwhile, O’Reilly made a huge impact in a very short time. He was vocal on the bench and in the room, he calmed the team’s nerves when things were going sideways against the Tampa Bay Lightning and he managed to chip in with nine points in 11 Stanley Cup Playoff games. It’s too bad neither player re-signed with the Leafs, but considering Gaudette and Abramov are career minor-leaguers, Dubas shipped a few lottery tickets off to the Blues and did something in Toronto that hadn’t been done in a very long time.
Maple Leafs bring back Tie Domi from the Winnipeg Jets for Mike Eastwood
Toronto turned a journeyman in Eastwood into one of the league’s best enforcers and biggest showmen in Domi. It was great work by the organization to get Domi back in the mix after drafting him in 1988, trading him to the Rangers in ’90, and then shipping off Eastwood to bring Domi and his vicious left hand back to the Leafs.
Domi would go on to set Leafs records, playing parts of 11 seasons in Toronto after the trade. He’d make headlines, sometimes for all the wrong reasons, but most of all he was a fan favorite who put it all on the line every single shift. Leafs Nation embraced Domi and the feeling was mutual. Domi gave the fans something to cheer about as he was never shy to drop the gloves and throw haymakers. He would also go on to score a career-high 15 goals and 29 points in 2002-03 just two seasons before he retired.
Nevertheless, Treliving has his work cut out for him to pull off some deadline deals before March 8. There’s been some doozies over the years and Leafs fans are curious to see what the Leafs GM can stir up ahead of his first trade deadline in Toronto.
