The Most Regretted Trades By The Toronto Maple Leafs

The Toronto Maple Leafs are a storied franchise in the NHL, having begun life as the Toronto Hockey Club back in 1917 and being part of the Original Six era. Through over 100 years of existence, the team has participated in many trades; some have been great, while others not so much.

Trades can always be a gamble, and some are done for genuine reasons. Others, though, should not have been done regardless of whether or not the return was acceptable at the time. Some trades in Leafs history truly set the franchise back and had history-altering impacts for different reasons.

So what were three of the most regrettable trades made in Toronto Maple Leafs history?

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Rask For Raycroft

Ask any Maple Leafs fan of the past twenty years what the worst trade is, and this one will certainly be atop the list for many people. In the 2005 NHL Draft, with the 21st overall pick in the first round, the Toronto Maple Leafs selected a player who should have been the future of the team in net for many years to come: Tuukka Rask.

The season after his draft, Rask put up impressive numbers with Ilves of the Finnish SM-Liiga: a 12-8-7 record, a .926 save percentage, and a goals-against average of 2.09. Ilves did not do well in the playoffs, but Rask still had a .924 Sv% and a 2.33 GAA in three games.

This should have given the Leafs belief that they had the real deal and, with just a bit more experience, he could step up to the NHL team in a relatively short time. However, the Leafs were impatient and believed that Justin Pogge, their third-round pick in 2004, may be the better prospect after an impressive year with the WHL’s Calgary Hitmen and a dominant performance for Team Canada at the World Junior Championships.

So, on June 24th 2006, the Leafs opted to acquire an NHL-ready goaltender in Andrew Raycroft from the Boston Bruins, sending Rask the other way.

The trade should not have happened. Full stop. The Leafs spent a first-round pick on Rask and should have played the patient, waiting game rather than leaping to acquire a goaltender already playing in the NHL. Raycroft won the Calder Trophy in 2003-04, but when the NHL resumed in 2005-06 after the lockout, he struggled immensely and was demoted to third string, playing 30 games but earning just eight wins for the Bruins.

That should have been enough to tell the Leafs that Raycroft would not be the saviour they hoped. Being demoted by the Bruins should have given the Leafs pause that perhaps they should be happy with their prospect depth, and potentially even one day have a strong tandem of Rask and Pogge together.

Raycroft played 72 games in his debut season with the Leafs, earning 37 wins, but the team missed the playoffs, and he played just 19 games the following year, losing out to Vesa Toskala, before he was out of Toronto.

Pogge also did not pan out, playing just seven games in the NHL with the Leafs before moving to the Anaheim Ducks and later the Phoenix Coyotes before spending the rest of his career in Europe. Rask? Well, he turned into a Vezina winner, a Jennings winner, a two-time Stanley Cup champion, an Olympic bronze medallist, and the nightmare of the Leafs until his retirement in 2022.

Tom Kurvers

At the start of the 1989-1990 season, the Toronto Maple Leafs were looking to add a defenceman to the roster, having lost Börje Salming to the Detroit Red Wings in free agency earlier that summer. Tom Kurvers had bounced around the league a bit across his first five years in the league, playing with the Montreal Canadiens, Buffalo Sabres, and New Jersey Devils by the start of the 1989-90 campaign.

After putting up 16 goals and 66 total points in 74 games in 1988-89, the Leafs decided that Kurvers could be their long-term replacement for the great Swede and swapped a 1991 first-round draft pick in exchange for him. The hope was that, with Kurvers stepping into the lineup immediately, the Leafs would be a solid playoff team in 1990-1991, so the pick they sent would be late in the round.

Unfortunately, the Leafs were not a sound team. They made the playoffs in Kurvers’ first season, seeing the defenceman hit 15 goals and 52 points in 70 games, but the following year the team missed the post-season with a 23-46-11 record (the second-worst record that year).

As a result, the Leafs’ pick sent to the Devils became the third-overall pick, which landed the American team future four-time Cup champion, Norris Trophy winner, Conn Smythe winner, and Hall of Famer Scott Niedermayer.

There’s belief that the Leafs could have landed the first-overall pick that year had they had their own first-round pick, and even if they didn’t land Eric Lindros, or even decide not to pick Niedermayer if they still held the third pick, there were many players they could have selected in that draft class that could have had a significant impact on the team.

Peter Forsberg went sixth that year, Alexei Kovalev went 15th, Ray Whitney went 23rd overall, and Markus Nasland went 16th overall. If the Toronto Maple Leafs had held on, they could have landed a Hall of Famer on either side of the ice.

Kurvers, meanwhile, lasted just 19 more games in the 1990-91 season and was traded to the Vancouver Canucks for Brian Bradley, who joined the Tampa Bay Lightning in 1992 and had his best years there until retiring in 1998.

Darryl Sittler to the Flyers

Sometimes a trade can be regrettable because the return isn’t enough for the player or the picks sent the other way. Other times, the circumstances around the trade make it especially regrettable, and that’s the case with the deal that sent Darryl Sittler to the Philadelphia Flyers.

Sittler should have been a one-team player. He was the Leafs’ best player, he was captain of the team, and by the end of his tenure in Toronto, he had 916 points (389 goals, 527 assists) in just 844 games. He still sits third in Leafs’ history for goals and assists, with his combined points total good for second in franchise history, and he was only traded due to tensions between him, his agent, and infamous Leafs owner Harold Ballard and then-GM Punch Imlach.

Ballard and Imlach did much to limit Sittler’s influence on the team, trading away close friend and teammate Lanny McDonald, leading to Sittler famously cutting the ‘C’ off of his jersey. Sittler did return the following season with it back on, but even after Imlach left, things deteriorated further between him and ownership, and he waived his No-Trade Clause for a move to either the Philadelphia Flyers or Minnesota North Stars.

Eventually, a deal was struck with the Flyers, with the Leafs receiving Rich Costello, a Hartford Whalers second-round pick in 1982, and future considerations. With the second-round pick, the Leafs selected Peter Ihnačák, who played 417 NHL games, all with Toronto, while registering 267 points (102 goals, 165 assists).

Costello lasted just 12 games with the Leafs, and the future considerations turned into Ken Strong, who made just 15 NHL appearances, all with the Leafs. Ihnačák returned to Europe and, after retiring, rejoined the Leafs as a European scout for many years.

The return for Sittler, who played two-and-a-half more years in the NHL with the Flyers and then the Detroit Red Wings, was ultimately very disappointing for a player who meant so much to the history of the team. However, it’s also the fact that he was essentially forced out that sees this deal land on this list.

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