The Worst Trades In Toronto Maple Leafs History
Photo credit: Jerome Miron-Imagn Images
Today we look at a list of 5 trades from the Toronto Maple Leafs history that the team regrets ever making.
In it's long history, the Toronto Maple Leafs have gone through multiple changes and identities.
From being one of the greatest and most powerful clubs during the Original Six era, the franchise has seen multiple looks and superstar players, yet have not found the right team that gave the team the most important thing of all, a Stanley Cup title.
Despite post-title legends in Darryl Sittler & Doug Gilmour, to modern superstars in Auston Matthews & Mats Sundin, there are good, and bad moments in the franchise's history that define their history to this day.
Here are five trades that impacted the franchise history of the Toronto Maple Leafs:
Toronto Trades Tuukka Rask To Rival Bruins To Keep Justin Pogge
The Toronto Maple Leafs faced a dilemma in it's net at the end of the 2006 season.
The Leafs had a promising young goaltender in Justin Pogge, who had just won Goaltender of the Year in the Western Hockey League and had backstopped Canada to gold at the 2006 World Junior Championship.
The big, imposing 20-year-old Pogge looking like the next big thing in goaltending, and he was property of the Toronto Maple Leafs, who felt they had their future #1 starter.
With Pogge in mind, the Leafs knew they had a possible option to take over long-term in net, but needed a short-term option with their starter that season being 41-year-old Ed Belfour, who had a woeful 3.24 GAA and a .892SV% in 49 games played.
Understanding this, then-Leafs GM John Ferguson Jr. decided they needed a goaltender who could start for next season and perhaps take the reigns until Pogge was ready.
The Leafs settled on Boston Bruins netminder Andrew Raycroft, who was in competition for the starting role in Beantown alongside rookie Tim Thomas.
The Bruins looked for a young netminder in return. Not wanting to give up their future #1 in Pogge, Ferguson traded their first round pick in the 2005 NHL Draft.
Tuukka Rask as the netminder for Finland had been beat by Pogge's Canada at the World Juniors, although it was Rask who ultimately was voted as the tournament's top netminder despite a standout performance by Pogge. Despite this, Toronto had trust in Pogge and moved the expendable Rask to Boston.
Pogge was quickly the starter in the AHL for the Toronto Marlies, showing some promising ability in his first two seasons.
Pogge was given a seven game stint with the Leafs in the 2008-09 season, but that would be as good as things would go for the Canadian. He would struggle to continuously be an AHL starter, and never made the big leagues again.
In 2012, Pogge moved to play in Italy, spending a decade across Europe in multiple leagues before finally retiring in 2023. As for Rask, most hockey fans know about what he's accomplished.
Rask would actually debut before Pogge, and after winning the Stanley Cup in 2011, became one of the league's top goaltenders. A Vezina winner in 2014, a two-time All-Star, as well as an Olympic bronze medalist, Rask has carved out a potentially Hall of Fame career.
Pogge has still had a respectable and long pro career, and is now the Goaltending coach for the AHL Abbotsford Canucks.
Andrew Raycroft would play a whopping 72 games in 2006-07 for Toronto but struggled heavily next season and was placed on waivers and bought out, not being a starting netminder in the NHL again.
Andrew Raycroft would play a whopping 72 games in 2006-07 for Toronto but struggled heavily next season and was placed on waivers and bought out, not being a starting netminder in the NHL again.
As an extra pie to the face, the Bruins were not planning to bring back Raycroft, for next season, and had the Leafs waited, they could have had their starter without giving up one of the league's best goaltenders.
Toronto Gives Up Jared McCann In Expansion Draft Blunder
In the 2021 NHL expansion draft, the Toronto Maple Leafs could only afford to protect a certain amount of players, leaving a few players the team believed in vulnerable to be swooped up by the league's newest franchise, the Seattle Kraken.
The Leafs were one of many teams fielding offers from other teams for players they knew they couldn't protect but other teams might. Toronto swung a deal with the Pittsburgh Penguins, acquiring McCann in exchange for a seventh-rounder and Filip Hallander.
The deal seemed like a bargain for the Leafs, getting McCann, who had 32 points in just 43 games. However, the team delivered a shock.
Despite acquiring McCann, the truth is that the plan for Toronto didn't involve him at all. Toronto had taken McCann, to have him be taken by Seattle so Toronto could keep Alex Kerfoot and Justin Holl, the latter of whom was a subject of criticism that season over his inconsistent play.
McCann would dominate with the Kraken, scoring 40 goals in 2022-23 with Seattle, suddenly one of the NHL's top goal scorers.
Both Kerfoot and Holl would go on to play two more seasons in Toronto before signing a three-year contract with the Arizona Coyotes and Detroit Red Wings respectively, neither of whom matched the highs of McCann.
Throwaway Prospect Becomes Future 40-Goal Scorer After Departure
Prospects aren't always predictable. Sometimes a first round pick can struggle to grow and become what they were hoped to be, and sometimes a player who goes undrafted grows their game to the NHL level and becomes a star.
If the Toronto Maple Leafs had foresight, they could have seen one easily movable asset was a future top player, and they'd wish they were looking a bit clearer at their whole roster.
Hoping to turn around the tides of a struggling Leafs team, new Toronto GM Lou Lamiorello made a major trade acquiring forward Michael Grabner from the New York Islanders for five players that was meant to get rid of contracts that were easy to move on from.
Two of those acquired by the Isles, Taylor Beck and Chris Gibson, would play a handful of games for the team to little note, but it was a player who made the most impact without playing in New York.
Traded to the Tampa Bay Lightning in 2017, Carter Verhaeghe was now apart of Tampa's system in the AHL with the Syracuse Crunch, who made the Calder Cup finals a year prior.
After a decent year in Syracuse with 48 points in 58 games, Verhaeghe broke out next season with a league leading 34 goals and 82 points in 76 games.
That performance led to Verhaeghe, only 24, making the Lightning roster the next season, making him a full-time NHLer. Moving to the nearby Florida Panthers as a free agent did even more wonders, being a consistently improving player, culminating in a 42-goal season in 2022-23.
Verhaeghe would go on to win two Stanley Cups, in 2020 with Tampa Bay and 2024 with Florida.
Grabner, on the other hand, would spend just one season in Toronto, being a reliable penalty killer but with just 18 points in 80 games for the Leafs.
He would hit 40 points the next season with the New York Rangers, but did not come close to being what Verhaeghe had become, going from a spare part in a contract clearing to a Stanley Cup winner and a dominant NHL player.
Leafs Stars Pushed Out After Public Conflicts With Management
Depending on who you ask from that time, Harold Ballard was the devil whose personal hell was the offices of Maple Leaf Gardens. Others have much nicer things to say.
One of the forgotten aspects of Ballard's ownership of the Toronto Maple Leafs was the saga that ended the partnership between the Leafs and legendary captain Darryl Sittler, a conflict that went back years before he was finally moved out from the city.
Sittler had continuously dealt with stress in his time with Toronto. The team was a difficult environment that as the team's top player, Sittler had to navigate harder than anyone.
Ballard had difficulties with Alan Eagleson, then the NHLPA Executive Director and former agent for Sittler, who was close with Eagleson. This animosity towards Eagleson from Ballard led to the relationship with Sittler being strained to the point of Sittler repeatedly threatening to quit on the team.
Retaliating to Sittler's bitterness over the team, Ballard and GM Punch Imlach worked to reduce Sittler & Eagleson's influence in the locker room, trading Sittler's close friend Lanny McDonald to the Colorado Rockies, a move that angered the captain so powerfully that he ripped up his own "C" from his jersey, playing without it.
Attempts to work their relationship owned proved unsuccessful in the long run, and the Leafs finally moved on from Sittler in 1982, who by that point was ready for a fresh start, getting his wish with a trade to the Philadelphia Flyers.
The trade was not by any means a memorable one, the Leafs not getting much back for Sittler. McDonald would go on to be a Stanley Cup Champion with the Calgary Flames in 1989.
It was these two trades that help lead to the downfall of the Toronto Maple Leafs in the 1980's, and greatly contributed to the difficult years that would lie ahead, a shell of the once great franchise.
Leafs Move Chance For Defenseman Of The Future
Floyd Smith had been through a lot in the 1980's. The head coach of the Leafs, a car accident that killed two pedestrians and had Smith charged with impaired driving, in which he was acquitted, would derail his career in coaching as he had been left unable to perform his role.
He would stay in the organization as a scout before being given another chance with prominence in the team as GM in 1989. Ready to make moves to take the struggling Leafs a valuable team once again, Smith took a major risk.
The Toronto Maple Leafs traded a first round pick in the 1991 NHL Entry Draft to the New Jersey Devils in exchange for defenseman Tom Kurvers, a first pairing defender with a strong offensive game, the type of player that can be a game changer.
Kurvers looked the part in the 1989-90 season with 52 points in 70 games, but next season was a dud, with just three points in 13 games. Kurvers was traded to the Vancouver Canucks, where he'd find his offense again with 27 points in 32 games, but would become a journeyman defenseman.
Luckily for Toronto, the pick was not the first overall selection which was for generational prospect Eric Lindros, it was third overall. The Devils used the pick on defenseman Scott Niedermayer.
One Norris Trophy, three Stanley Cups and a Hockey Hall of Fame induction later and the trade looks like a disappointment for Toronto who could have had a superstar defenseman without trading for Kurvers, who ultimately did not fill that role as he could have.
Although, who knows what they would have done, they could have easily had gone with defenders Scott Lachance and Aaron Ward, taken two spots later, or the sixth overall pick, Peter Forsberg.
| POLL | ||
NOVEMBRE 29 | 581 ANSWERS The Worst Trades In Toronto Maple Leafs History Which player traded away by the Toronto Maple Leafs would have made the most impact? | ||
| Tuukka Rask | 278 | 47.8 % |
| Carter Verhaeghe | 97 | 16.7 % |
| Jared McCann | 31 | 5.3 % |
| Scott Niedermayer | 175 | 30.1 % |
| List of polls | ||
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