Top 10 Best Trades in Toronto Maple Leafs History
The Toronto Maple Leafs were shakers and movers this off-season and it got me thinking about some of the best trades in team history.
The Toronto Maple Leafs have been incredibly busy lately, having already made five trades this off-season. Although some transactions were bigger than others, it’s hard to argue that any of the moves made were bad.
In fact, the ability to move Kasperi Kapanen and Andreas Johnsson, while getting real assets in return was remarkable. Both players are former 20-goal scorers, but the Leafs were able to replace them cheaply (Vesey, Thornton, Barabanov, Robertson) and then trade them for prospects while getting salary cap relief.
Within the Kapanen deal, the Toronto Maple Leafs acquired an AHL-level defenseman, and two potential A-level prospects. Filip Hallander will become an NHLer eventually, while Rodion Amirov, who the team selected with the draft pick that the Penguins gifted them could be one of the biggest steals of the Draft.
Although the New Jersey Devils package for Andreas Johnsson wasn’t as steep as what the Pittsburgh Penguins gave up for Kasperi Kapanen, Kyle Dubas was once again able to get a quality piece in return. The Toronto Maple Leafs were able to clear all $3.4M of Johnsson’s contract, while acquiring Joey Anderson, who by all accounts will be a roster player. Maybe not this season, but next year for sure.
Overall, the Toronto Maple Leafs roster is going to look a lot different next year, thanks to a few great trades. Let’s look back at the best 10 trades in Toronto Maple Leafs history.
#10. The Rick Vaive Trade
The Trade:
- Toronto Maple Leafs acquire: Rick Vaive and Bill Derlago
- Vancouver Canucks acquire: Dave “Tiger” Williams and Jerry Butler
There was almost nobody as beloved as Dave “Tiger” Williams and although it hurt the fan-base to trade him to Vancouver, the Toronto Maple Leafs got the best player in Rick Vaive.
Vaive had only played one NHL season before the Vancouver Canucks shipped him to Toronto. I know fighting and tough-guys were valued a lot more back in the day, but did Vancouver never watch Vaive play before they traded him? A few years prior in junior, Vaive had 76 goals in 68 games played in the QJMHL. Not only was he a goal-scoring machine, but had 155 points and 199 PIMs!
Not only could he score whenever he wanted, but he wasn’t afraid to drop the gloves, either.
After being traded to the Toronto Maple Leafs, Vaive became the only player in team history to have three straight 50-goal seasons and his 54 goals scored in the 1981-82 season, still stands as the single-season record. Although many people think he’s overrated, he had seven straight seasons of 30 or more goals, which is an incredible achievement.
Although Rick Vaive is the more known player in this trade, the team also acquired Bill Derlago, who also had a great career in Toronto. During six seasons with the Toronto Maple Leafs, Derlago scored 30 or more goals four times, including a career-high 40 tallies in the 1983-84 campaign.
#9. Leafs Get Freddie Andersen From Anaheim
The Trade:
- Toronto Maple Leafs acquire: Freddie Andersen
- Anaheim Ducks acquire: 2016 First Round Pick (Sam Steel) and 2017 Second Round Pick (Maxime Comtois)
Sam Steel and Maxime Comtois are turning into full-time NHL players, but they’re not a top-10 goaltender in the league. And that’s exactly what Freddie Andersen is. I can understand the criticism towards Andersen over his tenure in Toronto, but I’m a supporter.
Sure, he hasn’t won a playoff series, but have you seen the defense in front of him? It’s absolutely brutal. I’m going more on eye-test than numbers right now, but if you watch Andersen play, you can understand that he’s a good goalie, just based on his poise.
The best goalies in the game have this calmness about them and the best way to describe it, is that it’s the complete opposite of Reimer. When you watched Reimer play, he looked like a road-hockey goalie at times. Sure, he could make a few saves when he needed, but it was absolute chaos and terrifying to watch as a fan.
With Freddie Andersen, you don’t see this. If a goal goes in, it’s usually because of a defensive breakdown. He’s completely stoic, just like Carey Price. He may not be as talented as Price, but he has that same composure that’s hard to teach.
Overall, the Leafs barely gave anything up in exchange for a number-one goalie and Lou Lamoriello deserves a ton of credit for making this deal.
#8. Trading a Hall-of-Famer for Ian Turnbull
The trade:
- Toronto Maple Leafs acquire: Ed Johnston and 1973 1st Round Pick (Ian Turnbull)
- Boston Bruins acquire: Jacques Plante and 1973 3rd Round Pick (Doug Gibson)
I know that Jacques Plante is one of the greatest goalies to ever live, as he racked up seven Vezina Trophies and one Hart Trophy, but this was such a terrible trade from the Boston Bruins perspective.
Plante was 44-years-old(!!!) when the Toronto Maple Leafs traded him to Boston. Imagine this trade going down today? If a General Manager made this move today, they would immediately get fired. A first-round pick is incredibly valuable but think about how better it was back in 1973. There were only 16 teams in the NHL so you were guaranteed a great pick, even if you won the Stanley Cup.
Speaking of great players in the first round, the Toronto Maple Leafs pick they got in exchange for Plante turned into Ian Turnbull, who happens to be one of the best offensive defenseman to ever play in Toronto.
Turnbull’s 1976-77 season is still the greatest season by a defenseman in Toronto Maple Leafs history, as he finished with 22 goals and 79 points. In nine seasons, Turnbull had 55 or more points in five of those seasons, and the combination and him and Borje Salming were a force on the Leafs blue-line during the 1970s.
#7. Bryan McCabe is Stolen from Chicago
The trade:
- Toronto Maple Leafs acquire: Bryan McCabe
- Chicago Blackhawks acquire: Alexander Karpovtsev and 2001 4th Round Pick (Vladimir Gusev)
Bryan McCabe was a decent defenseman before getting traded to the Toronto Maple Leafs, but turned into an amazing one, once he wore the blue-and-white. I’m not sure if it’s because he got to play closer to home (he’s from St. Catharines, ON), but playing in Toronto rejuvenated his career and made this trade a steal.
McCabe played seven seasons in Toronto and was a top-pairing defenseman, typically paired with Tomas Kaberle. As every Toronto Maple Leafs fan remembers, Kaberle would always be the one to fake shots at the point, then pass it over to McCabe for the one-timer, who would benefit immensely because of this.
They were the perfect ying-and-yang combination on the blue-line and were part of a ton of great early 2000s memories in Leafs-Land. Not only did the Toronto Maple Leafs get the best player in the trade, but Karpovtsev and Gusev didn’t really amount to anything. Gusev never played an NHL game, while Karpovtsev only scored seven NHL goals after being traded.
This was a huge win for the Toronto Maple Leafs and McCabe is still loved in the city. Obviously the team never won the Stanley Cup, but he was part of the last team that had a good chance at doing so, when the team lost in the Eastern Conference Finals.
#6. Former Top-Five Draft Picks Traded One-for-One
The trade:
- Toronto Maple Leafs acquire: James van Riemsdyk
- Philadelphia Flyers acquire: Luke Schenn
In terms of a one-for-one trade, you can’t fleece a team more than how the Toronto Maple Leafs conned the Philadelphia Flyers. Both players were in need of a change of scenery, and Toronto hit the jackpot with this deal.
Five years prior, James van Riemsdyk (JVR) got drafted second-overall, right behind Patrick Kane. At 6-foot-2, 215 pounds, he was a big-body forward who could score and looked like he’d transition easily to the NHL game. Although he had three good seasons to kick-start his career, the Philadelphia Flyers decided to move on from him in exchange for defense.
Similar to JVR, Luke Schenn had been drafted high (5th overall, 2008 NHL Entry Draft), but his play started to decline in the big hockey market of Toronto. Schenn was more of a defensive defenseman anyways, who relied upon his big body to hit and be a physical presence, but his game was unfortunately diminishing.
After the teams swapped the young players, JVR’s stock began to rise, while Schenn’s did the opposite. The Toronto Maple Leafs won this trade by a landslide as Schenn turned into a bottom-six defenseman, while JVR became a top-six forward.
Over his six campaigns in Toronto, JVR had four 20-goal seasons, including a career 36-goals scored in the 2017-18 season.
#5. Zach Hyman for Greg McKegg
The Trade:
- Toronto Maple Leafs acquire: Zach Hyman
- Florida Panthers acquire: Greg McKegg
Now that we’ve seen the type of player that Zach Hyman has turned into, it’s hard to think that the Toronto Maple Leafs acquired him back in 2015, in a one-for-one trade for Greg McKegg.
McKegg has turned into a journeyman, having now played for six NHL teams in the past six years. He’ll continue to be a fourth-line player who will be in and out of the line-up every night, but he’s not going to be a difference maker. Personally, I think he would have been a great fit back on the Toronto Maple Leafs, but he’s no Zach Hyman.
Hyman has always been a late-bloomer. He played all four years of NCAA hockey with the University of Michigan and it wasn’t until his last season, where things took off. During his senior season, he was named a finalist for the Hobey Baker Award after scoring 54 points in 37 games.
After that spectacular season, Hyman opted to become a Free Agent, instead of signing with the Florida Panthers who drafted him. As a result, the Toronto Maple Leafs were able to trade Greg McKegg to Florida in exchange for Hyman’s rights and the team worked out a contract not long afterwards.
As a Toronto native, the Toronto Maple Leafs lucked out that Hyman wanted to sign in his hometown, and that the Florida Panthers wanted to make a deal. Hyman has finished with back-to-back 20-goal seasons and is one of the most reliable players on the team.
Night-after-night, you know you’re going to get a hard-working player who can help on the penalty-kill and potentially score. He’s been an important piece paired beside Auston Matthews most nights and the ability to have traded a fourth-line player for him, makes this one of the best trades in team history.
#4. Turk Broda for $8,000
The Trade:
- Toronto Maple Leafs acquire: Turk Broda
- Detroit Red Wings acquire: $8,000
Back in 1936, $8K was a lot of money, but it was worth every penny to acquire one of the greatest goaltenders in Toronto Maple Leafs history.
The Detroit Red Wings were fine with giving up Broda, because they already had two goaltenders ahead of him and could afford trading him. Although they won the Stanley Cup one year after trading Broda, this is one of the worst deals in history.
When you think of the Toronto Maple Leafs, there are a handful of names that are synonymous with the franchise and Turk Broda is one of them. After arriving in Toronto, Broda would play 629 games, leading the team to five Stanley Cup championships and individually winning two Vezina Trophies.
For roughly 15 years, Broda was the starting goaltender for the Toronto Maple Leafs and they had a chance to win every game he was in the net for. That may be the best $8,000 that anyone has ever spent in professional sports history, because without Broda’s services, who knows how many championships the team actually would have own.
#3. Leafs Trade Former Captain for Future Captain
The Trade:
- Toronto Maple Leafs acquire: Mats Sundin, Garth Butcher, Todd Warriner and 1994 1st Round Pick (Nolan Baumgartner)
- Quebec Nordiques acquire: Wendel Clark, Sylvain Lefebvre, Landon Wilson and 1994 1st Round Pick (Jeff Kealty)
It’s always tough to trade Wendel Clark, who was one of the most loved players in Toronto Maple Leafs history, however this time was easier. The reason it was easy to deal with was because Clark returned to the Leafs two years later, and the team received a future Hall-of-Famer in Mats Sundin..
Both Clark and Sundin were former first-overall picks in the NHL Entry Draft, so this is a huge trade in NHL history. Clark was a fan-favourite in Toronto because not only could he fight and hit, but he could score. He was the perfect power-forward and a player that was easy to love. Sundin on the other hand was a big-man from Sweden, who was much more skilled than physical.
The fact that Quebec traded Sundin away still blows my mind. Sundin was coming off an 84 and 114 point season and was living up to his first-overall selection status. After being traded to the Toronto Maple Leafs, Sundin didn’t skip a beat. Sundin had 13-straight 20-plus goal seasons, including 10 seasons of 30-or more goals.
Just like Wendel Clark had been previously, Sundin was named the captain of the team and helped lead the Leafs to two Eastern Conference Finals appearances. For the Toronto Maple Leafs fans born after 1990, Sundin is their almighty god and one of the greatest players in team history.
#2. Conn Smythe’s Horse Helps Team Acquire King Clancy
The Trade:
- Toronto Maple Leafs acquire: Francis “King” Clancy
- Ottawa Senators: Eric Pettinger, Art Smith and $35,000
The reason I have this trade so high on this list is because of the backstory. It’s such an incredible narrative and if you don’t know the reasoning behind this transaction from 1930, let me summarize it for you.
The Toronto Maple Leafs were looking to acquire King Clancy, but the Ottawa Senators (who Clancy was currently playing for) weren’t going to give him up for cheap. In fact, the Senators wanted $35,000 in cash and a couple players for Clancy. Unfortunately the Leafs didn’t have that type of cash. Yet.
The architect behind the Toronto Maple Leafs at the time was Conn Smythe and all he wanted was to acquire Clancy and win the Stanley Cup. In order to win some cash, Smythe took a gamble and purchased a cheap race-horse named “Rare Jewell” hoping it could win big. However, in every race it entered, it finished near last place and looked lost, until the last race it ever ran.
Racing at Woodbine in Toronto, “Rare Jewell’s” odds were 107-1, which meant a $1 bet pays out $107. In a what would be described as a miracle, Smythe’s horse won the race and as a result, that victory secured him $12,000. He’d won $3,750 for the winner’s purse, but an extra $9,372.70 from betting on the horse to win, place and show.
The fact that Conn Smythe was able to purchase a cheap horse and actually turn it into a luxurious financial investment is amazing. According to the inflation rate from 1930 to 2020, that $12,000 is equivalent to $186,000 today, which is an outrageous number to win on a horse-race.
One year after acquiring Clancy, Smythe got what he was looking for and the Toronto Maple Leafs won the Stanley Cup, which makes this trade so much fun.
#1. Doug Gilmour Joins Leafs in Blockbuster Deal
The Trade:
- Toronto Maple Leafs acquire: Doug Gilmour, Jamie Macoun, Kent Manderville, Ric Nattress and Rick Wamsley
- Calgary Flames acquire: Craig Berube, Alexander Godynyuk, Gary Leeman, Michel Petit and Jeff Reese
There was a lot of moving parts in this trade, but the main focus is that the Toronto Maple Leafs acquired Doug Gilmour, who is arguably more loved than any other player in team history.
To this day, the Gilmour #93 jersey is probably the most-worn sweater at Scotiabank Arena of a player not currently on the roster, and it makes sense why. Once Gilmour arrived in Toronto, he instantly become a superstar.
His first two full seasons in the Blue-and-White are two of the best seasons in Toronto Maple Leafs history. Gilmour finished with 127 points in his first full season, which is still the highest single-season point total in Leafs history.
During those two years from 1992-1994, Gilmour was on-top of the hockey world. He was one of the top-five players in the NHL and put the team on his back, all the way to the Western Conference Finals. Gilmour kept his incredible regular season going into the playoffs, finishing with 35 points in 21 playoff games, as his team came ever so close to making the Stanley Cup Finals for the first time since 1967.
The buzz around the city was electric and Gilmour was the reason for it. The team had some good players, but he was the best by a mile, finishing with 53 more points than the second-highest scoring player on the team. To put him into comparison, he was kind of like Nathan MacKinnon with the Colorado Avalanche this season, putting the team on his back.
Next. Rasmus Sandin Needs to be in the NHL. dark
The ability to get Gilmour for those two magical seasons alone, makes this the greatest trade in team history.