Top 10 Worst Trades in Toronto Maple Leafs History

The history of the Toronto Maple Leafs has had many of ups and downs, especially via trades.

Since the Toronto Maple Leafs franchise has been around for over 100 years, they’re bound to make a few dumb moves. Although the best-of list was much more fun to talk about it, these terrible trades make being a fan so special.

If you’re like me, when your favourite team makes a trade, I immediately agree with the decision. I’m not in the war-room, scouting, or playing the sport at a professional level, so who am I to judge the decision so quickly? I give the benefit of the doubt to the General Manager who made that move, assuming that the trade will work out in my teams favor.

When your favourite team is the Toronto Maple Leafs, that’s a tough pill to swallow. For years, the team has made some very bad decisions. Whether it’s through coaching, management, scouting, free agency, drafting or trading, there were some bleak years in Leafs-Land.

However, even when each transaction happened, I tried to stay optimistic. But after revisiting this list, it’s tough to understand why I felt that way.

Fortunately for the newest regime, most of the decisions they’ve made have paid off. There are still a few that I shake my head at, but the majority have been good. You’re not going to go 100 percent on your trades, but if you can hit between 80-90 percent, you’re going to have an incredibly successful career.

Speaking of which, let’s take a look at the history of the Toronto Maple Leafs and break down the top 10 worst trades in team history.

#10. Leafs Send Their Best Player to Philadelphia

The Trade:

• Toronto Maple Leafs acquire: Rich Costello, future considerations and 1982 2nd Round Pick (Peter Ihnacak)
• Philadelphia Flyers acquire: Darryl Sittler

You shouldn’t trade the greatest point-producer in Toronto Maple Leafs history, but you don’t tell Harold Ballard what to do.

The relationship between Sittler and Ballard wasn’t pretty. Sittler felt more betrayed by Ballard with every passing moment. The controversial owner fired popular head coach Roger Neilson and then decided to trade one of Sittler’s best-friends, Lanny McDonald.

The relationship continue to worsen daily, until Sittler agreed to leave. As a local kid, living his dream playing for the Toronto Maple Leafs, while excelling at it, it’s not like he wanted to move on, but it was necessary. Ballard made a lot of terrible moves, but ruining the relationship with Sittler was one of his worst decisions.

The Toronto Maple Leafs received Peter Ihnacak in the package for Sittler and although he had a good few seasons, nobody could replace the captain. Sittler only played for another four seasons after he was traded from Toronto, but would still rack up great point-totals, scoring 43 goals and registering 83 points in his second season in Philadelphia.

#9. Fan-Favourite Nazem Kadri Gets Shipped to Colorado

The Trade:

• Toronto Maple Leafs acquire: Tyson Barrie, Alex Kerfoot and 2020 6th Round Pick (Joe Miller)
• Colorado Avalanche acquire: Nazem Kadri, Calle Rosen and 2020 3rd Round Pick (Jean-Luc Foudy)

We can argue about whether or not Tyson Barrie was actually a very good defenseman when Sheldon Keefe arrived and rave over the defensive numbers that Alex Kerfoot produces, but I needed to put this trade on my list, because of Kadri.

The last few regular seasons of Kadri were amazing but his playoff disaster was the reason the team needed to move on from him, and I understand that, but, man! To look what he’s doing in Colorado right now as the second-line centre, makes me so upset that the team didn’t push him into that role in Toronto.

He’s way too expensive as the third-option, but would you rather have Kadri at $4.5M or John Tavares at $11M as your second-line centre? Tavares is much better, but is he really $6.5M better than him? Think about what the team could have done with that extra cash if they had it.

I love John Tavares and am thankful he’s a member of the Toronto Maple Leafs, but I think the team would have been in a much better situation depth-wise if they had Kadri in there instead.

#7. Larry Murphy Gets Sent to Detroit

The trade:

• Toronto Maple Leafs acquire: Future Considerations
• Detroit Red Wings acquire: Larry Murphy

Larry Murphy was essentially the modern-day Jake Gardiner. Both players were immensely skilled offensively, but were ridiculed during their time in Toronto. The fan-base unfairly sent both players packing, despite their resume.

What makes this trade so terrible, is that the team got nothing in return for Murphy. They essentially shipped one of the best offensive defenseman all-time to one of the best teams in the NHL for nothing. When Murphy arrived in Detroit, he was brilliant.

In fact, he won back-to-back Stanley Cups. I know the Toronto Maple Leafs weren’t great when they had Murphy for 1.5 seasons, but they were just about to be. He would have been reliable on the team’s blue-line and someone who could have provided a ton of experience and talent for the team, as they made their own run at a Stanley Cup.

The fact that the Toronto Maple Leafs traded the 36-year-old defenseman who making over $2M per season wasn’t the issue, but it’ll continue to be the fact they never got anything in return. For someone so talented, you think they could have shipped him somewhere for a prospect or draft pick, but instead let the future Hall-of-Famer walk for nothing.

#6. Leafs Give Up Two Studs for One Dud

The Trade:

• Toronto Maple Leafs acquire: Lee Stempniak
• St. Louis Blues acquire: Carlo Colaiacovo and Alexander Steen

Even at the time, this trade didn’t make a ton of sense. Sure, Stempniak had previously scored 27 goals in a season, but that was a fluke. Even a one-for-one trade for Stempniak for Steen would have been bad, but to throw in Colaiacovo as well, I couldn’t understand it.

Both Stempniak and Colaiacovo were previous first-round picks of the Toronto Maple Leafs, but the team decided they needed to acquire the one-dimensional Lee Stempniak instead. Colaiacovo may have had injury problems throughout his career, but he turned into a steady defenseman and had his best years in St. Louis.

Stempniak never scored 20 goals in the NHL again, while Steen had four 20-goal seasons, including a 33-goal campaign in 2013-14. Not only was this trade so lopsided, but Stempniak was flipped to Phoenix only two seasons after getting traded for.

#5. Randy Carlyle Gets Traded and Becomes NHL’s Best Defenseman

The Trade:

• Toronto Maple Leafs acquire: Dave Burrows
• Pittsburgh Penguins acquire: Randy Carlyle and George Ferguson

Randy Carlyle may be most-known for coaching the Toronto Maple Leafs (“Good one, Randy”) instead of playing for them, but the 64-year-old was drafted by the team in 1976 and played two seasons in Toronto.

I’m not sure what the team was thinking when they made this move. It was during the Harold Ballard Era, so I mean anything was possible back then and nobody was safe. However, the Sudbury, ON native had ripped up junior hockey in his hometown before joining the Toronto Maple Leafs and looked like a great prospect.

However, after not producing much at the NHL-level, two years later Carlyle was sent to the Pittsburgh Penguins with George Furgson for an aging veteran defenseman named Dave Burrows.

Burrows was at the end of his career, while Carlyle was just getting started, and boy did he ever take off. Two years after getting traded from the Toronto Maple Leafs, Carlyle turned into one of the best defenseman in the NHL. His 1980-81 season will always be remembered in Pittsburgh, as he scored 16 goals, registered 83 points and won the Norris Trophy.

And it’s not like Carlyle was a flash in the pan or anything that one season. For the next decade after the Toronto Maple Leafs moved on from him, he continued to produce year-after-year. Even when he got traded to the Winnipeg Jets, he continued to have a great career, playing over 1000 NHL games.

#4. Leafs Give Up on Future Vezina Trophy and Conn Smythe Winner

The Trade:

• Toronto Maple Leafs acquire: 1973 First Round Pick (Bob Neely) and Doug Favell
• Philadelphia Flyers acquire: Bernie Parent

The history of Toronto Maple Leafs goaltenders in deep. From Johnny Bower to Curtis Joseph, the list goes with regards to great net-minders. However, that list could have been a little longer if they decided not to move on from a future Conn Smythe trophy winner named Bernie Parent.

Splitting time with Jacques Plante, the Toronto Maple Leafs decided to keep Plante (who was 43-years-old) instead of the 26-year-old Parent and shipped him to Philadelphia after only two seasons. And it may be one of the worst decisions they ever made.

In back-to-back years after leaving the Toronto Maple Leafs, Parent joined the “Broad Street Bullies” and not only won back-to-back Stanley Cup championships, but he was the Conn Smythe winner in both. To put a cherry on top of everything, he was also named the NHL’s best goaltender, taking home the Vezina Trophy in both championship seasons.

So essentially, the Toronto Maple Leafs moved on from the best goaltender in the world for a decent defenseman and mediocre net-minder. Who knows if Parent would have been able to win a Vezina Trophy in Toronto, but that’s tough to see.

ST PAUL, MN – JUNE 24: 22nd overall pick Tyler Biggs by the Toronto Maple Leafs  . (Photo by Bruce Bennett/Getty Images)

#3. Leafs Take “Biggs” Swing and Miss

The Trade:

• Toronto Maple Leafs acquire: 2011 1st Round Pick (Tyler Biggs)
• Anaheim Ducks acquire: 2011 1st Round Pick (Rickard Rakell) and 2011 2nd Round Pick (John Gibson)

Ughh, how many times do we have to visit this trade? Every time I talk about it, I cringe. How could a trade like this actually happen?

Let’s break it down like this:

• Tyler Biggs: 
  • 0 NHL Games Played
  • 0 career goals, 0 career points
  • Fun Fact: Scored a career-high 18 goals in the East Coast Hockey League and at 27-years-old doesn’t play professional hockey anymore
• John Gibson:
  • 287 NHL Games Started
  • 2.53 GAA, 0.918 Sv %, 139-103- 33 record
  • Fun Fact: 2015-16 William Jennings Trophy winner
• Rickard Rakell
  • 447 NHL Games Played
  • 129 Goals, 283 Points
  • Fun Fact: Two-Time 30 Goal Scorer

Do I really need to say anything else? When you move two draft picks for one, you better select a great player. Instead, the team moved on from a 30-goal scorer and starting NHL goalie for a nobody.

I know this is third-worst on this list, but in 10 years, it could be number-one if Rakell and Gibson continue to have great NHL careers.

#2. The Infamous Rask for Raycroft Deal

The Trade:

• Toronto Maple Leafs acquire: Andrew Raycroft
• Boston Bruins acquire: Tuukka Rask

Every NHL fan knows this trade and if you’re a Toronto Maple Leafs supporter, it still haunts you to this day.

Two years prior to making this trade, Andrew Raycroft had won the Calder Trophy as the NHL’s rookie of the year. It’s a great accomplishment, but if the Boston Bruins were willing to ship him away for an unknown goaltender from Finland, isn’t that fishy? If you’re the GM of the Toronto Maple Leafs at the time, aren’t you like, “Well that was easy?”

The Boston Bruins had Tim Thomas ready to become the starter, so they gave Andrew Raycroft the opportunity for more playing time in Toronto, but shipping away a 25-year-old goalie isn’t a decision that most teams do. It’s almost like they knew what they were doing, while the Toronto Maple Leafs had no friggin’ clue!

Oh wait, that’s exactly what happened.

I’ll paint the picture lightly, but things did not go well in Toronto for Raycroft. In fact, he only played two seasons, averaging a save percentage much lower than .900%. While Raycroft was stinking it up in Toronto, the Boston Bruins were patiently waiting for Tuukka Rask to develop into their future number-one goaltender.

Before they knew it, the Finnish superstar would win the Vezina Trophy and become one of the best goaltenders in the NHL. The Toronto Maple Leafs had two star goaltending prospects at the time and chose the wrong one to keep. Justin Pogge was the other goalie and he did even worse than Raycroft, as he only played seven career NHL games.

This is a trade that still hurts, as Rask could have been the goalie for the past decade for the Toronto Maple Leafs, but instead, he beats the Leafs every spring.

#1. Leafs Give Away Chance at One of NHL’s Best Defenseman

The Trade:

• Toronto Maple Leafs acquire: Tom Kurvers
• New Jersey Devils acquire: 1991 1st Round Pick (Scott Niedermayer)

When you have an opportunity to trade for Tom Kurvers, you have to do it. No matter what the package is in return.

I’m joking, obviously.

Kurvers was an offensive defenseman who the Toronto Maple Leafs thought could help their blue-line. What they didn’t know at the time was that there was a defenseman already sitting there waiting for them, in the 1991 NHL Entry Draft, instead.

Unfortunately, Toronto got excited and traded their 1991 first round pick away to the New Jersey Devils. The Toronto Maple Leafs thought they would be a much better team during the 1990-91 season because that first-round pick they gave up, turned into the third-overall selection.

And with the third-overall pick in the 1991 NHL Entry Draft, the New Jersey Devils were proud to select, from the Western Hockey League: “Scott Niedermayer.”

Niedermayer only went onto to win one Norris Trophy and one Conn Smyhe Trophy, but besides that he wasn’t that good….Sorry that’s the regretful Leafs fan in me talking. He was one of the most beautiful skaters in the history of the NHL and finished his career with 740 points in 1263 games, while capturing four Stanley Cups.

Niedermayer stepped into the NHL immediately and was an impact player in every game he ever played, and would have been an amazing piece for the Toronto Maple Leafs.