Toronto Maple Leafs: Top 3 most foolish trades they ever made

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Bernie Parent (Photo by Jim McIsaac/Getty Images) /

The Toronto Maple Leafs have made many foolish trades over the years. Which three stand out as the worst?

As an Original Six team, the Toronto Maple Leafs have a lot of history. Only the Montreal Canadiens have won more Stanley Cups than them. However, their history since 1967, the last time they won the Stanley Cup, has been painful at best.

Since 1967, the Leafs haven’t been defined by Stanley Cups, as they were in the pre-expansion era. Rather, they’ve been defined by their failures, both on and off the ice. The Leafs currently have the longest Stanley Cup drought of any NHL franchise. Even the Carolina Hurricanes managed to stumble upon a Stanley Cup. The Leafs haven’t.

This is largely because the Maple Leafs have made some pretty awful trades in the expansion era. But which ones stand out as the worst ones? Let’s set some guidelines. First of all, which ones are the most obvious ones the Leafs have lost? Secondly, which ones had a foolish result? Thirdly, which ones sum up why the Leafs haven’t won a Stanley Cup since 1967?

With all of these factors in mind, let’s look at the three worst trades in Maple Leafs history.

3. Leafs Trade Bernie Parent To The Flyers

In 1973, the Toronto Maple Leafs made a seemingly harmless trade. They moved goaltender Bernie Parent to the Philadelphia Flyers after he requested a trade. In return, the Leafs got Bob Neely and Doug Favell. Not bad for someone who had no desire to play for the Leafs, right?

Wrong. Parent went on to lead the Flyers to back-to-back Stanley Cups in 1974 and 1975. He won the Conn Smythe Trophy and Vezina Trophy in both seasons. In 1974, Parent nearly completed the Triple Crown by also winning the Hart Trophy, but lost to Phil Esposito by 35 votes.

Parent was actually pretty good for the Maple Leafs. He just had no desire to play for them after his stint in the WHA didn’t work out for him. Considering how well Parent played for the Flyers, they got a horrible return for him. Neely had 89 points in over 250 games for the Leafs while Favell posted a 26-26-16 record for the Leafs.

Tuukka Rask, Boston Bruins (Photo by Claus Andersen/Getty Images) /

2. Leafs Gift Bruins A Franchise Goalie

Yeah, the Toronto Maple Leafs really don’t have a good history when it comes to trading goalies. Though Tuukka Rask isn’t a Hall of Famer (yet), this one stings even more than the Parent trade because this one was completely unnecessary. At least Parent demanded a trade. Rask didn’t.

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The Leafs drafted Rask back in 2005, making him the 21st overall selection in the first round. Rask had a great first post-draft season, posting a .926% save percentage in 30 games in Liiga, which is Finland’s top professional league.

However, in the summer of 2006, the Leafs decided to trade Rask to the Boston Bruins for Andrew Raycroft. Why? Because they felt Justin Pogge was their goalie of the future. Pogge only played in seven NHL games, so the Leafs were quite clearly wrong.

Another reason this trade was horrible is because the Bruins were reportedly going to release Raycroft anyway. So the Leafs could have gotten him for free without giving up a top goaltending prospect. Plus, according to Steve Simmons, the Bruins actually preferred Pogge.

Rask has haunted the Toronto Maple Leafs since the trade. He has stopped them numerous times in the postseason. Against the Leafs during the regular season, Rask has a 19-7-2 record with a .926% save percentage.

Scott Niedermayer, New Jersey Devils (Photo by Bruce Bennett/Getty Images) /

1. Maple Leafs Help Build A Dynasty… For The New Jersey Devils

The New Jersey Devils had a quasi-dynasty in the mid-1990s to early 2000s. They won three Stanley Cups during that span in 1995, 2000, and 2003. The Devils got a bit lucky because they were basically handed the dynasty in a series of moves.

In 1990, the Calgary Flames helped by trading up in the 1990 draft to pick Trevor Kidd over some dude named Martin Brodeur. All Brodeur did was become one of the best goalies in NHL history. Then there’s the whole Scott Stevens offer sheet fiasco. But the Toronto Maple Leafs helped them as well by trading them the draft pick that wound up being defenseman Scott Niedermayer.

Back in the 1980’s and early 1990’s, the Maple Leafs enjoyed setting first round picks on fire, as they’d trade one at the blink of an eye. They were struggling at the start of the 1989-90 season, so they wanted to make a big move.

However, the Leafs also didn’t want to give up their 1990 first-round pick because they were bad. So they traded their 1991 first-round pick for New Jersey Devils defenseman Tom Kurvers. Initially, the trade looked good, as Kurvers helped the Leafs turn around their season and make the Stanley Cup Playoffs.

And then everything went downhill. The 1991 draft, for those who didn’t know, was considered to be a great one thanks to Eric Lindros, who was putting up eye-popping numbers in junior hockey. Unfortunately, injuries make him a popular “what if he stayed healthy?” discussion, but when Lindros was healthy, he justified his hype.

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Anyway, the Leafs started the 1990-91 season horribly with a 1-9-1 record. Though Toronto didn’t wind up with the worst overall record, they did wind up with the second-worst record. Thanks to the San Jose Sharks entering the league, the Devils had the Leafs first-round pick in 1991, which they used to draft Scott Niedermayer.

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