Worst Trades in Maple Leafs History:

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As we get closer to the NHL trade deadline on March 21st, we will look at the five worst trades that the Toronto Maple Leafs have made in their 105-year history. Today we will be talking about trade numbers five and four.

#5: It’s a ‘Biggs’ Deal 

One of Brian Burke’s finest trades, trading away the 1st and 2nd pick in that same draft for Tyler Biggs who went on to play a lot of ECHL and AHL games but never played in an NHL game.

The Package:

The Maple Leafs acquired the 22nd pick in the 2011 1st round, which they used to select power forward, Tyler Biggs. This trade was one that Brian Burke was in love with, he spoke highly of Biggs, and well nothing ever came of his career. His NHL stat line is 0 points in 0 games and an amazing 15 points in 108 AHL games. The most notable thing that Biggs was a part of during his time in the Leaf’s organization is the Phil Kessel trade to the Pittsburgh Penguins in 2015, which was the beginning of the rebuild that brought all the stars we love today. However, since 2018-19, Biggs hasn’t played hockey in an organized league and hasn’t been involved in the game in any capacity. 

The Return:

To get Tyler Biggs, Brian Burke traded the 30th, pick to the Anaheim Ducks which led to them drafting Rickard Rakell with the 30th pick. He has had an above-average NHL career collecting 329 points in 534 games, in his 10 years with the Ducks. With the 39th pick in that draft, they selected goaltender John Gibson, who would have solved a lot of issues that the Maple Leafs for years to come. Although it probably would have meant no Jack Campbell or Frederik Andersen, Gibson has been considered an elite goalie in the NHL for years. In his nine years with the Ducks, he has posted 162 wins, and 23 shutouts in 353 games, with a career, .917 SV% and a 2.58 GAA.

It is evident that this is one of the worst trades in Maple Leafs’ history but also in Brian Burke’s career. He thought that Biggs would bring great success to the organization, and in turn, trading those picks wouldn’t have mattered. However, it went the complete opposite way and hurt the team until recently, when they managed to complete a proper rebuild. Even if the Maple Leafs didn’t want to draft either Rakell or Gibson with those picks, there were options for them to draft rather than trading the 30th, and 39th picks to draft Biggs.

Here are a few of the options they missed out on:

#4:  Bobby Lu

Imagine Roberto Luongo wearing a Maple Leafs jersey? Well, it could have happened in 1997 but instead, on March 13th 1996, they bundled a package and sent it to the New York Islanders to bring back fan favourite Wendel Clark, defenceman, Mathieu Schneider, and D.J. Smith.

The Package:

Sean Haggerty was a draft pick by the Maple Leafs in 1994, in the 2nd round with the 48th pick. His time with the team was short only playing one game with them. He would go on to play only 14 games in the league amassing one goal and two assists.

Darby Hendrickson was a depth piece in the organization, drafted in the 4th round with the 73rd pick in the 1990 NHL draft. He played 233 games with the Maple Leafs, scoring 47 points before he was traded to the Vancouver Canucks on February 16th 1999. He would go on to play for the Minnesota Wild in 2000-01 where he would find his best success with 60 points in 182 games.

Kenny Jonsson was the second biggest piece of the trade, as he was the 12th overall pick by the Maple Leafs in the 1993 NHL draft. His time was short with the team, playing in only 89 games and collecting 35 points. After the trade out of town to the New York Islanders, he found success. Jonsson became a serviceable top 4 defenceman there, playing 9 seasons with them. During his time with the Islanders, he played in 597 games and scored 232 points.

When it comes to the 1st round pick in the 1997 NHL draft, many would argue that the Maple Leafs may not have had the choice to select Roberto Luongo due to their bad luck. Nevertheless, the pick that they traded ended up being the 4th overall selection and was used to draft future Hall of Famer, Luongo. Due to the scenario and the ‘what-ifs’ that come into play, it is hard to say he would have been the goalie he was by the end of his career. However, he was the 4th overall pick, and the only goalie picked in the top 20, so all indications point to him having a successful career. The other argument that some say is, what if he was picked before #4, well in that 1997 draft the top five were:

  1. Joe Thornton (Future Hall of Famer)
  2. Patrick Marleau (Future Hall of Famer)
  3. Olli Jokinen
  4. Roberto Luongo
  5. Eric Brewer

All these players drafted in the top five had success in the NHL and would have had an impact on the Maple Leafs during their primes (although four of the five did play for the team, it wasn’t during their primes). However, Luongo is one of the greatest goalies in his era, and that is something that the team had issues with for years after that draft.

The Return:

Bringing back Clark was a big move; he was loved by so many fans here; he would play the rest of the 1995-96 season; and a combined 112 games over the next two seasons before leaving to play with the Tampa Bay Lightning. He would later return one last time in 1999-00 where he played only 20 games.

Mathieu Schneider stayed with the Maple Leafs for just under three seasons as well. He played the duration of the 1995-96 season, in the next two seasons he played 102 games, highlighted by a 37-point season in 1997-98. On October 14th 1998, Schneider was traded to the New York Rangers for Alexander Karpovtsev and a 4th in 1999, which turned out to be Mirko Murovic.

D.J. Smith was with the Maple Leafs for years after the trade-in 1995. He did, however, spend most of his time in the AHL with the St. John’s Maple Leafs. He would go on to play for the Colorado Avalanche, and their minor league affiliate. D.J. Smith did come back to the organization as an assistant coach to Mike Babcock, he is currently the head coach of the Ottawa Senators.

Although Clark and Schneider stayed for just under three years, if you follow this trade tree it leads to Schneider to the Rangers for Karpovtsev and Clark walked to free agency for free, when it could have been Roberto Luongo for years. The other major piece to the trade was, Kenny Jonsson, who was hyped as an elite defence, with a similar style to Maple Leafs legend Borje Salming, and it didn’t show in his time with the team. Overall, this trade wasn’t the best one of GM Cliff Fletcher’s career and often leaves Maple Leafs fans wondering what could have been.

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