Five Worst Maple Leafs Trades Of The Salary Cap Era

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Feb 12, 2015; Tampa, FL, USA; Tampa Bay Lightning defenseman Anton Stralman (6) and St. Louis Blues left wing Alexander Steen (20) skate after the puck during the first period at Amalie Arena. Mandatory Credit: Kim Klement-USA TODAY Sports

The Toronto Maple Leafs, like all teams, have had their share of transaction blunders. Let’s take a look at the worst five trades the blue and white have made since the inception of the salary cap.

The top five Maple Leafs transaction follies span just over three years and involve three different General Managers: John Ferguson Jr., Cliff Fletcher and Brian Burke.

The salary cap era hasn’t been kind to the Toronto Maple Leafs in any way but these deals have proven to be particularly painful when you look at what the departing players have done since they were traded and who the draft picks turned out to be.

There will be more trades, presumably some before the current season ends, but we can only hope that Dave Nonis doesn’t make the same mistakes that his predecessors have made.

Note: If you’re looking for the Phil Kessel trade, move along. Kessel is a point a game player that scores 35 goals without a top NHL center. He’s basically a superstar all by himself.

Let’s get at it.

Next: #5: Alexander Steen

Jan 29, 2015; St. Louis, MO, USA; Nashville Predators goalie Carter Hutton (30) blocks the shot of St. Louis Blues left wing Alexander Steen (20) during the shoot out at Scottrade Center. The St. Louis Blues defeat the Nashville Predators 5-4 in a shoot out at Scottrade Center. Mandatory Credit: Jasen Vinlove-USA TODAY Sports

November 24, 2008 – GM Cliff Fletcher

Since being traded to St. Louis, Alex Steen has had two 20 goal seasons and a 30 goal season while amassing 250 points in 370 games and becoming a big part of the Blues offense.

Lee Stempniak had 61 points in 123 games during the two seasons that he played with the Maple Leafs.

This trade was a classic case of the Leafs giving up on a player too soon. Steen has found his way in St. Louis and the Blues couldn’t be happier with the deal as Stempniak is on his 5th team (NYR) since leaving St. Louis.

Next: #4: Brandon Saad

Jan 9, 2015; Edmonton, Alberta, CAN; Chicago Blackhawks forward Brandon Saad (20) scores a first period goal against the Edmonton Oilers at Rexall Place. Mandatory Credit: Perry Nelson-USA TODAY Sports

September 5, 2009 – GM Brian Burke

The Maple Leafs dealt away the pick that would turn into Brandon Saad in this deal. Saad had 19 goals and 28 assists for 47 points last year for Chicago and is off to another good season with 12 points through the first 18 games this year.

Saad was part of the depth group that led Chicago to a Stanley Cup in 2013.

The pick that Toronto acquired would be included in the trade that brought Phil Kessel to Toronto, with Jared Knight being drafted by the Boston Bruins.

Next: #3: Roman Josi

Mar 23, 2014; Chicago, IL, USA; Nashville Predators defenseman Roman Josi (59) shoots the puck against the Chicago Blackhawks during the second period at the United Center. Mandatory Credit: Rob Grabowski-USA TODAY Sports

February 27, 2007 – GM John Ferguson Jr

With the current defensive woes of the Toronto Maple Leafs it’s hard not to be a little saddened over this trade.

Roman Josi has developed into a solid defenseman in Nashville and is fresh off a 13 goal, 27 assist season for the Predators. This year, Josi is on a similar pace after 18 games.

This was the second time that Yannic Perreault played for the Toronto Maple Leafs and it was no where near as successful as the first go-around. Perreault recored 5 points in only 17 games for Toronto after recording 33 points in 49 games in Phoenix before the trade.

Next: #2: Anton Stralman

Oct 9, 2014; Tampa, FL, USA; Tampa Bay Lightning defenseman Anton Stralman (6) and Tampa Bay Lightning center Brian Boyle (11) go after the loose puck during the third period at Tampa Bay Times Forum. Tampa Bay Lightning defeated the Florida Panthers 3-2 in overtime. Mandatory Credit: Kim Klement-USA TODAY Sports

July 27, 2009 – GM Brian Burke

Anton Stralman has become one of the better possession defensemen around the entire NHL. Does that sound like something the Leafs would be interested in right now?

Absolutely.

This is another case of the Leafs giving up on a player too soon and having to watch his game grow and develop into something they would love to have.

Wayne Primeau had 8 points in 59 games with Toronto before he called it a career. This trade could have looked better had the Leafs not dealt the Brandan Saad pick to Chicago in the #4 trade on this list.

Next: #1: Tuukka Rask

Mar 22, 2015; Tampa, FL, USA;Boston Bruins goalie Tuukka Rask (40) against the Tampa Bay Lightning during the second period at Amalie Arena. Mandatory Credit: Kim Klement-USA TODAY Sports

June 24, 2006 – GM John Ferguson Jr

This, perhaps, will be the worst trade in modern Leafs history for a very long time. Everyone knows this story and the shame that comes with it.

Toronto has had to watch Tuuka Rask become one of the best goaltenders in the entire world and win a Stanley Cup with the Bruins in 2011.

Andrew Raycroft turned out to be a major bust that the Bruins couldn’t be happier to have washed their hands clean of. The biggest issue with this trade for me is that Raycroft turned in horrible numbers over thirty games the season prior to the trade. He had already turned into a bust before the Leafs traded away Rask for him.

In summary, the Leafs have made some pretty bad decisions over the years but in the salary cap era they’ve dealt away (essentially) Tuukka Rask, Brandon Saad, Roman Josi, Anton Stralman and Alex Steen.

Here’s hoping that this list remains in-tact, and no trades surpass them, for a very long time.

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