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Top 10 Worst Trades Made By The Toronto Maple Leafs

It's been 48 long years since fans have seen the Toronto Maple Leafs bring home the Stanley Cup. In those 48 years, the Leafs have missed the playoffs 20 times. So, it's probably safe to say that the franchise has made some mistakes over the last five decades and that, in part, the team's front office is to blame. From John Ferguson to Dave Nonis, not many general managers have had success in Toronto.

That lack of success has all led to this season, one of their worst performances in franchise history. The Leafs are finally looking to re-build their team the right way. But it hasn’t always been that way. In the past, and particularly over the last decade, the Leafs have opted to build their team through trades rather than in the draft.

In failed attempts to speed up the re-building process, the Leafs have given up on young players, dealt draft picks and undersold future assets to bring in unproven or washed-up veterans, while other trades were simply due to poor scouting reports or lack thereof. In order to put together a real contender in this league, you need patience. From fans to front office, the franchise has to be willing to wait and develop with its young players rather than forging a team together. Just look at the Chicago Blackhawks for example. Jonathan Toews and Patrick Kane were drafted in 2006 and 2007. The Blackhawks didn’t trade them to bring in veterans; they simply waited and built a winning team around their young talent. Maybe the Leafs could take a lesson or two.

So, without further adieu, let’s analyze some of the worst deals made by the Leafs.

10 10. Doug Gilmour, Dave Ellett and a 1999 third-round pick for Jason Smith and Steve Sullivan

via kiss925.com

Despite playing only six seasons with the Leafs, Doug Gilmour is remembered as one of the most famous players in franchise history. Gilmour never won a Stanley Cup with the Leafs but he came close in his second and third seasons with the team.

9 9. Joe Colborne for a 2014 fourth-round pick

Nick Turchiaro-USA TODAY Sports

The Leafs have a bad tendency of giving up on young players and Joe Colborne was one of them when he was traded to the Calgary Flames for a conditional fourth-round pick. Despite failing to crack the Leafs NHL roster three seasons in a row, the 23-year-old centre stood at six-foot-five and over 200 pounds.

8 8. Jiri Tlusty for the rights to Philippe Paradis

Anne-Marie Sorvin-USA TODAY Sports

Jiri Tlusty was another player given up on by the Leafs, as he was traded to the Carolina Hurricanes in return for the rights to Philippe Paradis. You don’t remember Philippe Paradis? That’s because he never played an NHL game.

Tlusty only managed to record only 20 points over 74 games in three seasons with the Leafs but went to become a solid second-line centre with the Hurricanes. Granted, Tlusty only produced two 35-piont-seasons in Carolina but the Leafs practically gave him away for nothing.

7 7. 2013 second-round pick, 2013 fourth-round pick and 2014 fourth-round pick for Dave Bolland

John E. Sokolowski-USA TODAY Sports

Instead of holding onto draft picks and preparing for the future, the Leafs dealt some picks to the Chicago Blackhawks in return for Dave Bolland back in 2013/14.

Had Bolland been healthy during his season in Toronto, this may have been a decent trade for the Leafs. However, Bolland played only 23 games in a Leafs jersey scoring 12 points. Then, after one season, the Leafs lost Bolland to free agency.

6 6. 2011 first-round pick (Rickard Rakell) and a 2011 second-round pick (John Gibson) for 2011 first-round pick (Tyler Biggs)

Kirby Lee-USA TODAY Sports

In this trade with the Anaheim Ducks, the Leafs gave up their first and second round draft picks in order to get a higher pick in the first round in the 2011 NHL entry draft.

The Ducks used their acquired picks to draft forward Rickard Rakell 30th overall and goalie John Gibson 39th overall. In his third season with the Ducks, Rakell notched 31 points in 71 games this year and looks set for a bigger role in the future. Gibson, one of the league’s best young goalies, won 13 of 21 starts this seasons.

5 5. Darryl Sittler for Rich Costello, Peter Ihnacak and Ken Strong

via grhosp.on.ca

At the time, Darryl Sittler was the Leafs captain and leading scorer in franchise history with 916 points. Apparently this wasn’t reason enough keep him around. Sittler never hoisted the Stanley Cup with Toronto but he was consistently their best player through hard times and bad seasons with the franchise.

4 4. Alex Steen and Carlo Colaiacovo for Lee Stempniak

Jasen Vinlove-USA TODAY Sports

In 2001, the Toronto Maple Leafs drafted Carlo Colaiacovo 17th overall and one year later, they drafted Alex Steen 24th overall. In 2008, the Leafs traded Colaiacovo and Steen to the St. Louis Blues for Lee Stempniak.

The Blues drafted Stempniak 148th overall in the fifth round in 2003. Steen and Colaiacovo scored a combined 159 points over their tenures in Toronto. Meanwhile, Stempniak recorded 130 points for the Blues.

3 T2. Scott Niedermayer for Tom Kurvers

via hfboards.hockeysfuture.com

In 1989, the Leafs traded their first-round pick in the 1991 NHL entry draft to the New Jersey Devils for defenseman Tom Kurvers. Kurvers scored 55 points in 89 games during his time with the Leafs before they traded him to the Canucks.

2 T2. Phil Kessel for a first (Tyler Seguin) and second round pick (Jared Knight) in 2010 and a first-round pick (Dougie Hamilton) in 2011

via causewaycrowd.com

At the time, the Leafs seemed like the clear winner in this deal with the Boston Bruins. They acquired a 35-goal scorer and possible franchise player in Phil Kessel.

Now let's fast forward a few years. The first round pick from the Leafs became the second overall pick as they were horrendous in 2008/09 and the Bruins selected Tyler Seguin with that pick. With their second first rounder from the Leafs, the Bruins then took Dougie Hamilton in 2011.

1 1. Tuukka Rask for Andrew Raycroft

Kim Klement-USA TODAY Sports

This trade was just straight up bad, as it didn't involve draft picks like the Seguin or Niedermayer deals, that we're using hindsight to determine are bad. Tuukka Rask was already drafted and highly regarded by scouts, so he may be the biggest asset ever dealt by the Maple Leafs. Every team needs an elite goalie if they want to win and they don't come around all that often.

The Leafs needed a replacement for their former goalie, Ed Belfour. Meanwhile, Andrew Raycroft had just won the Calder Trophy in Boston, so at the time it seemed smart to trade for him.

Here is where the Leafs went wrong… In acquiring Raycroft, the Leafs had the choice to trade Rask or Justin Pogge and they chose to give up Rask, according to the Toronto Sun. So, the Leafs picked Raycroft and Pogge over Rask.

In 2014, Rask won the Vezina Trophy with the Bruins while Raycroft played only two seasons in Toronto. Pogge played seven games with the Leafs in the 2008-09 season, winning only one of them, and hasn’t played an NHL game since.

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Top 10 Worst Trades Made By The Toronto Maple Leafs