Toronto Maple Leafs: 5 Worst Free Agent Signings Of The Past Decade

TORONTO, CANADA - MARCH 29: Colby Armstrong #9 of the Toronto Maple Leafs skates with Wayne Simmonds #17 of the Philadelphia Flyers during NHL game action March 29, 2012 at the Air Canada Centre in Toronto, Ontario, Canada. (Photo by Graig Abel/NHLI via Getty Images)
TORONTO, CANADA - MARCH 29: Colby Armstrong #9 of the Toronto Maple Leafs skates with Wayne Simmonds #17 of the Philadelphia Flyers during NHL game action March 29, 2012 at the Air Canada Centre in Toronto, Ontario, Canada. (Photo by Graig Abel/NHLI via Getty Images) /
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Photo by Steve Russell/Toronto Star via Getty Images /

5. Jason Blake

Coming off a career year, where Jason Blake scored 40 goals with the New York Islanders, he was set for a big raise. The 5-foot-10 wing had a previous high of 28 goals in the 2005-06 season. Based on his production the last few seasons on Long Island, his cap hit of $4 million wasn’t bad. However, the Leafs made it worse by giving the 33-year-old wing five years of term. It wasn’t smart.

That’s why free agency is such a dangerous game. Teams get in bidding wars over players, so in order to get a player to sign, they have to keep adding more years or money. Anytime a player has his best season in a contract year, it should give interested teams pause. It happens time and time again. A player has a career year in his UFA season to cash in and then never replicates those numbers again.

Blake’s first six seasons in the NHL, from 2000-01 to 2006-07, his career earnings were $5.466 million. So his eyes must have lit up like a Christmas tree when he heard what the Leafs were offering.

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His numbers in his first two seasons in the blue and white were actually pretty respectable. 52 points in 82 games in year one, followed by 63 points in 78 games, is solid production on what was a bad team. What makes Blake’s first season so impressive is that he announced he was battling Leukemia. Battling the way he did made him an easy guy to root for.

Year three is where his production took a major dip. Just 26 points in 56 games, in what turned out to be his last season in Toronto. Blake, along with Vesa Toskala, was traded to Anaheim in exchange for Jean-Sebastien Giguere. Term is always the killer.

If that had been a short term deal, which it should have been, it would have been a good deal. Paying an undersized player through his mid-to late thirties was a recipe for disaster.