Top 5 Worst Signings In Toronto Maple Leafs History

MONTREAL, CANADA - MARCH 3: Mike Komisarek #8 of the Toronto Maple Leafs body checks Andreas Engqvist #63 of the Montreal Canadiens during the NHL game at the Bell Centre on March 3, 2012 in Montreal, Quebec, Canada. (Photo by Richard Wolowicz/Getty Images)
MONTREAL, CANADA - MARCH 3: Mike Komisarek #8 of the Toronto Maple Leafs body checks Andreas Engqvist #63 of the Montreal Canadiens during the NHL game at the Bell Centre on March 3, 2012 in Montreal, Quebec, Canada. (Photo by Richard Wolowicz/Getty Images) /
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TORONTO – NOVEMBER 30: Jason Blake #55 (Photo by Abelimages/Getty Images)
TORONTO – NOVEMBER 30: Jason Blake #55 (Photo by Abelimages/Getty Images) /

#5. Tim Connolly

Contract: Two-years worth $9 Million

After the departure of Mats Sundin in 2008, the Toronto Maple Leafs were on the hunt for a top-line center and hoped that Connolly would provide those services.

Maybe it was the hair-cut resemblance of Sundin that the Toronto Maple Leafs saw in Connolly, but this signing turned into a bust quickly.

During his two-year contract, Connolly only played one season with the Leafs, scoring 13 goals and 36 points, so he essentially was a $9 million per year player.

After his first year with the team, Connolly was demoted to the Marlies and played a total of 28 games with the Toronto’s farm system, where he ended his career.

#4. Jason Blake

Contract: Five-years worth $20 million

Blake was the definition of too good to be true when he signed with the Toronto Maple Leafs.

After coming off three consecutive 20-goal seasons, and then a 40-goal campaign with the New York Islanders, the Leafs thought they were acquiring a sniper.

However, in three seasons with Toronto, Blake scored a total of 45 goals in 216 games.

Blake was going through personal issues during his first season with the Toronto Maple Leafs having been diagnosed with chronic myelogenous leukemia, but he was still able to play a full season.

Blake’s second season in Toronto was much better as he scored 25 goals and 30 assists, but before he could finish his third season of a five-year contract, Blake was traded away to Anaheim for veteran Jean-Sebastien Giguere.