The 5 Worst Toronto Maple Leafs Trades or Signings Since 2000

Dave Nonis, Brian Burke, Toronto Maple Leafs (Photo by Bruce Bennett/Getty Images)
Dave Nonis, Brian Burke, Toronto Maple Leafs (Photo by Bruce Bennett/Getty Images) /
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Jeff Finger, Toronto Maple Leafs
Jeff Finger, Toronto Maple Leafs (Photo by G Fiume/Getty Images) /

With the trade deadline approaching, what are some Toronto Maple Leafs worst moves of the new century?

The Toronto Maple Leafs are one of the oldest and successful teams in the NHL. By successful, I mean before 1968. Anyway, not everything the team did went as planned.

Some moves looked horrid from the start, while other’s took time to reveal their negative consequences.

In honor of the upcoming trade deadline, let’s take a look at five of the worst moves the Leafs made since 2000.

Toronto Maple Leafs Sign Jeff Finger (2008)

The Leafs have a mediocre team with Hall of Famer Mats Sundin leading the way. Defenseman Thomas Kaberle is putting up more points than all but two forwards. Goaltenders Vesa Toskala and Andrew Raycroft played better on the bench than they did in the net.

Then general manager Cliff Fletcher knew he had to improve the team if the Leafs were to become competitive. To help improve the team, Fletcher looked to sign a defenseman.

Toronto couldn’t score, defend, or even hold onto the puck. To combat that, the Leafs signed defenseman Jeff Finger to a four-year contract worth $3.5 million per season.

Before arriving in Toronto, Finger played two seasons with the Colorado Avalanche. The team drafted him in the eighth round back in 1999. It took him six seasons until he played in his first NHL game. (stats from

Even then, the defenseman never saw the ice much. Finger played 92 games in two seasons, putting up 24 points, and was a plus 22. The argument for the signing was Finger’s defensive prowess and physicality. With the situation the Leafs were in, anyone was an upgrade. Finger looked like a decent risk to take, but not for a four-year contract.

In his new blue sweater, Finger looked like a different player, and not in a good way. He set a career-high with 23 points in 66 games one year into his new contract. The positives stop there. His inability to bring his defensive abilities to Toronto limited him to the 66 games. That would continue the following season as he played only 39 games before being waived.

From there, the defenseman played the rest of his two-year deal in the AHL and struggled to do that. He played in 23 games and 31 games, respectively.

The term “it can’t get any worse than this” was proven wrong by the Toronto Maple Leafs once again. It was a wasted signing that did not pan out at all. As bad as it sounds, it comes nowhere near the next horrifying move.