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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Owen Nolan, Toronto Maple Leafs
Owen Nolan, Toronto Maple Leafs (Photo By Dave Sandford/Getty Images/NHLI) /

Leafs Trade for Owen Nolan (2003)

The Toronto Maple Leafs are a competitive team pushing for a playoff run. Sundin and Alexander Mogilny are leading the way, with Ed Belfour playing great in net. Head coach and general manager Pat Quinn wanted to bolster the team’s forward group. He chose to look at the failing San Jose Sharks and traded for power forward Owen Nolan.

Heading to California was Alyn McCauley, Brad Boyes, and a first-round pick. With the first-rounder, San Jose drafted defenseman Mark Stuart. In trading for Nolan, Toronto gets a big body forward to protect superstars Mogilny and Sundin while being a secondary scorer. He was the perfect addition to take the Leafs through a deep playoff run.

Nolan played very well in a Maple Leafs sweater. He picked up 12 points in 14 games following the trade and two points in seven games during the playoffs. That was followed up with 48 points in 65 regular-season games the season after.

The forward had a hard time staying on the ice due to injuries and even missed the playoffs in his second season with Toronto. After that, he took a season off from hockey after the lockout year before signing with the Pheonix Coyotes.

Boyes ended up becoming a 40-goal scorer and was a reliable secondary scorer for most of his career. He became a center the Leafs sure would have loved to have.  McCauley didn’t play in the NHL much longer after leaving Toronto. In his time with the Sharks, he was a solid third-liner that was more than reliable defensively.

The first-round pick was from the 2003 NHL Draft. That ended up being one of the deepest drafts ever, producing Eric Staal, Ryan Getzlaf, and Patrice Bergeron. Toronto would have had the opportunity to draft Bergeron, Corey Perry, or Ryan Kessler with that first-rounder.

Had Nolan stayed with Toronto and remained healthy, the deal would not have been that bad. Unfortunately, that did not end up happening. What “could have been” heavily outweighed what happened. The result of that is one of the worst trades the Leafs have ever made.