Articles / Maple Leafs’ 5 Worst Trades of the Past Decade

Maple Leafs’ 5 Worst Trades of the Past Decade

T
The Hockey Writers
Sep 3, 2025 6:00 PM

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The Toronto Maple Leafs have had their share of questionable trades over the past decade, often leaving fans scratching their heads. One of the most notorious trades was sending Phil Kessel to the Pittsburgh Penguins in 2015. While Kessel delivered two Stanley Cups to Pittsburgh, the return of draft picks and players has not yielded the hoped-for success for the Leafs, leaving a gaping hole in their roster.

Another deal that stands out is the 2016 trade that sent fan favorite, Jake Gardiner, to the Carolina Hurricanes. Gardiner was a vital part of the Leafs' defense, and trading him for futures didn’t quite fill the void in the lineup. In retrospect, the loss of his playmaking ability could have been pivotal in tight playoff situations.

One particularly head-scratching transaction was the trade of Nazem Kadri to the Colorado Avalanche. Kadri had developed into a resilient center, but after the trade, he flourished in Colorado, becoming a key player in their quest for the Cup. The return of a player in Alexander Kerfoot has not matched Kadri's impact, further accentuating the failure of that trade.

Additionally, the Maple Leafs' decision to trade for Tomas Kaberle during his later years proved to be a disappointment. Kaberle’s experience and playoff contributions were expected to elevate the team; however, he struggled to perform at the necessary level, and the returns from that trade did not meet fan expectations. These trades illustrate a broader pattern, where the team was unable to capitalize on its moves, resulting in a decade of missed opportunities and unfulfilled promise on the ice.

As the Maple Leafs continue to build towards a championship, learning from past mistakes will be crucial for the organization. Understanding the importance of making the right trades and maintaining a balanced roster could be the key for future success.