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Penguins Trade Masterclass Highlighted by Analysts as One of the Most Embarrassing Leafs Moves of the Decade


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Jack Sutherland
September 3, 2025  (4:53 PM)
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Penguins forward Phil Kessel
Photo credit: Back Sports Page

Analysts have described the Toronto Maple Leafs trading of forward Phil Kessel to the Pittsburgh Penguins as one of the worst blunders Toronto has committed, especially after winning 2 Stanley Cups.

Former Toronto Maple Leafs forward Phil Kessel escaped the media fish bowl of intense scrutiny that was the Toronto hockey media market when he was traded to the Pittsburgh Penguins in 2015.
It turned out to be one of the best moves that the Penguins ever made, as Kessel helped them win back to back Stanley Cups in 2016 and 2017.

How Kessel Sparked Pittsburgh's Championship Run

Per analyst Ben Fisher of Hockey Writers, the Kessel-to-Toronto trade was one of the most embarrassing moves the Leafs have made in the last decade.
This trade looks especially paltry when you consider how Kessel fared in the aftermath. The speedy, high-scoring winger was the Penguins' missing piece alongside Sidney Crosby and Evgeni Malkin, helping deliver back-to-back Stanley Cups as soon as he arrived in Pittsburgh. He even enjoyed a renaissance 2017-18 campaign, with 34 goals and a career-best 92 points.

The Maple Leafs have been in the playoffs every year since 2017, but they've only won a pair of series, meaning they've still only won 2 playoff series since 2004.

Toronto's Return Fizzled While Kessel Thrived

In return for Kessel, the Maple Leafs got a pair of draft picks along with Kaspari Kapanen, Scott Harrington and Nick Spaling.
Neither Harrington or Spaling made any considerable impact with the Leafs, while one of the draft picks was later traded to acquire goalie Frederik Andersen. Andersen had a positive tenure with the Leafs, but never won a postseason series, which included consecutive Game 7 losses to the divisional foe Boston Bruins.
Kapanen had a decent time in Toronto, but never made a major impact.
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Penguins Trade Masterclass Highlighted by Analysts as One of the Most Embarrassing Leafs Moves of the Decade

Did the Maple Leafs make a terrible mistake by trading Phil Kessel to the Penguins?

Yes2080 %
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