Skip to main content
Come Fan with UsSunday, June 28, 2026

Bruins vs. Maple Leafs: Phil Kessel trade revisited in first-round series

The Bruins and Maple Leafs Eastern Conference Quarterfinal series will mark the first postseason meeting of Phil Kessel and Tyler Seguin since Toronto acquired Kessel in 2009.

Bob DeChiara-USA TODAY Sports

While it might not be entirely fair, Phil Kessel and Tyler Seguin will likely be compared for the entirety of their time with the Boston Bruins and Toronto Maple Leafs.

Kessel was acquired by Toronto from Boston for a 2010 first-round pick, which turned into Seguin. For the first time since the trade, the two will meet in a playoff series later this week.

In previous meetings between the Northeast Division rivals, the Boston crowd at TD Garden chanted "Thank You, Kessel," as the trade not only afforded the Bruins Seguin but also resulted in the drafting of highly touted defenseman Dougie Hamilton.

Seguin recently stated he pays no mind to the situation, while Kessel hasn’t spoken to the media for some time (Toronto general manager Dave Nonis says that will be changing, though).

However, others will certainly be talking about the scenario and will be revisiting what could have been had the Maple Leafs decided to hold onto those picks. This will especially be true depending upon the amount of production the two players provide.

Of course, the story line might just be a manufactured component to a series featuring two division rivals, one of which hasn’t made a postseason appearance in almost a decade. While it might have little consequence on the outcome, it is an interesting component to the series. Certainly, hindsight will be clear as day in the event one player (namely, Seguin) makes a huge impact on the outcome.

Regardless, the trade wasn’t the idea of the players and was a result of a management decision. Unfortunately, the players are the ones who will be pressed to address it and more likely than not, it will come up at some point.

More in the NHL:

Complete Stanley Cup Playoffs coverage

Bet on these hot playoff teams

A day in the life of an off-ice official

The best of our hockey network

See More: