Boston Bruins
Ranking the Maple Leafs’ Worst Deals With the Bruins
Dive into the history of Boston and Toronto trades. Learn why some believe the Leafs should avoid trading with the Bruins moving forward.
In a recent episode of Leafs Morning Take, hosts Nick Alberga, Jay Rosehill, and guest Mike Grinnell revisited the trade that saw the Toronto Maple Leafs send Fraser Minten to the Boston Bruins. Given that the Bruins were playing Toronto on Tuesday night, the conversation about what is the disaster of a trade that deal turned into has been front-page news.
Toronto won the battle on Tuesday night. However, many will argue that Boston won the war — at least when it comes to trades between the two organizations.
Lightheartedly, but also somewhat seriously, Alberga argued that the Leafs should never be able to trade with the Bruins again. Why? Because their past history of past deals has rarely, if ever, favored the Maple Leafs. The segment quickly broke down three infamous trades that still sting in Toronto.
Here’s a ranking of the worst Bruins–Maple Leafs trades from Toronto’s perspective, based on long-term impact:
Tuukka Rask for Andrew Raycroft (June 2006)
Toronto traded its 2005 first-round pick — used on Tuukka Rask — straight up for veteran goaltender Andrew Raycroft. Rask went on to become a Bruins franchise cornerstone: a Vezina Trophy winner, Stanley Cup champion, and one of the most reliable netminders of his era.
Raycroft delivered two mediocre seasons in Toronto before being flipped. Two decades later, this deal remains one of the most lopsided in modern NHL history and a constant reminder of what could have been in goal for the Leafs.
Phil Kessel Trade (September 2009)
Boston sent the high-scoring winger to Toronto in exchange for three draft picks: first-rounders in 2010 and 2011, plus a 2010 second-rounder. Kessel was a good player for the Maple Leafs. However, the Bruins turned those selections into Tyler Seguin (No. 2 overall), Dougie Hamilton (top-10 pick), and Jared Knight.
To be fair, Boston didn’t get the most out of this deal either. They jumped the gun on both Seguin and Hamilton, trading them before they became solid and consistent pieces with other franchises. However, Seguin was part of Boston’s 2011 Stanley Cup team, and Hamilton had three productive seasons before moving on to the Calgary Flames. Kessel was eventually traded away.
Fraser Minten + 2026 1st (top-5 protected) + 2025 4th for Brandon Carlo (March 2025)
This is the deal that sparked the conversation and still feels fresh.
Toronto shipped out top prospect Fraser Minten, a high draft pick, and a fourth-rounder for veteran shutdown defenseman Brandon Carlo. In 2025-26, Minten has already emerged as a top-six center for the Bruins, posting 16 goals and 31 points through 70 games with strong underlying numbers and a +22 rating. Carlo has been let down on Toronto’s blue line (0 goals, 7 assists in 49 games), and was heavily discussed in trade conversations at this season’s deadline.
Toronto has traded young talent and future assets for immediate NHL help, only for Boston to develop or extract maximum value from what they receive. As the clip’s hosts concluded with classic rivalry frustration — “Let’s not do that anymore.”
It’s no wonder Maple Leafs fans are bitter. History shows that when the Bruins and Maple Leafs make a trade, one side usually gets the better deal. And, it’s not Toronto.
Next: Friends No More: Cowan and Minten Get Personal
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