It's hard enough that the Boston Bruins beat the Toronto Maple Leafs in seven games every time they play each other, but do they have to steal their prospects away too?
The Leafs farm system has been thin since their glory days run from 2015-2019 where they developed future NHLers like Zach Hyman, Connor Brown, Kasperi Kapanen, William Nylander, Justin Holl, Mason Marchment, Timothy Liljegren, Trevor Moore, Rasmus Sandin and others. That run was magical as the Toronto Marlies were sometimes more exciting than their big club, as they made multiple conference championships, including winning a Calder Cup.
Say what you want about Kyle Dubas, but he did a fantastic job developing future NHL talent and although he traded some of it away, it wasn't because they were bad players. Instead, he either traded or let them go in free agency because they got too expensive. In a salary-cap world, you can't sign everyone and based on how he developed players before, I assume he thought he could keep replacing the cuppboard with cheap talent.
Unfortuantely Dubas never got that opportunity as he was fired, and current GM Brad Treliving seemingly doesn't care much about the farm system, as there haven't been many Marlies graduates. The only player who is making a decent impact is Nick Robertson, but I think we all wish he had more production and a bigger opportunity, despite his recent success.
The Boston Bruins recently re-signed Alex Steeves to an extension, making me reminisce on how bad they've continued to steal good young players from the Leafs. It's bad enough that the team has lost to the Bruins four times in the playoffs since 2014, but continuing to take our players is so frurstating.
With the recent Steeves signing, here are five players the Bruins have stolen in the past two decades
No. 1: Alex Steeves
Starting with Steeves, the team signed him as a college free agent in 2021 but he only played in 14 NHL games between then and 2025. Despite becoming the Marlies franchise leader in goals and points, the Leafs never gave him a true opportunity and he's now become a steady third-line centre on the Bruins alongside this next player...
No. 2: Fraser Minten
The Leafs traded a fourth round pick and conditional fifth round pick, alongside Minten to the Bruins for defenseman Brandon Carlo. As much as I can understand trading away a high-end prospect in order to acquire a top-four defenseman, this trade always bothered me.
Minten essentially looked like a future Scott Laughton, so trading another first-round pick for Laughton never made sense, and that's currently coming true. Minten has played mostly on the wing this year but he'll eventually translate to a NHL centre. In 50 games, he has 12 goals and could have been a cheap fourth-liner instead of Calle Jarnkrok this year.
No. 3: Dougie Hamilton & No. 4: Tyler Seguin
We're looping these two together because it was the same trade. Back in 2009, the Leafs thought they needed a goal-scoring winger to get over the hump, so they traded away two first-rounders for Phil Kessel. That plan immediately backfired, as Toronto's record plumetted, resulting in them giving away the No. 2 and No. 9 overall picks in back-to-back drafts.
The Leafs could have had a decade of Tyler Seguin and Dougie Hamilton, but instead recieved Phil Kessel and Tyler Biggs, who was a bust. Both Seguin and Hamilton are local kids too, so they would have shined in the Toronto spotlight, but instead went onto have great careers elsewhere.
No. 5: Tuuka Rask
This may be the worst sentence in Leafs history: "The Toronto Maple Leafs have traded the rights to Tuuka Rask to the Boston Bruins in exchange of Andrew Raycroft." Depsite drafting Rask with a first-round pick in the 2005 NHL Entry Draft, GM John Ferguson Jr. decided to trade him to the Bruins for the recent Calder Trophy winning goalie Andrew Raycroft.
Raycroft was a fine goalie, but he only played two seasons in Toronto, while Rask had a stellar 15-year career with the Bruins, winning a Vezina Trophy in 2014. He also won a Stanley Cup as a back-up goalie to Tim Thomas in 2011 with the organization and was one of the most consistent goalies in the NHL from 2010-2022.
After having Curtis Joseph and Ed Belfour, the Leafs could have had Rask for the next 15 years to solidify their goaltending, but instead it's been very inconsistent with a revolving doors of netminders. This is hands down the worst trade in the 21st century of Leafs history and incredibly frustrating that it happened with Boston.