Jake DeBrusk always seems to show up when his Boston Bruins play their rival Toronto Maple Leafs — especially in the postseason. But with the 27-year-old set to become an unrestricted free agent on July 1, and rumblings that the front office won't offer the Canadian another contract in Beantown, the Leafs could be interested in bringing the power forward into the fold, according to the Toronto Star's Nick Kypreos.

“The Leafs continue to look at all options when it comes to their top six forwards next season,” the former player said in his latest column on Thursday. “There’s word they may have interest in pending Bruins free-agent Jake DeBrusk, who’s been a Leafs playoff killer over the years.”

DeBrusk scored 19 goals and 40 points over 80 games with the Bruins last season, a slight dip from his career-high 27 goals and 50 points in 2022-23. But he turned it on in the 2024 Stanley Cup Playoffs, amassing 11 points in 13 contests while helping Boston yet again beat Toronto in Round 1. It took until Game 7 overtime, but the Bruins remained perfect against the Leafs in their last seven postseason tries.

DeBrusk has moved around the top-six while in Massachusetts, but the left winger could fit in well as more of a middle-six option with the Leafs. It all depends on the price, though; DeBrusk made $4 million in each of the last two seasons, and will certainly be looking for an increase on the open market.

That's especially true with the salary cap going up, and considering the Leafs are already working on free agent deals for both Max Domi and Tyler Bertuzzi, who were solid in 2023-24 for the blue and white.

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Toronto Maple Leafs left wing Matthew Knies (23) and Boston Bruins right wing David Pastrnak (88) speak after the Bruins defeated the Leafs in overtime in game seven of the first round of the 2024 Stanley Cup Playoffs at TD Garden.
Bob DeChiara-USA TODAY Sports
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Make that seven consecutive postseason losses for the Leafs against the Bruins after they yet again bowed out in Round 1 of the Stanley Cup Playoffs in 2024. Boston firmly has Toronto's number come April, regardless of where the two Atlantic Division clubs finish in the regular-season.

Each of the last four have gone to Game 7, with Boston beating Toronto in 2013, 2018, 2019 and now 2024. Although none of that success culminated in a Stanley Cup for the Bruins, they advanced to the Final in both 2013 and 2019, losing to the Chicago Blackhawks and St. Louis Blues, respectively.

For the Leafs, the work continues to build a team that can figure out how to have lasting success once the regular-season concludes. And DeBrusk could be a good fit in that quest, although AFP Analytics projects him earning as much as $5.82 million AAV over five years.

With just under $20 million in cap space to work with — and still some other moves to make — it won't be easy to lock DeBrusk up in Toronto. But considering both his age and strong postseason contributions over the last few years, Toronto could be an attractive landing spot for the former Red Deer Rebel.

It will be intriguing to see where DeBrusk ends up on July 1, and whether it will be with the same team he has victimized come playoff time.