Jake DeBrusk is one of the most pressing question marks facing the Boston Bruins' front office this summer. Set to become an unrestricted free agent on July 1 — less than a week from now — there's a real chance the Canadian forward walks away if he isn't offered a suitable contract extension.

There have been rumblings that the Bruins will indeed let DeBrusk test free agency rather than make an attempt to re-up the 27-year-old. And he's already generating significant buzz this offseason, including from a team he has been especially potent against in the postseason. Toronto Star columnist Nick Kypreos reported that the Toronto Maple Leafs could be looking to sign the top-six winger.

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

Now, it looks like there could be mutual interest between DeBrusk and the Leafs, which adds even more credence to the rumor that he could be considering playing for the Atlantic Division rivals.

“I heard over the weekend that there’s actually mutual interest between the Leafs and Jake DeBrusk,” reported The Leafs Nation's Nick Alberga on Tuesday.

DeBrusk was solid in the 2023-24 regular-season for the Bruins, scoring 19 goals and 40 points over 80 games. It was a slight dip from a career year in 2022-23, where he found 27 goals and 50 points. But he turned it on in the 2024 Stanley Cup Playoffs, amassing 11 points in 13 contests and helping the Bruins yet again beat the Leafs in Round 1.

Boston does have over $23 million in cap space to work with, so there is certainly an avenue to get DeBrusk re-signed. But it's looking more and more likely that he'll finally move on after asking for a trade a couple of years ago.

But could he really go from the team he's spent his entire career with to one of their biggest Original Six rivals?

Leafs-Bruins rivalry remains one of best in league

The Toronto Maple Leafs and Boston Bruins shake hands 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

Dating back to 1969, Boston has beaten Toronto in each of the last seven postseason series between the two Atlantic Division rivals. Remarkably, the last four have all gone to Game 7.

And DeBrusk was on the Bruins' roster for three of those. He has scored in a Game 7 against the Leafs, and has helped the Americans continually come out on top against their northern neighbors.

Now, there's a chance he'll join them. And if he does, he'll likely be lining up with either Auston Matthews or John Tavares in 2024-25 — not a bad prospect for the two-time 27-goal scorer.

Projected to make as much as $5.82 million AAV over a five year contract (AFP Analytics), both the Leafs and the Bruins have the cap room to sign DeBrusk. But one thing is for certain: he will be commanding much more than the $4 million he made in each of the last two seasons on the open market.

It's going to be very interesting to see if DeBrusk will stay put in Massachusetts, head west to Ontario, or sign with a different franchise altogether for the long-term.