With Jake DeBrusk reportedly requesting a trade, what return could Bruins net? taken at BSJ Headquarters (Bruins)

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It sure looks like Jake DeBrusk’s time in Boston is coming to a close.

After getting scratched ahead of Boston’s win over the Canucks on Sunday night, it appears as though the relationship between the winger and the Bruins has reached its breaking point — with DeBrusk’s agent, Rick Valette, confirming to TSN’s Ryan Rishaug that a formal trade request was put in over the weekend.  

Sportsnet’s Elliotte Friedman noted that a trade wasn’t imminent, but the writing sure seems to be on the wall that a fresh start is needed for all parties at this point. 

Even though the 2021-22 campaign looked to be a clean slate for both DeBrusk and the Bruins after a lost season in 2020-21  — it didn’t take very long for DeBrusk to land back in Bruce Cassidy’s doghouse.

Despite offering a bit more of a scoring punch than the rest of his bottom-six counterparts (three goals, three assists in 17 games), DeBrusk found himself stuck up on the ninth floor on Sunday — with Cassidy noting that the second effort that they were looking for was starting to tail off as his production waned. 

“I think what happens with Jake and what we’ve seen over the last few years is, like when the production is there you’re getting more second effort, they kind of go hand in hand,” Cassidy said. “When it’s not there, we lose a little bit of that. That’s been the ask of him for a number of years now — no drop off on this side of the ledger just because the production isn’t there.

“Any 20-goal scorer still only scores once every four games if they’re playing every game, more or less, so you still need the other things. A little bit more of an ask there on second effort away from the puck, working to keep it out of your net, etc. We understand certain guys can be physical when they’re not scoring or bringing something, and for him, it’s foot speed, and I’d like to see that every night. I’d like to see him impact the game with his foot speed every night in some way shape or form, whether it’s the forecheck, attacking the net, the penalty kill, whatever the case may be.

“So, that’s where we’re at, and we’re starting to see that drop off again, so it’s a reminder, ‘Hey, bring us the effort and hopefully the production happens, but we need that.’”

But at this point — with DeBrusk now back on the outside looking in at regular reps and approaching a contract year (although he will stay be an RFA this summer) — it sure seems like the hot-and-cold winger is looking to start anew somewhere else.

Given that DeBrusk’s trade request is now fully out in the open, it does create an awfully awkward situation — especially considering that Boston could likely use DeBrusk’s services in a top-six role over the next week due to Brad Marchand’s suspension.

DeBrusk might be looking ahead to greener pastures, but the Bruins are now stuck between a rock and a hard place as far as securing a proper return for a player that has top-six potential — but has seen his stock plummet over the last few seasons.

Had Boston entertained offers for DeBrusk a few seasons ago — back when he was looking like a perennial threat to pot 25+ goals a season — then maybe Boston could bring in a useful asset to solve their current woes, whether it be a legit top-four blueliner or an impactful pivot. 

But despite the number of tweets hitting my inbox that are inquiring about the possibility of DeBrusk being used to bring in a difference maker like a Tomas Hertl or a J.T. Miller — the only way Boston swings a move like that is if DeBrusk is part of a much larger package at this point.  

While I’m sure that there a number of teams that are intrigued by DeBrusk and would love to pry him out of Boston in hope of a resurgent response — Boston has next to no leverage in terms of demanding a top-tier asset, not with this trade request now public and DeBrusk’s $3.675 million cap hit not the easiest pill to swallow in this cap-crunched league.

Boston would likely want to see what the return could be if they were to package more players or prospects in a deal with DeBrusk, but if the wheels are in motion and all parties are looking to pull the trigger on a deal soon — the return might underwhelm many.

Perhaps a swap for a fellow underachieving forward or winger like New York’s Ryan Strome or Edmonton’s Kailer Yamamoto? Hertl may be out of Boston’s asking price, but maybe a fellow San Jose forward in Kevin Labanc?

Or maybe the Bruins simply look to move DeBrusk’s contract off the books, and are focusing  on draft capital in return — although you might be looking more at a second-round pick at this point, if you’re lucky. 

At this point, it sure seems like a fresh start is the best move for all involved. Still, it’s disappointing to see this partnership come to an end like this — especially with Boston forced to MacGyver their way out of another situation with a sunken asset.

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