The last time Jake DeBrusk signed an extension with the Bruins, it came on trade deadline day – March 21, 2022 – at a time when most thought he was more likely to be traded than extended thanks to an outstanding trade request.
As DeBrusk now approaches the last few months of the two-year contract he signed that day, he is hoping to avoid such chaos this time around. For starters, he has repeatedly made it clear that he wants to remain in Boston for years to come – something that was not clear at all two years ago.
He reiterated that notion again on Sunday, and said he is optimistic about something getting done.
"I always have optimism," DeBrusk said. "I feel like it would be pretty depressing if I didn't have optimism that I'd be here. It's one of those things that I hope it gets done. You know, I have an agent for a reason. I've obviously been in this organization for my whole career. So, I feel like I know where I stand in this lineup. I feel like I know where I am with the guys in this room, and the city as well, the highs and lows."
DeBrusk has certainly had plenty of both the highs and lows. The lowest point would have to be that day in Nov. 2021 when he decided to go public with his trade request. That came after a healthy scratch amid a slow start to the season, and on the heels of a career-worst 2020-21 season.
But then came some more highs: A strong finish to that 2021-22 season, and then career highs across the board in a 2022-23 season that also saw him play the role of Winter Classic hero.
This season started on a low (11 points in his first 31 games), but has recently had more highs (14 points in 16 games since Christmas).
All of it makes projecting DeBrusk's next contract difficult. At his highs, he looks like a player worthy of the kind of contract Brandon Hagel signed with Tampa Bay last summer (8 years, $6.5 million AAV) or Owen Tippett just signed with Philadelphia (8 years, $6.2 million AAV) – although DeBrusk is two years older than those two, so the length would likely be shorter. At his lows, he looks like he's barely worth the $4 million he's making now – although his defensive improvement has given his game a baseline that's higher than it was earlier in his career.
Don Sweeney and the Bruins front office have to account for both ends of the spectrum. DeBrusk and his agent have to decide if they're OK with compromising in order to stay put, or if they want to bet on a strong finish and try to cash in on the open market. A trade prior to the NHL's March 8 deadline remains a possibility, although it would have to be for a clear top-six upgrade in order for it to make any sense for the first-place Bruins.
DeBrusk has never tested unrestricted free agency. Based on his comments Sunday, he doesn't sound like someone who is especially interested in doing so now.
"People more so ask me about the fascination of it, but hopefully it doesn't get to that point," DeBrusk said. "That's kind of what I come from, is I don't even want to have that option. In saying that, it is first [kick] at the can, so I understand that too. But like I said earlier, hopefully it gets done."
The longest contract of DeBrusk's career to date was his three-year entry-level contract. His two extensions since have both been two-year deals. He would like something longer-term this time around, but whether the Bruins want to make that kind of commitment remains to be seen.
"I think I'm more so open probably to longer term. I think everybody wants to be a Bruin for as long as they can," DeBrusk said. "I don't have a number that I'm exact on on either side, honestly. I think that goes to kind of my agent and Don to get down to the numbers, all that stuff. But I think everybody would love to be a Boston Bruin. I've been lucky enough to be here for seven years now. I wouldn't mind getting another, however many more I can get. I've really enjoyed my time here."
