The Bruins already have enough roster questions on the table, but two of the biggest ones are tied to Pavel Zacha and Casey Mittlestadt.
Both forwards are pending free agents after the 2026-27 season, and that makes their long-term fit in Boston a live issue for Don Sweeney and the front office. Zacha looks like the kind of player the Bruins would want to keep around, but the real question is what it would cost. With the cap rising, every extension is going to come down to how far a team is willing to go.
Mittlestadt is in a similar spot, though his path feels a little murkier. He has been part of trade chatter for more than a year, and that talk hasn’t gone away. If Boston is sliding out of playoff position by March and the trade deadline becomes a selling point instead of a holding pattern, both players could end up on the move.
That possibility came up in Joe Yerdon’s Bleacher Report piece on 10 pending free agents who could be dealt this season, where both Bruins forwards landed on the list. Yerdon wrote, "A lot of how this season goes will determine what happens with a couple of the Boston Bruins top free agents-to-be and in Pavel Zacha's case, he could be in high demand if the Bruins fall out of contention.''
Among the two, Zacha would almost certainly bring the strongest market and the best return. But moving a top-six center is no small decision for a team that already has a thin situation at that spot. Boston would need a deal that clearly justified making that kind of move.
Yerdon also pointed to Mittlestadt’s offensive talent, writing, "Mittelstadt's skill is still very good. He possesses incredible hands and scoring instincts and a quick offensive mind. As he enters the final year of his contract with the Bruins, whether his future is meant to remain in Boston or to go elsewhere that his offense can better shine remains to be seen, but if the Bruins struggle this season, the chances of Mittelstadt going elsewhere in a trade would rise,'' Yerdon wrote.
If Boston is being realistic about the two, Zacha feels more likely to stay than Mittlestadt. Mittlestadt still has to prove he can consistently match the AAV Colorado gave him, and there’s a reason the Avalanche moved him on. He did have a good season in 2025-26, but whether he can turn that into the kind of breakout that changes the conversation remains to be seen.
If the Bruins’ season starts to unravel, these two names are going to sit right at the center of the deadline discussion. Unless Zacha is extended before then, that storyline is only going to get louder.
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