Move that does not make sense #1 - Trading Ullmark. Period.
Okay, it's no secret that Boston has struggled to get things going consistently recently, but that doesn't mean that they should immediately trade one of their goaltenders because he is not living up to the fans' standards.
Right now, Swayman has emerged as the goaltender of the future and taken away the starting role from Ullmark, but that doesn't mean that the latter needs to get traded. In fact, with his no-trade list, who knows where you would even be able to trade him to (or if he'd be willing to waive any of it).
Having two goalies who are at the top of their game at least 80% of the time, there's really no need to trade one of them. The best course of action? Keep both of them for now and decide what to do after the season, when Ullmark's list shrinks.
Move that does not make sense #2 - Trading Jake DeBrusk
When discussing the Bruins inability to get anything going, goal-scoring is definitely part of that conversation. Unfortunately, for forward Jake DeBrusk, he has been the subject of recent trade talks.
DeBrusk, however, should not be a part of any trade talks. Part of this is due to his recent play (four points in his last 10 games), but another reason to not trade him is that he has repeatedly said that he wants to stay in Boston, something that would alienate him were to hit free agency in the offseason.
DeBrusk is also on the younger end of things for a forward at 27-years-old, so there is a chance that Don Sweeney and co. could get him to stay for cheaper than they originally thought.