The 2015 draft was hilarious, but I can't fault a GM who has managed to keep Boston's window open like he has.
They were a game away from winning the cup. Their drafting overall has not been fantastic top to bottom, but they added two superstars (Swayman+McAvoy) without having to bottom out and draft high. There are a few key players they drafted like Carlo, Frederic, Lohrei. So they have gotten more than enough through the draft.
He has also done well enforcing an identity for the team, and finding under valued players with size, who can actually play. So while he hasn't won every trade, he's done well to find a lot of hidden gems who weren't valued as high as they are now since playing on Boston.
They have lost in the first round a lot, but they should get some goodwill from that cup final run.