It made too much sense to sign Montgomery, but they went and got Dollar General Montgomery instead. IDK.
It's not how I'd run a franchise.
Giolito was fine if you're hoping for him to be a 3rd/4th starter, but the Sox needed more.
Yes, he shouldn't have been the best pitcher acquired. There was a significant chance that he wouldn't outpitch Bello, Pivetta, Crawford aside from INNINGS.
I was thinking that Bloom didn't make any similar moves, but there was the Whitlock extension. Not sure why he didn't try to extend Raffy earlier. There weren't really many other notable guys around that were in need of extending during his tenure.
No real rush to add someone to the 40 man. That pitcher may get a minor injury prior to the start of the season. Just do the roster moves at the end of camp unless you need to add an unsigned guy.