Maybe I’m in the minority but I would believe while your team is in contention and fixing a huge position of need with a top 5-10 player at that position in baseball would be a smart move. I understand the concern over the contract/years left but the Sox wouldn’t be the first team to make such a move and Conforto for Cease would be a risk I’m gladly willing to take.
Unfortunately the Sox don’t have the scouting/player development that the Rays do, don’t spend money like the Dodgers, and don’t have the prospect capital like the Padres, or aren’t as aggressive as let’s say the Blue Jays/Braves/Phillies so moves like these are what they’re left with. They’re gonna have to make tough decisions to round out their roster.
In regards to pitching wins, of course it does until you don’t hit (Cubs, Sox, Reds, Indians).