It's likely the Sox would lose a lot more games if/when they trade Quintana, Robertson, Gonzalez, etc. and if they do, I'd be OK with those losses so long as they got good returns for those players that will help them win in the future.
But even so, I would still root for them to win every game rather than root for them to lose just so they could get a higher slot in the draft which doesn't guarantee them winding up with the best players anyway.
Just win.