I hear what you're saying, but this is one thing I'm not concerned about. Howard is a happy-go-lucky follower. In ORL he had to be the leader because reasons. In LAL his leader was Kobe, and in HOU his leader was Harden. If Howard comes here his leader will be Lillard and he can finally be the happy-go-lucky follower that he naturally is. Lillard will bring him into the fold and make him feel appreciated, rather than throwing him under the bus.
This is actually the one reason I WANT us to get Howard. I'm not stoked on him, but I really want to see what happens when a known "malcontent" is teamed-up with Lillard. I think that not only would we be a better team, but it'd be a good story - and we'd be thumbing our noses at LAL/HOU.
I actually think that - if Whiteside's issues persist - he'd be harder for Lillard to lead.