You don't need a single Republican vote to be mayor of Chicago. And if you're an incumbent, you don't even really need to court corporate donors that thoroughly, since your competition is usually gonna run at you from the left.

So this probably isn't just 4th dimensional chess. Or maybe it is, and he just sucks at it. If the play is for a better elected position in the future, then it's a pretty bad one. The "mayor of the murder capital of the universe" label isn't going to go away even if its not really true. And spending a ton of money on the Jon Burge Institute for Torturing Black People isn't really going to shore up the Democrat base in Illinois. So he's just made himself into a uniquely un-viable 'tweener.