I have a half baked theory that Donny doesnt actually want to win because winning means actually doing the job again, possibly being shot at again, etc.
Why deal with that level of stress when you can just preach rhetoric, claim you were robbed, it was rigged, the system was out to get you and ask for donations to fight "them".
Edit: Thats why he chose Vance, the more I learn about him the more I think "Why tho?"