@CardboardRobot consider that a billionaire has the resources not to really care about practical outcomes. They will be fine no matter what happens.
So sure, they might think, favor the autocrat. It might be interesting, and worst case scenario they will almost definitely personally be okay.
This is just one answer to your question I'm throwing out there. Another answer is that the billionaire might honestly believe the autocrat knows what's best and will be able to manage things effectively.