I would say yes, if you define success in the political game as being elected to a high office. Most of us consider him an idiot, and in many way he certainly is. But he do knows who to get people to vote for him, which is what matters. He didn't fall into the precidency by accident or by being rich or well connected. He did what mattered to become elected (with a bit of help from Putin).

Many smarter people with more money and better connections failed, see e.g. Bloomberg.