No. of Recommendations: 2
During his first campaign, someone published an analysis of the convict's "financial acumen". As you say, he bankrupted 3 casinos (when the odds favor the house!), declared bankruptcy at least four times overall, and ended up with less value than if he had invested his inheritance in the S&P500 when he received it, and played golf all day instead of trying to play at "business man".
And his first run in 2016 resulted in many establishments canceling their association with him (he let hotels and such put his name on their buildings for a fee, but a lot of that revenue stream was lost when people found out who he really is).