Vincent Viola
Viola owns the Florida Panthers with moderate success. He also enjoyed a relatively decent profile off the field because the team improved inclusivity off the ice. But he made mistakes away from hockey that damaged his reputation. Donald Trump picked Viola as his nominee for Army Secretary.

But he didn’t land the gig because of his blatant corruption. Viola manipulated stock to buy government contracts before he took his job. Lawsuits emerged and made it impossible for Trump to install Viola in the role. It’s safe to say that this wasn’t the smartest move that the Panthers owner ever made (via Bloomberg).