Wesley Edens is an investor with an affinity for the underdog

Fortress Investment Group co-founder Wesley Edens likes a counterintuitive bet. He famously dove back into subprime lending in 2010, just a few years after the financial crisis. He and Fortress are now investing more than $3 billion to build a private passenger railroad in Florida at a time when self-driving cars are the vogue investment. In 2014, Mr. Edens became a co-owner of the NBA’s Milwaukee Bucks, betting on a team whose last championship was almost a half-century ago, and on Friday he bought a majority stake in the struggling English soccer club Aston Villa.