Bryant is Alabama royalty: His father was Bear Bryant, the legendary Crimson Tide coach. The younger Bryant became a successful businessman, owning dog tracks that grossed millions and selling several businesses (including a cement company) for hundreds of millions. His reinsurance company, Alabama Reassurance, was implicated in a felony insurance fraud case, though Bryant came out personally unscathed. Bryant has donated more than $20 million to Crimson Tide football, and he's currently the president of Alabama's Board of Trustees.