#12: John Elway
Even football legends like the Denver Broncos Hall of Famer aren’t immune to the siren call of ill-fated investments. John Elway, a name synonymous with gridiron greatness, found himself ensnared in the web of a Ponzi scheme back in 2010, a move that cost him a staggering $15 million. His foray into what appeared to be a “hedge fund,” managed by Sean Mueller, left him and his business partner nursing hefty losses.

Elway’s financial missteps continued to make headlines in 2016 when he reportedly missed out on a potentially life-changing windfall. A tantalizing offer had come his way: a 10% stake in the Denver Broncos for a seemingly modest $15 million, with the option to acquire an additional 10% by forgoing his deferred salary of roughly $21 million. Regrettably, Elway opted out of this once-in-a-lifetime opportunity, a decision that, as ABC News reported, could have translated to a staggering $388 million windfall when adjusted for inflation in 2016.