Torii Hunter

Raghib Ismail

Art Monk

Michel Vick

Mike Pelfry

Antoine Winfield

Antoine Winfield — the top-ranked defensive back in the country in his draft class — was a first-round pick out of Ohio State University. Unfortunately, the standout defender soon saw half of his $3.5 million signing bonus go down the tubes when his close friend and adviser Dunyasha Mon Yetts pilfered the funds in the name of responsibly managing Winfield’s investments. In reality, Yetts used the money to make highly speculative (and extremely poor) investments, and then he went even further by actually moving some cash out of Winfield’s accounts and into his own. All this was hidden from Winfield, who believed his friend was busy investing the funds for a healthy profit.
Eric Dickerson

Eric Dickerson was the fastest running back to reach 10,000 yards. He was also the fastest to believe his financial adviser was an Italian Count. Dickerson met financier Luigi DiFonzo at a Hall of Fame dinner in Canton, Ohio. He decided to invest money with DFJ Italia after Difonzo convinced the table he was of Italian nobility. What Dickerson didn’t know was that DiFonzo was a two-time felon. This steely scam artist targeted NFL players and Dickerson soon became one of his victims. Mamma mia!
Fred Taylor

First-round draft pick Fred Taylor invested his money with super agent William “Tank” Black. The Tank represented many star athletes, including Sterling Sharpe and Vince Carter, and was eventually able to accumulate over 50 professional athlete clients. Black would wind up going to jail over allegations of a ponzi scheme, money laundering, and a Securities and Exchange Commission stock-swindling case. Taylor claims that Black’s scheming cost him nearly his entire $5 million rookie signing bonus.
Terrell Davis

John Elway

This Super Bowl MVP and former teammate of Terrell Davis has thrown up some Hail Marys in his day, but none greater than this particular hedge fund investment: Elway and a co-investor committed $15 million to what turned out to be a ponzi scheme run by hedge fund manager Sean Mueller says The Denver Post. Elway and his business partner weren’t the only victims: Mueller collected some $71 million in funds from over 60 investors. Don’t hurt too bad for Elway — he’s had plenty of business success.
Johnny Unitas

This all-time great quarterback came from humble beginnings and worked hard, but the peaks and valleys of entrepreneurship got the best of Johnny Unitas. Johnny retired from football in 1973 and by 1991 was bankrupt. His failed business ventures included bowling alleys, restaurants and real estate.
Darren McCarty

This Detroit Red Wings forward won four Stanley Cups and was known as one of the most physical men on the ice. It may be time to put those fists to work off the ice as well: McCarty’s business partner took a $3 million loan out of the big man’s personal savings account and, in a completely separate instance, forged McCarty’s name on a $650,000 check! Where’s an enforcer when you need one?
Sheryl Swoopes
Sheryl Swoopes was often compared to Michael Jordan on the basketball court, but off the court she’s become another cautionary example of someone who can’t “Be Like Mike” when it comes to making money. Swoopes earned over $50 million throughout her illustrious WNBA career — wait, $50 million, can we get a fact-check on that? — but wound up filing for bankruptcy in 2004. A victim of poor representation and even worse investments, she would wind up owing her creditors some $750,000.
Travis Henry
Sharing the backfield at the University of Tennessee with ex-con Jamal Lewis, Henry indulged in some of the same mistaken habits as Lewis — mainly cocaine. Lewis would only get 4 months in prison after dealing the illegal substance and would end up much luckier than Henry. The Pro Bowl running back would have to pay over $4 million in fines and is currently serving a prison term for drug trafficking according to USA Today.
Deuce McAllister
The chants of “DEUUUCE,” can still be heard when one enters the Louisiana Superdome, where this fan-favorite running back played. Unfortunately, McAllister’s Jackson, Mississippi Nissan dealership didn’t go as well as his NFL career. McAllister owes Nissan $930,000 and had the dealership’s inventory trucked away by an eighteen wheeler. The dealership filed for chapter 11 bankruptcy and faces $5 million in lawsuits.
Scottie Pippen
This ex-Chicago Bull and NBA Champion famously supported Michael Jordan on the basketball court, but couldn’t quite match his teammate’s business savvy off the court. Pippen’s famous investment in a private jet took him under. The NBA swingman is seeking restitution from a firm that he claims owes him at least $8 million after misguiding him on investments. In a separate financial blunder, Scottie lost a $3.5 million investment in a South Side real estate deal.
Mark Brunell

This speedy left-handed quarterback once led the University of Washington to their second straight Rose Bowl victory over the Michigan Wolverines. Now Brunell is bankrupt with over $25 million in debts. His company Champion LLC, which included former Jaguars teammates, squandered money in multiple real estate ventures in Grand Rapids and Traverse City. After all the losses Brunell says bankruptcy has reaffirmed what is most important to him: faith, family and friendships.