At 5 feet 10 inches (1.8 meters) and 160 pounds (72 kilograms), Lenny Dykstra was never a physically imposing baseball player, but his on-field tenacity and clutch heroics for the New York Mets in the 1980s won him the nickname "Nails." Dykstra earned more than $36 million in his MLB career, but some of his biggest paydays came after retirement [source: Wilson].
The former baseball player invested heavily in the stock market and in real estate, even promoting himself as a self-taught financial guru. He was a frequent and outspoken guest on cable financial advice shows and published his own investment guide for athletes called the Players Club. For all of his Wall Street savvy, however, Dykstra failed to forecast the housing bust and stock market collapse of 2007.
Dykstra's fall from financial grace was even uglier than his late '80s mullet. After declaring bankruptcy in 2009, he was convicted of bankruptcy fraud for trying to sell or destroy property that should have belonged to his creditors. His sentence of six months was served on top of an existing conviction for grand theft auto [source: Schilken]. Dykstra also made court appearances for indecent exposure and drug possession [source: Chan]. Say it ain't so, Nails!