4. Barry Zito
In 2007, the San Francisco Giants made lefty pitcher Barry Zito one of the highest paid players in baseball. The Giants signed Zito to a seven year deal worth a whopping $126 million. To celebrate his big payday, Zito splurged on a new home in the suburbs, just outside of San Francisco. With a purchase price of $8.8 million, Zito’s pricey pad came with 2.25 acres with sweeping views of Mt. Tam and Phoenix lake, a wine cellar, a guest house; outdoor living space, and an infinity pool. When the Giants decided not to resign Zito after the 2013, he listed the mega mansion for $11.5 million. Unfortunately, just like his pitching services, there wasn’t much demand for Zito’s house. Finally, after three years, and several price reductions, Zito sold the home for $8.15 million — a loss of more than $600K from his original purchase price. We think he’ll be ok…