10. Michael Jordan
Michael Jordan has struggled with very few things in his illustrious professional career. But one of the few things he did struggle with is selling his 56,000-square-foot mansion in Chicago. It’s sat on the market for over three years, even though he’s dropped the price to just under a “measly” $15 million. The home has basically been described as a “mini city,” with a regulation-size basketball court, a gym that could put most health clubs to shame, a putting green, a full service hair salon, a mammoth wine cellar, a game room, theater room, and stunning office. Seems like a pretty sweet investment if you have $15 million just laying around.