Alex Rodriguez, 2007 agreed to 10-year, $275 million, the New York Yankees
A-Rod won his second MVP as a NY Yankee in 2007 and the Yanks fell over themselves to give him truckloads of money. It seemed to be worth it when Rodriguez finally showed up in the postseason in 2009 and helped NY win a World Series. It's been brown-trousers time since then as A-Rod has found himself mired in steroid abuse allegations that could lead to a lifetime ban from MLB. At least he'll always have his millions of dollars and the matching BFF bracelets Derek Jeter bought for them.