Kevin Brown (2004–2005)
Back in 1998, Brown signed the first $100 million–plus contract in baseball, agreeing to a seven-year, $105 million deal with the Dodgers. While Brown had posted many lights-out seasons with his sinking fastball, he was already 33, which meant the contract would endure past his 40th birthday. The Dodgers' investment appeared overgenerous, but the Yankees came out looking far worse when they traded for Brown and the final two years on his contract in December of 2003. The Dodgers had managed to squeeze two or three decent seasons out of Brown before the Yankees went on the hook for $31.4 million with the fading starter. And the team got exactly what they deserved for such foolishness. Brown went 14-13 with an ERA of 4.95 over his two seasons in the Bronx.