Gold Medal: Mike Hampton – $121 million
If any pitcher looked like he could fit in with the Colorado Rockies it was Mike Hampton, who had not only pitched well with the Astros and Mets but had developed into an excellent hitter as well. Boy was his signing a mistake. First he pitched badly, compiling a sub-.500 record in two seasons in Colorado, and then he got hurt. In the final four years of his contract, Hampton pitched in only 25 games and made $60 million, an average of $2.4 million per start.
Silver Medal: Grant Hill – $93 million
Grant Hill was one of the five best players in the NBA when he was with the Detroit Pistons. In 2000, the Orlando Magic gave him and Tracy McGrady huge contracts, and when T-Mac turned into a superstar, it looked the Magic were one of the elite teams in the Eastern Conference. But Hill just couldn’t stay healthy and he managed to finish the season just one time in the seven years he was on the team. Had Hill been healthy, Orlando had a fantastic chance to get to the finals; after all, teams like the New Jersey Nets -- with Kerry Kittles, Keith Van Horn and Todd MacCulloch in the starting lineup -- managed to get out of the conference.
Bronze Medal: Jason Giambi – $120 million
Coming off an MVP season in Oakland, the New York Yankees inked Jason Giambi to one of the most lucrative deals in MLB history. Whether it was an illness brought on by a tapeworm living in his stomach or the side effects of performance-enhancing drugs, which he was found to have used, Giambi absolutely fell apart. He managed to have a few mediocre years, but never even came close to matching the stats he put up in Oakland.