5 Jason Schmidt – Los Angeles Dodgers (2007, 3 yrs. $47 million)
Before coming to the Dodgers, Jason Schmidt was widely considered one of the best pitchers in the league. In his six years with their northern rivals the Giants, Schmidt was consistently among the NL’s best in ERA, but as soon as he came south, his career went the same way. In his time with the Dodgers Schmidt was constantly hurt, missing the entire 2008 season and playing just small parts in ’07 and ’09. He tallied just 10 starts for LA, posting a 6.02 ERA, and taking home roughly $15.5 million for each win he earned the Dodgers. That’s essentially the equivalent of landing a job as a library security guard that pays $100 an hour.
4 Mike Hampton – Colorado Rockies (2001, 8 yrs. $121 million)
If you’re wondering how the hell Mike Hampton got the Rockies to give him $121 million, you’re not alone. In fact, Mike Hampton is wondering the same exact thing. Granted, Hampton had posted a 22-win season and a 2.90 ERA for the Astros just two years prior, but considering he was always just an average pitcher before that, the whole 120+ mil thing may have been just a slight over-shot. Hampton wound up playing just two injury-plagued seasons in Colorado, going 21-28 and posting ERA’s of 5.41 and 6.15, before the Rockies shipped him out of town along with the majority of their franchise’s financial holdings.
3 Carl Pavano – New York Yankees (2004, 4 yrs. $39.95 million)
Carl Pavano was coming off a career year; 18 wins, and a 3.00 ERA. The New York Yankees were still thoroughly entrenched in trying to buy up all their talent, and were apparently still enamored with the way Pavano pitched against them in the 2003 World Series. What resulted was arguably the worst contract in Yankee history. In his time in New York, Pavano was either too hurt to pitch, or just too bad at pitching, either way, New York didn’t take to him. In total Pavano pitched to just a 9-8 career record for the Yanks, never posted an ERA below 4.76, and earned roughly $4.5 million dollars for every victory he tallied in pinstripes.
2 Mo Vaughn – Anaheim Angels of California at Disneyworld (1999, 6 yrs. $80 million)
Throughout the 90s, Mo Vaughn established himself as one of the league’s most feared hitters as a member of the Boston Red Sox. So when the Angels offered him a massive contract, it seemed quite well deserved. And in his first two seasons with the Angels, Big Mo earned his dough, notching 33 and 36 home runs and going over 100 RBIs in both years. The only trouble is, that’s where it all ended. Vaughn missed the entire 2001 season due to injury, and he would never round back into form (ironically, because he literally rounded out of form). Unfortunately, Mo’s weight and the amount of days he had off had a tragically direct relationship, and the Angels were forced to ship him to the Mets where he continued to struggle and would be out of the league just two years later.
1 Andruw Jones – Los Angeles Dodgers (2008, 2 yrs. $36.2 million)
What will solve the problems of a once promising player coming off his worst year in the majors? Well, according to the Los Angeles Dodgers, just throw a bunch of unwarranted money at him. Andruw Jones came onto the free agent market after a terrible season where he hit just .222, but rather than using his sub-par stats to buy low, the Dodgers offered up a two-year deal worth more than $36 million. Then, what they thought would be a franchise center fielder, turned out to give them just one year, 3 home runs, and a .158 batting average. But the real icing on this awful cake is that the Dodgers actual franchise center fielder, Matt Kemp, was sitting on their bench the entire time.