RealClearSports.com recently ranked the top 10 worst MLB free agent signings of all-time.

#1 Chan Ho Park Signed by Texas in 2002, five years, $65 million.
Coming off 18-10 and 15-11 seasons in the pitchers’ heaven that is Dodger Stadium, Texas gave Park one of the most lucrative contracts ever given to a pitcher at that time. Injuries limited his workload, which wasn’t a bad thing considering his ERAs with the Rangers: 5.75, 7.58, 5.74, 5.66, before he was finally unloaded to San Diego in 2005.

#2 Juan Pierre (signed by Los Angeles in 2006, five years, $44 million) and Andruw Jones (signed by Los Angeles in 2007, two years, $36.2 million).
You know it’s a really bad signing when the team inks someone a year later to play the same position, and he does even worse. Pierre took his below-league-average on-base ability and minuscule power into the offensive void of Dodger Stadium with predictable results: .664 and .655 OPS in his two seasons so far. Andruw Jones received a raise off his worst season in 2007, and demonstrated that bad year in Atlanta was no fluke, batting .158 with three home runs in 209 at bats in 2008. The Jones signing also shifted Pierre to left field, where his wretched bat for a centerfielder would be an even greater liability. By the end of the season, the Dodgers recognized their CF answer had been there all along, in the person of Matt Kemp.

#3 Mike Hampton and Denny Neagle – Signed by Colorado in 2000; Hampton for eight years, $121 million, Neagle for five years, $51 million.
The vertiginous problem of pitching in Colorado led to some terrible decisions. Even though importing a free agent had failed in the case of Darryl Kile (ERAs of 5.20 and 6.61 in his two seasons before he was traded to St. Louis), the Rockies tried again in the 2000-01 offseason, giving $172 million to two lefthanders. Hampton was hampered by injuries and ineffectiveness in his two seasons in Colorado, going 21-28 with ERAs of 5.41 and 6.15 before being shipped off to Florida (and then on to Atlanta); his free-agent contract finally expired last year. Neagle was a decent 31-year-old pitcher with a 105-69 record and 3.92 career ERA when the Rockies elevated him to the front of their rotation; he gave them three seasons of 19-23, 5.56, before earning his release with two years left on his contract.

I’m a little surprised Barry Zito didn’t make the list, but I guess people are willing to give him one more year of brutal pitching before really laying the hammer on the massive free agent bust.