Top 20 Worst Free Agent Signings in MLB History

Free agency is a time of wonder in most sports. Teams shop around for players to add to their rosters in hopes of acquiring someone that will contribute to that team winning a championship. And we've heard of many teams in Major League Baseball in which that has been the case. Those teams that pick up that final piece of the puzzle that leads them into the playoffs and beyond.

And then there are the free agent picks ups that aren't quite what they were cracked up to be. Teams sign these prized free agents to blockbuster mega contracts, but they end up falling flatter than a pancake under a steamroller. What's even more disheartening about some of these signings is how most of these players showed no indication of slowing down. They had built these reputations of being fabulous ball players with some of them having years of success behind them to give reason for these mega million contracts that went to complete waste on these players.

Some were not only immensely talented players, but also players fighting back for redemption. Success stories that had a happy ending with the player receiving a contract that vindicated them from their past troubles and lit their futures for new and positive paths. But alas, they were not able to hold up their end of this new contract.

All of these players have gone through the ends of their respective big contracts and have moved onto success in other realms or have disappeared into obscurity altogether. The biggest thing about these debacles of signing "prized" free agents is that they're a lesson to front offices in every corner of the league to do their homework when it comes to signing someone to long-term deals. Because as bad as it is for a player to end up on this list, being the team that signed him is just as bad.

20 Manny Ramirez

Contract Worth: 2 years, $45 Million.

19 Jason Bay 


Contract Worth: 4 years, $66 Million.

18 Milton Bradley


Contract Worth: 3 years, $30 Million

17 Albert Belle 


Contract Worth: 5 yrs, $65 Million

16 Mo Vaughn 


Contract Worth: 3 years, $46.5 Million

15 Barry Zito 

Contract Worth: 7 Years, $126 Million

14 Jason Schmidt 


Contract Worth: 3 years, $47 Million

13 Oliver Perez 


Contract Worth: 3 years, $36 Million

12 Carl Pavano 


Contract Worth: 4 Years, $39.95 Million

11 Chone Figgins 


Contract Worth: 4 years, $36 Million

10 Gary Matthews Jr. 


Contract Worth: 5 years, $50 Million

9 Russ Ortiz 


Contract Worth: 4 years, $33 Million

8 Carlos Silva 


Contract Worth: 4 years, $48 Million

7 Chan Ho Park 


Contract Worth: 5 years, $65 Million

6 Carl Crawford


Contract Worth: 7 years, $142 Million

5 Melvin Upton Jr. 

Jason Getz-USA TODAY Sports

Contract Worth: 5 years, $75.25 Million

4 Andruw Jones 


Contract Worth: 2 years, $36.2 Million

3 Denny Neagle


Contract Worth: 5 years, $51 Million

2 Mike Hampton 


Contract Worth: 8 years, $121 Million

1 Josh Hamilton 

Robert Hanashiro-USA TODAY Sports

Contract Worth: 5 year, $125 Million

The saddest story on this list, Josh Hamilton's contract and story is what truly makes this the worst free agent signing. After being an inspiring story by growing into one of the best hitters in the MLB after conquering a drug addiction, Hamilton had become fuel and soul for his Rangers, winning MVP honors in 2010, leading his team into the playoffs and into the World Series for the first time, picking up the ALCS MVP in the process. A couple of years later, he signed with the Angels and his first season for the Angels was a decent one by his standards, swatting 21 homers with 79 RBI. It was in his second season where things started to unravel for the slugger. After suffering an injury that shelved him for a quite a while, his return to the lineup was less than stellar. During the ALDS against the Kansas City Royals, he went 0-13, either striking out or grounding out with runners in scoring position. Then, while recovering from shoulder surgery, Hamilton sadly relapsed into drugs. Though he was not punished by the league, the owner of the Angels didn't want any part of the embattled slugger. Hamilton is currently trying to experience a career renaissance back with the Rangers where for his sake, we hope he can get back on track.

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Top 20 Worst Free Agent Signings in MLB History