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.

Manny Ramirez. The dreadlocked slugger who was one of the most feared hitters in baseball is also the owner of one of the most notoriously bad contracts ever. After his most productive years as a Red Sox, he was traded to the Los Angeles Dodgers where he finished out his 2008 season with 37 home runs and 121 RBIs. He entered free agency after that year before signing back on with the Dodgers, but it came at a steep price. Slapped with a 50 game suspension after he was found to be taking an illegal female fertility drug, Ramirez was never quite able to recover his old form. Several stints on the disabled list limited his playing time and effectiveness as a hitter and Ramirez was out of LA and into obscurity. Strangely enough, he is one of the few players on this list who's statistics aren't significantly bad. His lack of playing time due to being hurt or suspended is what truly hurt this transaction.

19 Jason Bay 


Contract Worth: 4 years, $66 Million.

One of the best players to ever come out of Canada, Jason Bay was a consistent and powerful force, averaging 30 home runs, 99 RBIs, and a .279 batting average over his years with the Pirates and Red Sox. With him entering his physical prime, Bay signed a huge contract with the New York Mets, hoping to cement himself as one of the best ball players in the world. This is where the dreaded injury bug bit Bay hard. A concussion in his first season with the Mets and constant injuries to his ribs derailed Bay's rising star and made it near impossible for him to return to his consistent powerful self. His last remaining years in the league saw him only averaging 9 home runs, 40 RBI, and a paltry .218 average with his last "full" season, in which he suffered a minimal injury, being in 2011.

18 Milton Bradley


Contract Worth: 3 years, $30 Million

Milton Bradley is famous for a lot of things. A strong swing, quick legs, and an even faster temper. Bradley was a player who was extremely...emotional. Various incidents off the field in which his emotions took the best of him (one incident including Bradley wanting to confront a TV announcer for what he believed to be an unfair comparison that the TV announcer made on air) were a trademark for him and something that regrettably followed him around the league. After signing an expensive contract with the Chicago Cubs, Bradley lasted one season with the organization. Disputes with officials, the front office and Lou Pinella himself (another person not known for being the most cuddly wuddly person either) ended a very roller coaster season with the Cubs. Bradley finished out this tumultuous season with 12 homers, 40 RBIs, and a .257 average before he was shipped off to the Mariners during the offseason.

17 Albert Belle 


Contract Worth: 5 yrs, $65 Million

One of the best hitters to ever grace the landscape of baseball, Albert Belle was a feared hitter that pitchers could only hope to best. He averaged an incredible 32 home runs, 103 RBIs and a .295 average per season. Even in the twilight of his career with the Orioles, he was still mashing balls, hitting 23 home runs and 103 RBI two years into the deal he signed with them. Alas, as fate would have it, Belle was diagnosed with degenerative hip osteoarthritis. This ailment would force him into retirement and put an end to this chapter of Belle's life. Sadly his inclusion on this list is only because of a very debilitating injury derailing an extremely promising end to a stellar career.

16 Mo Vaughn 


Contract Worth: 3 years, $46.5 Million

Mo Vaughn is another one of those big name hitters who experienced a long life of successful hitting, received a huge paycheck and got injured for all of their troubles. Big Mo had five consecutive years of a .300+ batting average.  He also had six consecutive years of hitting 33+ home runs before sitting out an entire year with injuries, leading up to the big contract he received from the Mets. After a decent freshmen year in New York, a knee injury forced Mo into retirement after only playing one month in 2003. Another brilliant career that was cut short by injury.

15 Barry Zito 


Contract Worth: 7 Years, $126 Million

One of the Big Three from their days with the Oakland Athletics, Barry Zito was one of the most dominant pitchers to ever grace the mound. With sniper like accuracy and a HUGE curveball that fell so hard off the table, it was like Houdini himself made it disappear from the strike zone. His days with the Athletics finally earned him a magnificent payday with the San Francisco Giants, where the wheels started to fall off. During his years with the A's, he had only one year in which his ERA was at a 4.00 or higher. While playing with the Boys in the Bay, he never had a season where his ERA was lower than a 4.00. Serviceable, sure, but for the money that Zito was being paid to be the ace of the staff, he was certainly not doing his part. To keep it in perspective, Zito's yearly strikeout average with the A's was 170 Ks per year, while Zito's yearly strike out average with the Giants was 112 Ks. When you sign an "ace" and all the good statistics go down and all the bad statistics go up, it seems as though the title of "ace" needs to be taken away.

14 Jason Schmidt 


Contract Worth: 3 years, $47 Million

Jason Schmidt was an effective pitcher for most of his career. With the ability to throw three pitches extremely well, with an occasional fourth thrown in the mix, Schmidt was able to accumulate grandiose strikeout totals during his time with the Giants, averaging 200 Ks a year with a sparkling 3.35 ERA in his five full seasons there. Like so many others on this list, his career was cut short by injuries. During his final three seasons, he only managed ten major league appearances after having various problems with his shoulder. It would be a condition that never allowed him to continue his career again.


13 Oliver Perez 


Contract Worth: 3 years, $36 Million

Oliver Perez is one of the curious cases on this list. He was always just an average pitcher with good enough stuff to be in the majors, but not really a game changer. So when the Mets offered him this contract in 2009, it was a head scratcher to most. Well, most people were right, as evidenced by the fact that Perez had an ERA of 6.81, three wins and a very faulty knee two years into the deal. It was easy for the Mets to release Perez of his contract as he refused to take minor league assignments to either rehab himself or fix whatever mechanical pitching problem he was having. The Mets were more than happy to be rid of Perez, being just fine with paying the last $12 million as long as he wasn't weighing down the organization at any level.

12 Carl Pavano 


Contract Worth: 4 Years, $39.95 Million

The Yankees signing of Carl Pavano was one that was met with both uncertainty and hope. Pavano had just come off of his best year as a major leaguer, posting a 18-8 record with a 3.00 ERA during the 2004 season, but historically, he was not really that good. Before his magical season, there was only one time in his six year career in which he had posted a sub 4.00 ERA. Hiwever, due to the Yankees having one of the highest payrolls in baseball and seeing Pavano as one of the hottest free agents out there, the Yankees decided that the one good year was enough for them. Like most on this list, Pavano just could not stay healthy nor return to the form that earned him that contract. Between his ERA inflating and a slew of injuries, including one injury that involved him bruising his ass and starting the season on the DL, Pavano's was definitely a bust for the Yanks.

11 Chone Figgins 


Contract Worth: 4 years, $36 Million

There seems to be a common theme with most of these players: they have good, productive years where they finally earn the big money contract that they sought, only to either be injured and/or become shells of their former selves. With Chone Figgins, it was the latter. Figgins used to be the lead off man for the Angels, averaging .292 with 40 stolen bases a year. For the Mariners, however, he just could not get the job done. His first year was a bit of a down year, hitting below his usual average at .259 that year, but stolen bases was at 42 (right around his average). After that year, his average dropped below the Mendoza line, all the way to .181 in 2012 and .188 in 2011. He was eventually replaced in the lineup due to ineffectiveness, before receiving the dreaded "designated for assignment" and has been an afterthought in major league circles ever since.

10 Gary Matthews Jr. 


Contract Worth: 5 years, $50 Million

Gary Mathews Jr. has one of the most dubious contract cases in all of major league history. Like Carl Pavano, Mathews had a magnificent year in 2006, where he batted .313 with 19 home runs and 79 RBIs for the Texas Rangers, which gained him a huge raise with the Angels that following year. However, that one magnificent year could be considered an outlier, since he had very pedestrian years preceding to his quality season. Most MLB experts expected this contract signing to be one of the worst in history because Matthews hadn't really accomplished much in his career to that point. Well, they were right. While with the Angels, he faced allegations of HGH usage, was deemed to have a bad attitude, and showcased a rapidly declining skill set which spelled doom for the rest of his career.

9 Russ Ortiz 


Contract Worth: 4 years, $33 Million

Russ Ortiz actually had a long and great career, unlike many of the pitchers on this list. A 20 game winner at one point, three consecutive years of an ERA under 4.00, four consecutive years of pitching over 200 innings and not a day spent on the DL his entire career. However, when he signed with the Diamondbacks, the injury bug hit him in the form of fractured ribs after his first couple of starts. After his stint on the DL, he was never able to recover his form, with his ERA for the season ballooning to 6.89. After a disastrous 2006 that started with a calf injury and more ugly pitching performances, the Diamondbacks DFA'd Ortiz. It's considered to be one of the most expensive cuts ever made by any Major League team in history.

8 Carlos Silva 


Contract Worth: 4 years, $48 Million

Carlos Silva is among those who didn't really earn their contracts, yet for some reason, the organization (in this case, the Mariners) that gave him the contract saw something in him. When Silva became a full time starter with the Twins, he was a decent to mediocre pitcher. He ate up innings (about 193 innings a year) and posted a 4.42 ERA. So, why the Mariners gave him such an expensive contract was beyond pretty much everyone. In his first full season with the M's, he posted the highest ERA of all qualified starters at 6.46 and had a record of 4-15. His M's stint would end in a whimper as he had only 8 games under his belt (due to a shoulder injury) with a monster 8.6 ERA.

7 Chan Ho Park 


Contract Worth: 5 years, $65 Million

Chan Ho Park's entry on this list is one of the sadder entries because of his skill. Except for one year during his time with the Dodgers, Park kept his ERA around the mid 3.00s and was a workhorse. During the twilight of his Dodgers career, he had become the undisputed ace of the staff and was even selected to be the in All Star game that year. So when he was offered a huge contract with the Rangers, it was expected that he'd be the new face of the franchise and carry the Rangers. Alas, like most of the entries, Park was taken down by injuries. After averaging close to 196 innings pitched during his starter years with the Dodgers, Park cracked the 100 inning threshold only twice during his time with the Rangers with his ERA inflating to a 5.85 average over his first three years. Most experts claim that Park's downfall could also be attributed to Arlington Park being a hitter's paradise.

6 Carl Crawford


Contract Worth: 7 years, $142 Million

The man known as The Perfect Storm, Carl Crawford was one of the most electrifying players to ever grace a Tampa Bay Rays uniform. A rare combination of speed, fielding range, fielding ability, and contact hitting, Crawford was one of the most dangerous players in the league in the mid 2000s. His lightning speed was one of the reasons he hit over .300 five out of the nine years he played for the Rays and why he stole 46+ bags in seven of the nine years he played there as well. A four time All Star, Gold Glove, and Silver Slugger recipient, it makes even the experts wonder why a player with such an incredible pedigree and skill set could not thrive with one of the most historic franchises ever. Crawford did have some debilitating injuries that limited his effectiveness, but for the money that he was paid, it seems like they should have waited a bit longer before shipping him off to the Dodgers.

5 Melvin Upton Jr. 

Jason Getz-USA TODAY Sports

Contract Worth: 5 years, $75.25 Million

The former B.J. Upton, brother of Justin Upton, was a interesting case. The potential power numbers were there, but were wildly inconsistent during his time with the Rays. He hit anywhere from 9 home runs in a year to 28 home runs and swung a anywhere from a .237 batting average to .300 even. So when the Braves offered him his mega contract, there was the hope that with his brother in the line up, it would provide a stabilizing force for Upton to bring about a more consistent batting line. Well, during his two years with the Braves, all of his numbers regressed greatly, averaging 10 home runs, .198 average, and a freakishly high strikeout rate. The downward swing of Melvin Upton Jr.'s potential bit the Braves' wallet hard..

4 Andruw Jones 


Contract Worth: 2 years, $36.2 Million

The former center fielder for the Braves was one of the best power hitters of his generation. A home run and RBI machine, he was a hitter to be feared with his ability to launch the ball out of the park like it committed some great wrong against him. What he was known for as well was not exactly having a good batting average, but that was easily overlooked due to his power numbers. So when the Dodgers signed him, they expected him to thrive there as well. As we have seen throughout this list, that hasn't exactly been the case. In his lone season with the Dodgers, he hit 3 home runs, 14 RBIs, and had a pitiful .158 average. It was almost as if it was a God-send for the Dodgers to put him on the DL (first time in his career) and not have him bringing down the line up.

3 Denny Neagle


Contract Worth: 5 years, $51 Million

Denny Neagle was expected to help the Colorado Rockies solidify their rotation along with Mike Hampton. Now, Neagle was an up and down pitcher, having fantastic years where he was a 20 game winner and an owner of a 2.97 ERA, but then having a year in which he had a 4.52 ERA. So the potential was there and hopefully a new contract would make sure the worse parts of his game wouldn't show its ugly face. Seeing the theme of how none of these players on this list thrived after getting their contracts, it is only expected that he tanked. For the money that he was paid and what the Rockies got back, Neagle's contract is one that receives the notoriety of being the worst. Posting an average ERA of 5.57 during his time with the Rockies and also being hampered by injuries during the end of his stint, most experts agree that the Rockies got shafted.

2 Mike Hampton 


Contract Worth: 8 years, $121 Million

The 1 in the 1-2 punch that the Rockies had signed to solidify the rotation also makes an appearance on this list. Mike Hampton is one of the most prime examples of a pitcher who had done well throughout his entire career and earned a huge pay day. Four straight years of over 200 innings pitched and keeping an ERA in the lesser parts of the 3.oo range, he was considered to be one of the very best pitchers in the game. For whatever reason, whether it be the Coors Field stadium being a hitter's park or people finally figuring out what Hampton's pitching repertoire is all about, every positive stat went down and every negative stat went up. After becoming a full time starter with the Astros, Hampton boasted a 3.359 ERA with a winning record every single year during those years. When he hit the Mile High City, his average ERA was a paltry 5.75. Hampton also holds the distinction of being one of those players who wasn't hampered by injury nor old age to give him the excuse of not doing well. This contract is one of the most dubious in history for getting so little for so much.

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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