20 Bad Free Agent Signings MLB Teams Are Still Trying To Recover From

As luck would have it, we in North America are fortunate to have four major professional sports leagues, all of which feature the best players that the world has to offer, but of those sports, only one has been around for 115 years. Major League Baseball was founded in 1903, and unlike the NFL, NHL, and NBA, it is a league dominated by statistics and longstanding traditions. There are those who think that baseball is too long and dull, but the MLB has provided sports fans with some of the greatest moments in history, moments that could have only happened thanks to the players who actually play the game.

It may look easy, but baseball is actually extremely difficult to play, from the pitchers who need to have command of every pitch, to the position players who have to field a fast moving ball, and who also have to try and hit it. Like every sport, baseball players get paid based on what they do on the field, and those who perform better always earn more money, but not all those players live up to their contracts, either because of poor production, injury, or some combination of the two. Teams tend to do well with some of the big money contracts they hand out to free agents, but the MLB is littered with teams who have made terrible deals, some of which were done in the past, and some which are going on right now. No matter when these contracts were actually signed, the teams regretted them for years afterwards, and this article will identify 20 of these terrible free agent signings.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

20 Josh Hamilton

via latimes.com

The Angels currently have Mike Trout, Shohei Ohtani, and several other good pieces, but a few years ago, they also had former outfielder Josh Hamilton, who they signed in 2013 to an insane 5-year, $125 million contract. At the time, the contract seemed way too big.

The Angels ended up looking like fools as Hamilton posted a .255 batting average with just 32 home runs in 240 games, while also going 0-13 in the playoffs.

In 2015, he dealt with a lengthy injury, but he was also caught violating the league's drug policy, which prompted the team to trade him back to Texas, a move that cost them dearly, seeing as they still had to pay $63 million to ship him to their division rival.

19 Mike Leake 

Jeff Curry-USA TODAY Sports

For a long time, the St. Louis Cardinals have been regarded as the best run franchise in baseball, which is why it is so surprising that they signed Mike Leake to an outrageous contract. Following a decent 2015 season, the Cards signed Leake to a 5-year, $80 million contract, which was the biggest contract that the franchise had ever given to a pitcher.

In parts of 2 seasons with the team, Leake posted an ERA way above 4.00, which is why they decided to trade him to Seattle last year.

In return, St. Louis got a prospect who appears to be a complete bust, and they were also forced to retain $17 million of his contract, while also surrendering $750,000 in international cap space.

18 Jason Heyward

Jake Roth-USA TODAY Sports

In 2015, Jason Heyward played for the Cardinals, and everyone expected him to get a pretty significant contract when the season ended, which is exactly what the Chicago Cubs did when they signed him to an 8-year, $184 million contract. It is true that Heyward helped the Cubs win their first World Series title in 108 years, but as far as production goes, he is performing at a level that you would expect from a utility infielder, which would be fine if he was not being paid like a high-end corner outfielder.

Considering the market the past 2 offseasons, Heyward will likely not opt out of his deal this year, which means that he will continue to make over $22 million until 2023, a salary that the team is already regretting considering the talented young players they will need to pay in the coming years.

17 Jacoby Ellsbury

Kim Klement-USA TODAY Sports

Jacoby Ellsbury spent the first 6 years of his career with the Red Sox, and helped them to win their last 2 World Series, and following the 2013 championship, the Yankees decided to steal him from their rivals by signing him to a 7-year, $153 million contract. It is true that the former All-Star has shown signs of brilliance since signing with the Yankees, but for the most part, the deal has been a complete miscalculation on their part.

Now that New York has Giancarlo Stanton, Ellsbury has fallen in the depth charts to the team's 4th or 5th outfielder, which would be fine if he were not making over $21 million a year, including this year where he has not played in a single game.

16 Albert Pujols

Amy Kontras-USA TODAY Sports

While playing for the Cardinals from 2001 to 2011, Albert Pujols was instrumental in the team winning its last 2 World Series titles, and because of how well he performed, he became the most sought after free agent in 2011. It was the Los Angeles Angels who won the bidding war, and signed the first baseman to a 10-year contract worth $254 million, which will see him make at least $28 million for another 3 years.

Pujols is without a doubt a future Hall of Famer, but his offensive numbers have been declining for years now, and if his enormous contract was not bad enough, once it is done, the team will then have to pay him $2 million for 10 years as part of a personal-services contract.

15 Wei-Yin Chen

Steve Mitchell-USA TODAY Sports

While playing for Baltimore in 2015, Wei-Yin Chen had the best season of his career, and posted a 3.34 ERA in 191.1 innings, which is why he received a nice payday when the season was over.

The Marlins signed Chen to a 5-year, $80 million dollar contract, which would be fine if he had not played in just 9 games last season, while sporting an ERA above 5.60 this season.

As some of you may know, the Marlins recently changed owners, who have made shedding salary their top priority, but because of Chen's performance, and the fact that he is still owed over $50 million, it will be almost impossible to make a deal with another team.

14 Ian Desmond

Isaiah J. Downing-USA TODAY Sports

Ian Desmond made a name for himself while playing for the Washington Capitals, and when he became a free agent in 2016, he used that notoriety to gain a 5-year contract from the Colorado Rockies worth $70 million. Last year was his first year with the team, and not only did he hit just 7 home runs, he also missed nearly half the season due to a metacarpal fracture.

This season, Desmond has been much healthier, and he is on pace to hit around 25 home runs, but he is also hitting under .240 with an on base percentage of just .309. Seeing as he is the highest payed player on a team with a lot of rookies who need to get paid, his contract is going to give the front office headaches for the next 3 years.

13 James Shields

via sandiegouniontribune.com

When a starting pitcher manages to pitch over 200 innings for 8 straight years, they develop a reputation for being healthy and reliable, and in James Shields' case, he was also fairly decent while with the Rays and Royals. When he became a free agent in 2015, the San Diego Padres signed him to a 4-year, $75 million contract, which was a franchise record at the time.

In parts of 2 seasons with the Padres, Shields posted a 4.00 ERA and a 4.45 FIP, which is why he was traded to the White Sox in 2016, a move that helped trigger San Diego's rebuild, a rebuild that saw them retain $22 million of his salary.

12 Pablo Sandoval

Bill Streicher-USA TODAY Sports

The Boston Red Sox are on the verge of having another winning season, which is a big deal for the team, especially when you consider how passionate and toxic the team's fans happen to be. Pablo Sandoval won 3 World Series titles while with the San Francisco Giants, and was named the MVP in 2014, so when he became a free agent later that same year, Boston signed him to a 5-year, $90 million contract.

Sandoval spent parts of 3 injury plagued seasons with the Red Sox, where he had a combined batting average of .237, and when they finally decided to release him last year, the team was stuck having to pay him just over $40 million to make him play elsewhere.

11 Carl Pavano

via riveraveblues.com

The New York Yankees are one of the most iconic and successful teams in all of professional sports, but just because they have won 27 World Series titles, does not mean that they have not made some costly mistakes. While with the Marlins, Carl Pavano helped the team win the World Series, and thanks to that performance, the Yankees signed him to a 4-year, $39.9 million contract.

Pavano's entire time with the Yanks was marred with injuries, which included bruised buttocks, and those injuries resulted in him making just 26 starts over those 4 years, where he put up a nice 5.00 ERA.

10 Shin-Soo Choo

Kevin Jairaj-USA TODAY Sports

We have seen quite a few players come from Asia to have lengthy MLB careers, and when Shin-Soo Choo decides to retire in 2020, he will have played in the Majors for a good 15 years. The reason why he will retire, is because he will be 38 when his 7-year, $130 million contract with the Texas Rangers comes to an end, and despite Texas' recent woes, he has performed well for them.

The problem though is that he is being paid superstar money, and when he has a paltry 5.1 WAR and a lowly .779 OPS, he is by no means a superstar.

If the re-building Rangers want to get any pieces for him in a trade, they are going to be forced to retain most of the $45 million he is still owed.

9 Chris Davis

Marilyn Indahl-USA TODAY Sports

The Baltimore Orioles are having a terrible season, and by the looks of it, they will not be getting better anytime soon, and a big reason for their poor performance lies with the faith they put into their first baseman, Chris Davis. Baltimore may have acquired Davis via trade in 2011, but when he became a free agent in 2016, they made sure to re-sign the home run hitter, giving him a 7-year deal worth $161 million.

In 2016, he hit just .221, and .215 in 2017, and this year his average has dropped to under .160, making him the definition of overpaid.

Because of his bloated contract that will give him over $21 million until he is 36, he is virtually untradable, which will really hurt Baltimore salary wise until 2022.

8 Yasmany Tomas

Steve Mitchell-USA TODAY Sports

As we all know, the U.S. and Cuba have had a rather tense relationship for several decades, but that has not stopped Cuban baseball players like Yasmany Tomas from making a life for themselves by playing in the MLB. Prior to the 2015 season, the Arizona Diamondbacks signed the slugger to a 6-year, $68.5 million contract, and based on his 2016 performance, it looked like a good deal, but thanks to an injury plagued campaign last season, his career may have been completely derailed.

With another 3 years left on his deal, Tomas finds himself in Triple-A, and assuming he will exercise his player options, the D-Backs will be forced to waste another $46 million on him at a time when big free agents are set to hit the market.

7 Mike Hampton

via denverpost.com

Following the 2000 season, the Colorado Rockies decided that they needed to overhaul their entire pitching staff, which is why they went out and signed free agent Mike Hampton. They signed him to an 8-year, $121 million contract, which made him the highest paid player at the time, and as you might have guessed, he turned out to be a complete dud with the team.

After just 62 starts, the starter posted an atrocious 5.72 ERA, and luckily for the Rockies, they were able to trade him in 2002, in what was a complicated 3-team transaction that saw the Rockies get virtually nothing in return.

6 Melvin Upton Jr.

via talkingchop.com

The Atlanta Braves finished the past 4 seasons with losing records, so their performance this season has been a very welcomed sight for the team's fans, but they only had themselves to blame for those terrible seasons. In 2013, Melvin Upton Jr. became a free agent, and it was Atlanta who signed him by giving him $75.25 million over 5 years, but his stint with the Braves was a disaster.

In his first year, Upton hit an embarrassing .184, and .208 the following year, which is why the Braves decided to trade him to San Diego in 2015.

The move saw them get 4 pieces in return, of which only a mediocre starting pitcher is currently playing on the team.

5 Chan Ho Park

via pinterest.com

When Chan Ho Park first came into the Majors, he was a member of the L.A. Dodgers, and in 2001, he put up a 3.50 ERA while pitching in 234.1 innings over the course of 35 starts, a performance that made the Texas Rangers sign him that same offseason. The contract was a 5-year deal worth $65 million, and it was a reasonable contract considering that the Rangers expected him to become their new ace.

In 68 starts, Park pitched in just 380 innings, where he recorded an atrocious 5.79 ERA, and luckily for Texas, they were able to trade him in the final year of his deal, but not before he made a fool of the general manager and scouting staff.

4 Carl Crawford

via sbnation.com

Earlier we talked about the disaster that was Pablo Sandoval's contract, but over the past decade, the Red Sox have signed several other free agents to terrible contracts, including former outfielder, Carl Crawford. He made a name for himself while in Tampa Bay, and based on his reputation, Boston signed him to a 7-year, $142 million contract.

After 2 years, he was shipped off to the Dodgers after bad performances and going on the DL more than once.

Not only did Boston get stuck paying a huge chunk of his remaining salary, they also had to deal with Crawford bad-mouthing the team and their fans, stating that his experience with Boston was completely toxic.

3 Barry Zito

via sportsonearth.com

For a time, the San Francisco Giants were the best baseball team in the entire world, as evidenced by the fact that they won 3 championships in 5 years, and Barry Zito helped them to win their 2012 title. The former starting pitcher joined San Francisco in 2007, following a Cy Young winning performance with Oakland, a performance that got him a 7-year deal worth $119 million.

Like everyone else on this list, Zito's performance started to deteriorate as soon as he signed his big deal, as he finished his time with the Giants with a 4.62 ERA, and to make things even worse, they basically had him on the bench for 2 years with the team before finally buying him out in 2014.

2 Albert Belle

via chron.com

Major League Baseball has always had home run hitters, and Albert Belle was one of them, having 5 Silver Slugger Awards to show for it, and he even led the Majors in home runs in 1995. It was because of his home run potential that the Baltimore Orioles signed him to a 5-year, $65 million contract, which at the time made him the highest paid player in the league.

In his first 2 years with the team, Belle hit a combined 60 home runs, which was a pretty good start, but thanks to a degenerative joint disease, he was forced to retire, but seeing as the Orioles still had to pay him, they were forced to keep him on their active 40-man roster for 3 years.

1 Daisuke Matsuzaka

via newyork.cbslocal.com

With this entry we will be talking about Daisuke Matsuzaka, who was a big free agent signing that the Red Sox made in recent memory that turned out to be a complete let down. Daisuke signed his 6-year, $52 million contract with Boston in 2007, and managed to help them win the World Series that same year, but other than that, he turned out to not be worth the investment.

By the time his contract was done, Daisuke had a 4.52 ERA with the team, but he also missed quite a bit of time over the years due to injuries, which would have been a tolerable mistake had Boston not also paid a $51 million posting fee to get him out of Japan in the first place.

More in MLB