The 27 Worst Free Agent Signings in MLB History

Yoenis Cespedes fields a ball

Yoenis Cespedes just got a big contract from the New York Mets | Sean M. Haffey/Getty Images

With the new CBA in place, Major League Baseball can go ahead with free agency. The GM meetings came and went, and players are beginning to sign big contracts. Yoenis Cespedes, the best hitter on the market, quickly signed with the New York Mets for four years at $110 million. It looks like a good deal right now. But these deals don’t always work out like everyone thinks they will. Here are the 27 worst free agent deals in MLB history.

27. Andruw Jones — Los Angeles Dodgers

Andruw Jones of the Los Angeles Dodgers up at bat

Andruw Jones of the Los Angeles Dodgers | Stephen Dunn/Getty Images

In the offseason prior to 2008, Andruw Jones was coming off a season in which he hit .222 with 26 home runs and 94 RBI in 154 games for the Atlanta Braves. It wasn’t the best season of his career, or even close to the best for that fact. However, the 31-year-old was stilled viewed as highly valuable. The Los Angeles Dodgers gave him a two-year contract worth roughly $36 million. Jones was injured in 2008, getting into just 75 games and hitting .158 with three home runs. The Dodgers released him after the year, essentially paying him $36 million for nothing.

26. Kevin Millwood — Texas Rangers

Kevin Millwood pitching for the Seattle Mariners

Kevin Millwood pitching for the Seattle Mariners | Brad White/Getty Images

In 2005, Kevin Millwood had a great season for the Cleveland Indians; he led the American League with a 2.86 ERA in 192 innings pitched. That earned him a five-year $60-million contract in the offseason with the Texas Rangers, who were desperate for some decent starting pitching. Millwood couldn’t supply them with any, however. Over four years with the Rangers, the right-hander posted a 4.57 ERA in 755 innings. Texas eventually traded him to the Baltimore Orioles for the final year of his deal. He finished with a 5.10 ERA in 190 2/3 innings.

25. Todd Hundley — Chicago Cubs

Todd Hundley of the Chicago Cubs watches a ball while up at bat

Todd Hundley of the Chicago Cubs | Jonathan Daniel/Getty Images

From 1995-2000, Todd Hundley was one of the best offensive catchers in Major League Baseball. Over that time, he posted a .860 OPS with 137 home runs despite spending a large chunk of two seasons on the disabled list. He even hit 41 home runs for the New York Mets in 1996. This prompted the Chicago Cubs to give Hundley a four-year deal worth $23.5 million. But he again struggled to stay healthy. Hundley played in just 171 games over two seasons with Chicago. Even worse, he hit just .199 with 28 home runs and a .684 OPS before being traded to the Los Angeles Dodgers.

24. Oliver Perez — New York Mets

Oliver Perez of the Washington Nationals watches Wilmer Flores of the New York Mets three run home run in the fifth inning at Citi Field on July 7, 2016 in the Flushing neighborhood of the Queens borough of New York City.

Oliver Perez of the Washington Nationals | Mike Stobe/Getty Images

After coming off two consecutive quality seasons as a healthy starting pitcher, the New York Mets rewarded left-hander Oliver Perez with a three-year $36-million free agent contract. Unfortunately for New York, Perez started just 21 games in three seasons. He posted a 6.81 ERA in 112 1/3 innings and missed the 2011 season in its entirety. Even worse, he’d end up having a nice career as a reliever after signing with the Seattle Mariners in 2012.

23. Chone Figgins — Seattle Mariners

Chone Figgins of the Los Angeles Dodgers

Chone Figgins of the Los Angeles Dodgers | Jamie Sabau/Getty Images

In 2009, utility man Chone Figgins made his first All-Star team at the age of 31, hitting .298 with 42 stolen bases and an American League-best 101 walks. That earned him a four-year $36-million free agent contract with the Seattle Mariners that winter. Then his production dropped off a cliff. Over the next three seasons with the Mariners, Figgins played in just 308 games with a slash line of .227/.302/.283 with four home runs and 57 stolen bases. He sat out the 2013 season before attempting a brief comeback in 2014.

22. Alfonso Soriano — Chicago Cubs

Alfonso Soriano of the New York Yankees breaks his bat fouling the ball off in the sixth inning against the Seattle Mariners at Yankee Stadium on June 2, 2014 in the Bronx borough of New York City.

Alfonso Soriano of the New York Yankees breaks his bat | Mike Stobe/Getty Images

The Chicago Cubs were desperate to spend some money and put together a decent team in the offseason prior to 2007. So, they bid against themselves for outfielder Alfonso Soriano. The end result was an eight-year $136-million contract that had a full no-trade agreement. Soriano was excellent in his first two seasons for the Cubs, helping lead them to back-to-back division championships. But his performance dropped off after that. Soriano compiled just 1.9 WAR over the final six seasons on his contract.

21. Zack Greinke — Arizona Diamondbacks

Zack Greinke is all smiles after signing his contract

Zack Greinke is all smiles after signing his contract | Ralph Freso/Getty Images

It’s probably too soon to judge, but the sheer numbers on the contract Zack Greinke signed with the Arizona Diamondbacks qualify it for this list. Coming off a season in which he led the National League with a 1.66 ERA, the 32-year-old pitcher signed a six-year $206.5-million contract with the D-backs. He battled injuries and only made 26 starts in his first year with Arizona, with a 4.37 ERA in 158 2/3 innings. He could return to form. However, at 33, with five years left on the deal, it’s hard to see this ending as a win.

20. Daisuke Matsuzaka — Boston Red Sox

Daisuke Matsuzaka of the Boston Red Sox winding up to pitch

Daisuke Matsuzaka of the Boston Red Sox | Elsa/Getty Images

Originally signed by the Boston Red Sox after a successful career in Japan, Daisuke Matsuzaka never met up to the hype that surrounded him and his “gyro-ball” pitch. He had one decent year in Boston, posting a 2.90 ERA in 2008 but also walking far too many batters — 5.0 BB/9. Overall, Matsuzaka threw just 668 1/3 innings over five seasons with the Red Sox and had a 4.52 ERA. Not exactly what they expected to get when they invested a total of $102.6 million (counting the $51 million posting fee).

19. Chan Ho Park — Texas Rangers

Chan Ho Park of the Texas Rangers

Chan Ho Park of the Texas Rangers | Jed Jacobsohn/Getty Images

In 2001, right-handed starting pitcher Chan Ho Park had a 3.50 ERA in 234 innings and 35 starts for the Los Angeles Dodgers, making his first All-Star team at the age of 28. That offseason, the Texas Rangers gave Park a five-year $65-million contract to be the ace of their staff. It didn’t quite work out that way. Park started just 32 games over the first two seasons of his Rangers career, and finished his time in Texas with 380 2/3 innings pitched and a 5.79 ERA over the course of four seasons.

18. Jason Schmidt — Los Angeles Dodgers

Jason Schmidt of the San Francisco Giants

Jason Schmidt of the San Francisco Giants | Jed Jacobsohn/Getty Images

After a long, successful, and healthy run as one of the best pitchers on their rivals, the San Francisco Giants, the Los Angeles Dodgers decided to spend some money in 2007 to bring in 34-year-old starting pitcher Jason Schmidt. They gave him a three-year deal worth $47 million. But in reality Schmidt only pitched 43 1/3 innings in a Dodgers uniform. He started six games with a 6.31 ERA in 2007; then he sat out 2008 completely, before returning in the final year of his deal to start four games with a 5.60 ERA.

17. Albert Belle — Baltimore Orioles

Albert Belle of the Baltimore Orioles

Albert Belle of the Baltimore Orioles | Jamie Squire/Getty Images

In 1998, slugger Albert Belle had a phenomenal year for the Chicago White Sox. He posted a .655 OPS with 49 home runs. The Baltimore Orioles gave him a five-year $65-million contract that winter — a monster contract for the time — and saw him have two excellent seasons. But at 33, Belle was forced to retire due to chronic hip problems. This meant that he received around $40 million despite never again wearing a Orioles uniform.

16. A.J. Burnett — New York Yankees

A.J. Burnett of the New York Yankees

A.J. Burnett of the New York Yankees | Leon Halip/Getty Images

Needing a good starting pitcher, the New York Yankees spent a lot prior to the 2009 season. They dropped a five-year $82.5-million contract on starter A.J. Burnett, who had been with the rival Toronto Blue Jays. Burnett had a fine first season, even helping the Yanks win the World Series. His final two seasons with the team were awful; he finished his Yankees career with a 4.79 ERA in 98 starts over three seasons. New York traded him to Pittsburgh, where Burnett suddenly had a resurgence with the Pirates.

15. Mo Vaughn — Anaheim Angels

Mo Vaughn of the Anaheim Angels

Mo Vaughn of the Anaheim Angels | Stephen Dunn/Getty Images

With the Boston Red Sox in 1998, designated hitter Mo Vaughn hit .337 with 40 home runs and a .993 OPS — good numbers from the 30-year-old. As a free agent, the Anaheim Angels forked over a six-year $80-million deal for the slugger. But his production sagged almost immediately. Vaughn’s OPS dropped to .865, which was still pretty good for the time. Then, he had an injury that forced him to sit out the entire 2001 season. The Angels eventually traded him to the New York Mets, where he played parts of two seasons before retiring.

14. Milton Bradley — Chicago Cubs

Milton Bradley of the Seattle Mariners smiles as he leaves the field against the Texas Rangers during spring training at Peoria Stadium on March 1, 2011 in Peoria, Arizona.

Milton Bradley of the Seattle Mariners smiles as he leaves the field | Harry How/Getty Images

After being swept in the postseason for the second consecutive year, the Chicago Cubs decided that they needed another good left-handed hitter for their 2009 team. That prompted them to give Milton Bradley, who was known as a negative clubhouse character, a three-year $30-million contract. Bradley’s numbers that season don’t explain what an awful presence he was on that team, dropping from a .999 OPS with the Rangers in 2008 to .775 with the Cubs. Chicago traded him to the Seattle Mariners in the offseason and his career only further fell apart from there. He was out of baseball at 33 years old.

13. Kei Igawa — New York Yankees

Kei Igawa of the New York Yankees

Kei Igawa of the New York Yankees | Nick Laham/Getty Images

The same year the Boston Red Sox ponied up the money for Matsuzaka, the New York Yankees signed Japanese starter Kei Igawa. Although the money he received wasn’t bad, the posting fee made it a lot to swallow for Yankees fans. It was five years for a total investment of $46 million. Igawa had injury issues and only started 13 games for the Yankees over two seasons. He compiled a 6.66 ERA in a grand total of 71 2/3 innings.

12. Russ Ortiz — Arizona Diamondbacks

Pitcher Russ Ortiz of the Los Angeles Dodgers

Russ Ortiz of the Los Angeles Dodgers | Doug Benc/Getty Images

At the time that he hit free agency after the 2004 season, 31-year-old starter Russ Ortiz had a 4.00 ERA and 103-60 record over six healthy seasons in which he averaged over 200 innings per year. That was good enough for the Arizona Diamondbacks to give him a four-year $33-million deal. He was awful in his first year, pitching 22 games with a 6.89 ERA. Ortiz had a 7.54 ERA in six starts in his second year of the deal when the D-backs simply gave up on him, releasing him and eating around $22 million.

11. Carlos Silva — Seattle Mariners

Pitcher Carlos Silva of the Chicago Cubs

Carlos Silva of the Chicago Cubs | Jonathan Daniel/Getty Images

After a decent 2007 season as a starter for the Minnesota Twins, with a 4.19 ERA in 202 innings, the Seattle Mariners gave Carlos Silva a four-year $44.7-million contract. Through the first two years of his deal, Silva started just 34 games and had a 6.81 ERA for the Mariners in 183 2/3 innings. Seattle actually traded him to the Chicago Cubs in exchange for Milton Bradley. Then, Silva had a decent final year with the Cubs (a 4.22 ERA in 21 starts in 2010) before Chicago released him and ate the final year of his contract.

10. Gary Matthews Jr. — Los Angeles Angels

Pinch hitter Gary Matthews Jr. of the New York Mets

Pinch hitter Gary Matthews Jr. of the New York Mets | Jim McIsaac/Getty Images

Coming off a year in which he hit a career-best 19 home runs with a .313 batting average, .866 OPS, and 5.2 WAR, the Los Angeles Angels went ahead and gave 32-year-old outfielder Gary Matthews Jr. a five-year $50-million contract. He failed to live up to expectations, however, hitting just 30 home runs with a .708 OPS and -0.1 WAR over three years. The Angels ate a bunch of his remaining contract just to get rid of him. They traded him to the New York Mets where he only appeared in 36 games before retiring.

9. Carl Pavano — New York Yankees

Carl Pavano of the Minnesota Twins winds up to pitch

Carl Pavano of the Minnesota Twins | Jason Miller/Getty Images

Coming into 2004, right-handed pitcher Carl Pavano had a 4.59 career ERA in five seasons and 715 innings, topping 140 innings just once in his career due to injuries. Then, he broke out with an All-Star season in ’04, making his first All-Star team and throwing 222 1/3 innings with a 3.00 ERA. That was enough for the New York Yankees to give Pavano a four-year $40-million contract, and it was a big mistake. Pavano continued to shuffle back and forth to the disabled list, finishing his Yankees career with a total of 26 starts over three years and a 5.00 ERA.

8. Carl Crawford — Boston Red Sox

Carl Crawford walks off the field

Carl Crawford only played two seasons with the Red Sox | Jason Wickerman/Getty Images

In 2011, the Boston Red Sox signed outfield Carl Crawford to a massive, seven-year $142-million contract. At the time, few questioned the logic behind the deal — Crawford was just 29 and coming off a year in which he hit .307/.356/.495 with 13 triples, 19 home runs, and 47 stolen bases. But he declined rapidly and played just 161 games in a Red Sox uniform before being dealt to the Los Angeles Dodgers. In the first six years of his contract, he has a .271/.310/.407 slash line with 3.4 accumulated WAR.

7. Jason Bay — New York Mets

Jason Bay of the New York Mets

Jason Bay of the New York Mets | Alex Trautwig/Getty Images

That Crawford signing was intended to replace the production lost when former Red Sox outfielder Jason Bay signed with his new team, getting a four-year $66-million deal with the New York Mets. Bay had hit 36 home runs, 119 RBI, and a .921 OPS at the age of 30 in 2010, and looked to be quite deserving of the deal which he was offered. Unfortunately, things worked out poorly for Bay, who battled injuries and finished out the final four years of his career hitting .229/.314/.373 with 37 home runs.

6. Barry Zito — San Francisco Giants

Pitcher Barry Zito of the San Francisco Giants gets a standing ovation as he leaves the field in the eighth inning

Pitcher Barry Zito of the San Francisco Giants | Brian Bahr/Getty Images

Left-handed starter Barry Zito spent eight years with the Oakland A’s, winning a Cy Young Award and putting together a 3.58 ERA over 1,437 1/3 innings. When he hit free agency following the 2006 season, Zito decided to stay in the general area and sign a seven-year $119-million deal with the San Francisco Giants. But, like so many before him, his performance began to drop off almost immediately after the ink had dried. Zito’s best season with the Giants came in 2012, when he had a 4.15 ERA in 32 starts and helped them win the World Series. He finished his Giants career with a 4.62 ERA over 1,139 1/3 innings.

5. Denny Neagle — Colorado Rockies

Denny Neagle of the Colorado Rockies delivers a pitch

Denny Neagle of the Colorado Rockies delivers a pitch | Justin Sullivan/Getty Images

The Colorado Rockies always seem to be in need of pitching, and this was no more true than it was heading into the offseason prior to 2001. The Rockies signed left-handed pitcher Denny Neagle, who was 32 at the time and coming off winning a World Series with the New York Yankees, to a four-year $32.5-million deal. But Neagle would only make it three years into the contract, putting together a 5.57 ERA in 370 1/3 innings in Colorado and only starting seven total games in his final season.

4. Mike Hampton — Colorado Rockies

Pitcher Mike Hampton of the Colorado Rockies

Pitcher Mike Hampton of the Colorado Rockies | Brian Bahr/Getty Images

Also a part of the flurry of spending that offseason, Mike Hampton inked a deal with the Rockies for eight years and worth $121 million. He was bad, similar to Neagle, but cost quite a bit more money and had a much longer investment. In his only two seasons with Colorado, Hampton threw 381 2/3 innings in 62 starts with a 5.75 ERA. The Rockies moved him to Atlanta, where Hampton immediately bounced back with the Braves — he had a 3.96 ERA over the next three years before getting hurt and being forced to sit out the bulk of the end of his contract.

3. Pablo Sandoval — Boston Red Sox

Pablo Sandoval of the Boston Red Sox walks to the dugout before a game against the Detroit Tigers at Fenway Park on July 24, 2015 in Boston, Massachusetts.

Pablo Sandoval of the Boston Red Sox walks to the dugout before a game | Rich Gagnon/Getty Images

After two consecutive All-Star appearances and a World Series MVP trophy, third baseman Pablo Sandoval began to show real signs of decline in 2013. His numbers got a little worse each year, until eventually he hit free agency after the 2014 season. But he had hit .366 with a .888 OPS in 78 plate appearances in the playoffs, raising his stock enough to get a five-year $95-million contract from the Boston Red Sox. Sandoval had a slash line of .245/.292/.366 in 126 games in his first season in Boston, then wasn’t even able to get on the field in his second season. At this point, it’s hard to see him having any sort of role with the Red Sox going forward.

2. Melvin Upton– Atlanta Braves

B.J. Upton of the Atlanta Braves

B.J. Upton of the Atlanta Braves | Mike Zarrilli/Getty Images

After seven seasons with the Tampa Bay Rays, Melvin Upton (formerly known as B.J.) signed a five-year $72.3-million deal with the Atlanta Braves. He was just 28 at the time, but he had already shown some signs of decline before even arriving in Atlanta. The contract has been a massive bust, and he’s been traded twice in four seasons. Upton has played in 503 games, hitting for a slash line of .218/.288/.356 with 46 home runs. He’s still owed around $16.5 million in 2017, as well.

1. Josh Hamilton — Anaheim Angels

Josh Hamilton of the Los Angeles Angels of Anaheim is congratulated by Mike Trout in the dugout

Josh Hamilton of the Los Angeles Angels of Anaheim is congratulated by Mike Trout in the dugout | Jason O. Watson/Getty Images

The story of Josh Hamilton is long and tragic, with struggles regarding drug addiction littering his past. He appeared to have made the most of his second chance, making it to the big leagues and not only becoming an All-Star caliber player, but an MVP. At the age of 31 with the Texas Rangers, Hamilton hit 43 home runs and put himself in position to get a big free agent contract from the Los Angeles Angels. He signed for five years at $114.3 million in the winter prior to 2013, but his numbers dropped off and his addiction problems returned. Eventually, after two seasons and a mediocre .741 OPS, the Angels sent Hamilton back to the Rangers — paying nearly the entire salary just to get him off their roster.

All stats courtesy of baseball-reference.com.