Worst contracts in MLB history

The Chicago Cubs signed Alfonso Soriano to an eight-year, $136 million contract prior to the 2007 MLB season. Although Soriano played well at times for the Cubs, he never played well enough to justify the $136 million the Cubs gave him. After six less-than-stellar seasons for the Cubs, Soriano was traded the Yankees.

After leading the Mets to the World Series in 2000, pitcher Mike Hampton signed an eight-year, $121 million contract with the Colorado Rockies. It was a contract the Rockies would soon come to regret. Hampton was mediocre at best in two season with the Rockies. The Rockies traded Hampton to Marlins in 2002, who then shipped him to the Braves. By this time, however, the former All-Star was a shell of the player he used to be.

The Boston Red Sox made a massive mistake when they signed All-Star outfielder Carl Crawford to a seven-year, $142 million mega-contract in 2010. Crawford’s skills at the plate regressed immensely in a Red Sox uniform, and by 2012 Boston was desperate to move Crawford. Fortunately, the Sox found a trade partner in the Los Angeles Dodgers. Although glimpses of the old Carl Crawford have seen the light of day at Dodger Stadium, Crawford is worth nowhere near the $142 million contract he is signed to.

It’s still a bit of a mystery why the Toronto Blue Jays signed outfielder Vernon Wells to a seven-year, $126 million contract in 2006. Wells was a solid player but never deserving of that amount of money. Wells failed to stay healthy during most of the duration of his mega-contract and was traded to the Angels in 2011. Wells has not appeared in an MLB game since 2013.

In the prime of his career, Cy Young Award winner Barry Zito signed a seven0year, $126 million contract with the San Francisco Giants in 2006. If there was ever a surefire free agent signing, Zito appeared to be it. Well, looks can be deceiving. Zito stunk it up for the Giants over the seven years of his contract, never finishing a season with a winning record and spending significant time in the minors.

Following the 1998 MLB season, pitcher Kevin Brown became baseball’s first $100 million man, as he signed a seven-year, $107 million contract with the Dodgers. Unfortunately for the Dodgers, Brown just couldn’t stay healthy. Although when Brown was on the mound he pitched well, rumors eventually began to swirl about possible PED use. Looking back, it’s very difficult to justify the massive contract the Dodgers gave to Brown.

After three All-Star appearances with the Boston Red Sox, slugger Mo Vaughn singed a six-year, $80 million contract with the Angels before the 1999 season. Unfortunately, after two successful seasons in Anaheim, injuries derailed Vaughn’s career. By 2003 his career had essentially ended.

It might not sound like a lot money now, but when the Braves signed former Cy Young winner Bruce Sutter to a six-year deal worth over $10 million, Sutter became one of baseball richest players ever. After saving just 23 games in 1985, the Hall of Fame closer’s body began to turn on him. Sutter’s right shoulder gave out, and he only pitched in 54 more games for the Braves before retiring after the 1988 season.

The Angels fully knew what they were getting themselves into when they signed outfielder Josh Hamilton to a five-year, $125 million contract in 2012. Hamilton had resurrected his career after immense struggles with alcoholism and drug addiction and after two mediocre seasons with the team relapsed. Rather than help their player receive the treatment he needed, the Angels chose to use Hamilton’s illness as a reason to get out of the contract they signed him to. Although Hamilton would be OK, it was an ugly situation. Hamilton was eventually traded back to his former team, the Texas Rangers, earlier this year.

After striking out a record 13 times in the 2009 World Series, the Phillies still decided to give first baseman Ryan Howard a five-year, $125 million contract. It was a move the organization would come to regret quickly. Howard’s strikeout rate increased exponentially, and trips to the DL became a common occurrence for the slugger. Howard batted just .229 with one year remaining on his mega-contract.

A top prospect, Melvin Upton Jr. never quite seemed able to figure out how to be a consistent ballplayer at the Major League level. Regardless, the Braves signed Upton Jr. to a five-year, $75.5 million contract in 2012. Upton Jr.’s stint with the Braves was a disaster, as he struggled to hit above .200 and was a constant strikeout victim. The Braves traded Upton Jr. to the Padres in 2015, where he's yet to find his footing.

A tremendous talent with serious maturity issues, the Baltimore Orioles signed first basemen Albert Belle to a five-year, $65 million deal in 1998. The contract made Belle the highest paid player in baseball at the time. Belle’s skills began to decline, however, and just two years later he was forced to retire due to a degenerative hip problem.

After eight seasons with the Dodgers, pitcher Chan Ho Park signed a five-year, $65 million contract in 2001 with the Texas Rangers. Park’s transition to the American League turned out to be a disaster. The South Korean native never finished with an ERA lower than 5.00 in four seasons with the Rangers. The Rangers eventually traded Park to the Padres in 2005.

When the Dodgers re-signed pitcher Darren Dreifort to a five-year, $55 million contract before the 2001 season, the team thought it had locked up a front-of-the-rotation starter. Injuries, however, would plague Dreifort for each and every year of the contract, and the second overall pick of 1993 MLB Draft would only win five more career games.

Southpaw pitcher Denny Neagle was a hot commodity in 2000. The Rockies signed the two-time All-Star pitcher to a five-year, $51.5 million contract but would soon regret their decision to sign the lefty. Neagle played three seasons for the Rockies, going 19-23 before an elbow injury essentially ended his career.

Coming off of an All-Star season in 2006, the Los Angeles Angels of Anaheim signed outfielder Gary Matthews Jr. to a five-year, $50 million contract. Life in Southern California didn’t work out for Matthews Jr., however, as in addition being a mediocre hitter at the plate for the Halos, he was implicated in a steroid scandal. After three disappointing season for the club, the Angels traded Matthews Jr. to the Mets.

Although he was a star in Japan, Kei Igawa’s MLB career was an immense failure. After the Yankees signed him to a five-year, $46 million deal in 2006 (in addition to a $26 million posting fee), the lefty won a measly two games in two seasons in New York. Igawa would be back in Japan by the end of 2008.

Upon signing a five-year, $29 million contract with the Mets in 1992, outfielder Bobby Bonilla became the highest paid player in baseball. Although Bonilla would make All-Star appearances in 1993 and 1995, his off-the-field antics were a drain on the Mets organization. The Mets had enough of Bonilla by July, 1995, when they traded him the Orioles, yet the Mets are still paying Bonilla deferred payments on this albatross contract.

After becoming a fan favorite in Pittsburgh with the Pirates, Jason Bay signed a four-year, $66 million deal with the Mets in 2009. Although his career in New York got off to a fast start, injuries began to take their toll on Bay. The Canadian-born outfielder failed to hit better than .259 during his tenure with the Mets. Bay and the Mets eventually came to a mutual agreement to terminate his contract one year early in 2012.

It never really made sense why the Seattle Mariners signed pitcher Carlos Silva to a four-year, $48 million contract in 2007. Silva, who was at best a mediocre pitcher before Seattle shelled out nearly $50 million to sign him, turned into a terrible pitcher when he stepped onto the mound for the Mariners. Silva went 4-15 with a 6.46 ERA in his first season in Seattle. He would be out of the Majors entirely by the end of 2010.

After going 18-8 with a 3.00 ERA for the Marlins the previous year, the Yankees signed pitcher Carl Pavano to a four-year, $38 million contract in 2004. Unfortunately for Pavano and the Yankees, injuries derailed Pavano’s tenure with the team, as he never started more than 17 games in a season for the Bronx Bombers. Pavano would go on to revive his career with other clubs, but his time as a Yankee was a failure for both sides.

After having a breakout season for the Angels in 2008, the Mariners signed infielder Chone Figgins to a four-year, $36 million contract. Figgins then proceeded to fail to hit above .200 in two of his three season in Seattle. The Mariners released Figgins one year early from his contract in 2012. Figgins is currently a free agent.

When the Arizona Diamondbacks signed pitcher Russ Ortiz to a four-year, $33 million deal in 2004, the team thought it was getting a savvy veteran starter. Ortiz then proceeded to go 5-16 with an ERA above 6.00 in two seasons with the Diamondbacks. Realizing it was a failed deal, Arizona traded Ortiz to Baltimore midway through the 2006 season.

Looking for an upgrade behind the plate, the Chicago Cubs signed veteran catcher Todd Hundley to a four-year, $23.5 million contract in 2001. With typical Cubs bad luck, however, Hundley struggled to hit over the Mendoza Line and was traded back to the Dodgers in 2003.

After six successful seasons with the Cardinals, the Mets signed base-stealing wizard Vince Coleman to a four-year, $11.95 million contact in 1990. The Mets were hoping Coleman’s addition to the club would offset the loss of star outfielder Darryl Strawberry, but it never did. In fact, Coleman’s time with the Mets was an utter disaster. Along with declining production on the field, Coleman injured star pitcher Dwight Gooden with a golf club and even tossed a lit firecracker into a group of autograph seekers in the Dodger Stadium parking lot in July 1993. The second incident caused the Mets to suspend Coleman for the remainder of the season. Coleman was eventually traded to the Royals.

After three All-Star appearances with the Giants, pitcher Jason Schmidt signed with the rival Los Angeles Dodgers in 2006. The Dodgers gave Schmidt a three-year, $47 million contract they would quickly regret. Schmidt started six games for the Dodgers before a shoulder injury basically ended his career.

Despite having a long history of injuries, the Mets still chose to sign pitcher Oliver Perez to a three-year, $36 million contract in 2009. The southpaw was never able to put together a successful season for the team, as he had many a trip to the disabled list. The Mets unconditionally released Perez in March 2011, still responsible for the remaining $12 million on his contract.

Despite having an extremely short temper, the Cubs signed outfielder Milton Bradley to a three-year, $30 million deal in 2008. Bradley played one season with the Cubs before they grew tired of his personality in the clubhouse. Bradley was traded to the Mariners and was out of baseball entirely by the end of the 2011 season.

Manny Ramirez is one of baseball’s more controversial players of recent years, and for good reason. After he propelled the Dodgers to the postseason in 2008, the club re-signed Ramirez to a two-year, $45 million contract. But in 2009 Ramirez was suspended 50 games for steroid use, and it soon became clear to the Dodgers that it was a poor choice to re-sign the slugger. The Dodgers eventually waived Ramirez, and $45 million of the club's money was wasted.

Another poor choice by the Dodgers was to sign former Atlanta Braves star Andruw Jones to a two-year, $36.2 million contract in 2007. Jones struggled to hit above .200 for the club and was a disaster in the outfield as well. Luckily, the deal was only for two years, and Jones was gone by the start of the 2009 season.