10 MLB Player Contracts That Hurt Their Teams (And 10 That Paid Off)

MLB free agency is where teams can either build up a World Series championship team or a group full of overpaid underachievers.

Teams like the Boston Red Sox and New York Yankees have spent decades throwing money at top-end free agents. Most of the time, it's worked out. Look at the 2018 World Series champion Red Sox - David Price and J.D. Martinez were among their most lucrative FA pickups.

However, the Red Sox have also struck out on some big-time free agents - including Carl Crawford, Daisuke Matsuzaka, Pablo Sandoval and others. But even the Yankees - who have a great track record when it comes to free agency - have made their fair share of mistakes in the winter.

There are plenty of great risks in signing free agents to lucrative contracts in the majors. This isn't the NBA, where there's a maximum term on contracts. It's not the NFL, where only so much of the money is guaranteed - allowing teams to cut players without paying too much money.

And it's not the NHL, where you can simply buy out players and/or tempt teams with draft selections to simply take on the remaining terms of a bad contract. If you sign a massive free agent bust, you're stuck with him. It's as simple as that.

Some MLB teams have done it right in free agency - signing those one or two stars that can make such a massive impact. But on the flip side, some players made a whole lot of money to do next-to-nothing.

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20 Hurt: A.J. Burnett

via The Associated Press

After missing the postseason in 2008, the New York Yankees went on a massive offseason shopping spree. They signed stars C.C. Sabathia, Mark Teixeira, Nick Swisher and A.J. Burnett - and it wound up producing a 2009 World Series championship ring.

Well, Burnett actually didn't do a whole lot to help out the Pinstripes. He got a five-year contract worth $82.5 million, but just couldn't deliver in one of baseball's most pressure-filled markets.

In three seasons with the Yankees, Burnett totaled 34 wins against 35 losses with a terrible 4.79 ERA. The Yankees would later trade him to the Pittsburgh Pirates, ending what was easily the worst contract signing in their history.

19 Paid Off: David Price

Ezra Shaw/Pool Photo via USA TODAY Sports

For the first two years, it looked like the Boston Red Sox would forever regret giving David Price a whopping seven-year contract worth $217 million. The former Cy Young winner didn't notch a single postseason victory in each of his first two years in Beantown. Not only that, but Price often feuded with the media - once telling Red Sox analyst Dennis Eckersley to "get the (expletive) out" as the team boarded a plane.

Well, Price turned all of that around in 2018. He won 16 games in the regular season and went 3-1 in the postseason, finishing with a solid ERA of 3.46. Price pitched in the decisive Game 5 of the ALDS and World Series, guiding Boston to its fourth World Series since 2004.

No matter how Price fare in the final four years of his deal, the 2018 is more than enough to warrant the $217 million they gave him.

18 Hurt: Gary Matthews Jr.

via Alchetron

After being named to his first All-Star game in 2006, the LA Angels signed away outfielder Gary Matthews Jr. from the AL West rival Texas Rangers. Matthews hit well for contact and became one of baseball's top defensive players, so the Angels rewarded him with a five-year deal worth $50 million.

Matthews wound up spending just three seasons with the Angels, and he never came close to justifying the money. He batted just .248 with an OPS of .708. His excellent defense was non-existent, and it didn't take the organization long to realize that they simply wasted their money on him.

17 Paid Off: J.D. Martinez

Gary A. Vasquez-USA TODAY Sports

The Boston Red Sox are annually one of baseball's highest spending teams, and it's amazing just how many big fish president of baseball operations Dave Dombrowski has landed.

Dombrowski signed slugger J.D. Martinez to a five-year deal worth $110 million, but with multiple opt-outs in the contract, this really was a low-risk move for the Red Sox. Martinez batted .330 in the regular season with 43 homers and 130 RBI.

He batted .300 in the postseason and clubbed three homers with 14 RBI, winning his first World Series contract with the Red Sox. Martinez will surely opt out after the 2019 season, and thus set himself up nicely for an even bigger pay day. What a steal this was for the BoSox.

16 Hurt: Melvin Upton Jr.

via MLB.com

After a strong showing for the Tampa Bay Rays in 2012, Melvin Upton Jr. signed a big-time five-year contract with the Atlanta Braves for $75.25 million. It looked like a great deal for Atlanta at the time. He brought quality defense, great speed and above-average contact hitting.

Upton totaled just 21 home runs and 61 RBI as a member of the Braves. His batting average over his two years with the organization? A horrible .198, and the OPS of .593 left a lot to be desired.

The Braves managed to unload his contract to the San Diego Padres, so there's a silver lining.

15 Paid Off: Adrian Beltre

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After losing to the San Francisco Giants in the 2010 World Series, the Texas Rangers sought that one more piece to get them over the hump. Perennial All-Star slugger and defensive stalwart third baseman Adrian Beltre was signed to a five-year contract worth $80 million.

He wound up being worth every penny.

The future Hall of Famer guided Texas to an appearance in the 2011 World Series, where they fell to the St. Louis Cardinals in seven games. Beltre led Texas to the 2012 AL Wild Card Game, plus AL West division titles in 2015 and '16.

As a Ranger, Beltre has batted .304 with 199 home runs, 699 RBI and an OPS of .865. He helped Texas grow into an AL powerhouse. So yeah, the money was totally worth it.

14 Hurt: Carl Crawford

via The Boston Globe

A four-time All-Star with the Tampa Bay Rays, Carl Crawford left the Sunshine State to join the AL East rival Boston Red Sox - signing a lucrative seven-year contract worth $142 million.

Crawford and the Red Sox entered the 2011 season as World Series favorites, but they fell apart in September and missed the postseason; his struggles were a key reason why. Crawford batted a mere .255 with with a mediocre .694 OPS.

Crawford later said he was depressed during his time with Boston. Luckily, he was traded to the Los Angeles at the 2012 trade deadline in a massive blockbuster. The Red Sox have to be thrilled they got out of that terrible contract after just two years.

13 Paid Off: Randy Johnson

The Arizona Diamondbacks gave flame-throwing lefty Randy Johnson a four-year contract worth $52.4 million in the 1998 offseason, after a storied 10-year tenure with the Seattle Mariners franchise.

Johnson needed little time to cement himself as one of the best free agent signings in MLB history, to say the least. He won the NL Cy Young Award in his first year with the D-Backs while leading the league in both strikeouts and ERA.

Johnson also led the Diamondbacks to their first and only World Series Championship in 2001, holding off the New York Yankees' bid for a fourth straight title. Johnson was named World Series MVP after shutting down New York's dangerous lineup.

12 Hurt: Pablo Sandoval

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After winning three World Series championship rings with the San Francisco Giants, Pablo Sandoval left to chase the money. The Boston Red Sox gave Sandoval a five-year contract worth $95 million, but this contract really turned out to bite them.

Sandoval was oft-injured and didn't get much playing time due to his terrible play. In just three seasons with the Red Sox, Sandoval only played a total of 161 games. He batted just .237 in a Boston uniform with a terrible .646 OPS. The Red Sox decided they had enough and released Sandoval early in the 2017 season.

That $95 million really went to waste.

11 Paid Off: Pete Rose

via 6abc Action News

Pete Rose spent his first 16 years with the Cincinnati Reds, leading them to the World Series in 1975 and '76. The all-time hits leader (4,256), signed with the Philadelphia Phillies in 1979, on a modest four-year deal worth just $3.2 million.

The Phillies hadn't won a World Series since 1950, and they were racking up the playoff heartbreaks. But Rose turned out to be the final part of the championship roster - leading Philadelphia to a 1980 World Series title.

Rose played with the Phillies until 1983, before leaving to join the Montreal Expos. He became a hero in the City of Brotherly Love for finally getting this team over the hump and guiding them to a World title.

10 Hurt: Jason Heyward

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After a surprise run to the NLCS in 2015, the Chicago Cubs sought the opportunity to go for it. They signed away standout pitcher John Lackey and All-Star outfielder Jason Heyward from the NL Central rival Chicago Cubs.

Heyward landed an eight-year deal worth $184 million, but though the Cubs won the World Series in 2016, he had very little to do with it. Three years into his deal, and Heyward has yet to show that he's worth it.

As a Cub, Heyward has batted .252 with a mere .688 OPS. The solid defense is there, but he hasn't found the All-Star hitting form that he displayed for both the Atlanta Braves and Cardinals.

There's no way the Cubs can trade away his contract. They're simply stuck with him, and there's nothing Theo Epstein can do about it.

9 Paid Off: Reggie Jackson

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The Oakland Athletics icon signed a modest five-year contact worth $2.96 million with the New York Yankees before the 1977 season took place. Jackson led Oakland to three straight World Series championships from 1972-74, and the Pinstripes hoped he could be the final piece of a championship puzzle.

And the final piece he was.

Jackson helped the Yankees win back-to-back World Series championships in 1977 and '78. In Game 6 of the 1977 Fall Classic, Jackson hit three home runs and helped New York clinch the Commissoner's Trophy. That put him in Yankee lore forever, and cemented Jackson as one of baseball's all-time great free agent signings.

8 Hurt: Albert Pujols

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When the LA Angels signed by far baseball's top hitter to a 10-year contract worth $210 million, it was expected that they would re-emerge as a championship contender. How could Albert Pujols - a three-time NL MVP with two World Series rings on his resume - possibly flop after a storied 11-year tenure in St. Louis?

Well, the Angels continue to search for that answer.

The Angels have only made the playoffs once in Pujols' seven years here. He's compiled a mere .260 batting average and .768 OPS. Those are far off the .328 BA and 1.037 OPS numbers he posted in St. Louis.

7 Paid Off: Ichiro Suzuki

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A seven-time All-Star in the Japanese NPB league, Ichiro Suzuki decided to bring his talents overseas. The three-time PL MVP opted to join the Seattle Mariners, signing for a modest $14 million over three years.

Ichiro wasted no time making an impact in the Emerald City. He was named the 2001 AL MVP and AL Rookie of the Year and guided the Mariners to an impressive 116 wins, which matched the record set by the 1906 Chicago Cubs.

Ichiro's Mariners reached the ALCS, but they were upset by the New York Yankees. His tenure in Seattle produced 10 All-Star selections, 10 Gold Gloves, two AL batting titles and 2,542 hits over his 13 seasons with the Mariners. And this all started with a $14 million deal.

6 Hurt: Barry Zito

via CBS Sports

As the San Francisco Giants moved on from the post-Barry Bonds era, the front office was desperate to rebuild a winner right away. They signed curveball specialist Barry Zito to a seven-year contract worth $126 million in the 2007 offseason, hoping the three-time All-Star would give this team an ace pitcher to build around.

But Zito was a complete bust in the Bay Area, and he contributed very little in their 2012 World Series championship season. The Giants would have won a title without Zito, so we're not going to justify the signing here.

In seven years with the Giants, Zito went 63-80 with a horrible 4.62 ERA and 1.439 WHIP. All that $126 million did was buy the Giants a 2.0 Wins-Above-Replacement. So yeah, not really worth it.

5 Paid Off: David Ortiz

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The Minnesota Twins opted not to re-sign David Ortiz for the 2003 season, but close friend and fellow Dominican Pedro Martinez thought the Boston Red Sox should take a chance on him. So they signed 'Big Papi' on a modest short-term deal to see if he could amount to anything.

All Ortiz did in Boston was earn 10 All-Star selections while guiding them to World Series championships in 2004, 2007 and 2013. Ortiz also won seven Silver Slugger Awards and became the heart and soul leader of a Red Sox franchise that went 86 years without a championship. In 14 seasons with Boston, Ortiz finished with 483 home runs and 1,530 RBI while batting .290.

That's pretty good for a guy who signed a cheap one-year deal who came to Boston with low expectations, right?

4 Hurt: Josh Hamilton

What was there to hate? Josh Hamilton was the 2010 AL MVP and led the Texas Rangers to consecutive AL pennants - in 2010 and 2011. So when the LA Angels signed away Hamilton from their arch rivals on a five-year, $125 million contract in the 2012 offseason, it looked like a shift in the AL West landscape was about to take place.


Hamilton only spent two seasons with the Angels, batting a mere .255 with an OPS of .741. He totaled 31 home runs and 123 RBI over those two years. Luckily for the Angels, the Rangers re-acquired Hamilton in a 2015 trade, and he'd help his old team win another AL West division title.

3 Paid Off: Greg Maddux

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Greg Maddux shined with the Chicago Cubs during his seven years there, but they made a massive mistake by letting him go in free agency. After the 1992 season, the Atlanta Braves gave Maddux a five-year contract worth $28 million.

Maddux wound up forming the 'Big Three' with other Cy Young winners and Hall of Famers John Smoltz and Tom Glavine. This trio led the Braves to the 1995 World Series championship, and they won the NL East division title every year during Maddux's tenure with the franchise.

Atlanta reached three World Series in total with Maddux. He won three NL Cy Young Awards and totaled 194 wins along with 1,828 strikeouts over his 11 years with the Braves. According to my calculations, that's not bad.

2 Hurt: Mike Hampton

via The Associated Press

The Colorado Rockies gave pitcher Mike Hampton a mammoth eight-year contract worth $121 million in Dec. 2000, which was the most lucrative in MLB history at the time. It's also the worst free agent signing in MLB history.

Hampton had one All-Star appearance on his resume, and he led the New York Mets to the 2000 NL pennant. But other than that, there was little reason for the Rockies to invest this money into one guy.

Hampton spent just two seasons with the Rockies, compiling a terrible 21-28 record and a brutal ERA of 5.75. Colorado would later trade Hampton to the Florida Marlins, then they flipped him to Atlanta.

1 Paid Off: Barry Bonds

Darren Yamashita-USA TODAY Sports

The San Francisco Giants gave Pittsburgh Pirates All-Star Barry Bonds a six-year contract worth $43.75 million before the 1993 million season began. For as much as Bonds shined in Pittsburgh, few could have predicted just how much this signing would change the baseball landscape.

Bonds wound up winning a whopping five NL MVP Awards with the Giants, guiding them to three NL West division titles and a Wild Card spot in 2002. That year, the Giants went all the way to the World Series - losing to the Anaheim Angels in seven games.

Bonds also became the all-time home run king in San Francisco, retiring with 762 for his career. The Giants landed the game's best slugger for $43.75 million. Though that was a record contract at the time, it sure seems like a massive underpay 25 years later.

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