One of the worst feelings in the world is buyer’s remorse, and the larger the purchase the worse the feeling. We’ve all been there. So, just imagine how it must feel to be a general manager in an MLB front office after spending hundreds of millions of dollars over multiple years on one player who ends up bringing the team almost zero or possibly even negative value. The owners might even feel worse since they’re the ones who provided all that lost money. But it’s a sad reality in professional sports – if you want to get the player, you have to overpay and offer contracts that extend well beyond the projected prime of a player. This means sometimes contracts as long as 10 years or more, guaranteeing players get paid handsomely well into their late 30’s and sometimes even into their 40’s. Today, let’s talk about the 10 worst MLB contracts ever handed out and find out exactly what went wrong with these deals. I’ll stick to deals at least 5 years long and with one exception I’m going to avoid current contracts.

First, a few dishonorable mentions:

Barry Zito – SF Giants: 8 years, $126 million

Zito was the best available free agent arm entering 2007 and the Giants signed the former Cy Young Award winner to a massive deal that almost immediately backfired. I remember attending his second start of the season against the Dodgers and he gave up 8 runs. He finished the year with a 4.53 ERA then led the league in losses in 2008 with a 5.15 ERA. He had a losing record through the first 5 years of his contract, but he avoids the main list, because of a nice 2012 season in which he pitched well in the playoffs and helped the Giants win a World Series.

Albert Pujols – LA Angels: 10 years, $240 million

This one just misses the main list because Pujols did provide some value for the Angels, made an All-Star team and crushed 222 homers in an Angels uniform, 4th all time. However, he was a shadow of the player they thought they were signing. Pujols was a 3-time MVP who consistently hit well over .300 and was simply the best hitter in the game when LA gave him a 10-year deal in 2012. He immediately declined and became a slow .250 hitter with power for most of his Angels career – a good player, but not one worth $240 million.

Alex Gordon – Kansas City Royals: 4 years, $72 million

After making three straight All-Star teams and helping the Royals win a pennant in 2014 and the World Series in 2015, Gordon was rewarded with a 4 year, $72 million contract deal to stay in Kansas City. He immediately declined and hit just .220 in 2016. He hit just .237 throughout the deal and never made another All Star team although he still played great defense and won 3 Gold Gloves. The Royals even signed him for one more year in 2020 in which he won another Gold Glove, the 8th of his career.

David Wright – New York Mets: 8 years, $113 million

I’ll put David Wright as a mention instead of on the main list because injuries were the sole reason for his massive decline, but it caused his 8 year, $113 million deal to be a complete disaster. He had made 6 All Star teams in 7 years and just finished 6th for the MVP after hitting .306 with 21 home runs when he signed the deal in 2013. His first year of the contract went well, although he had some hamstring issues and played in just 112 games. In 2014, he hit just 8 homers all year long with a .269 average. In 2015, he was diagnosed with spinal stenosis and played in just 38 games. Then, in 2016, while still struggling to stay on the field due to spinal stenosis, he suffered a herniated disc. Wright tried to rehab his injuries but setbacks occurred and he could never make a full-fledged comeback although in 2018, he was activated for the last home stand of the season and made 3 plate appearances, walking once.

Ryan Howard – Philadelphia Phillies: 5 years, $125 million

During the late 2000’s one of the best hitters in the game had to be Ryan Howard of the Phillies, who won a Rookie of the Year in 2005 and an MVP in 2006 after crushing 58 homers with a .313 average. From 2006 to 2009, he averaged around 50 home runs per season. The Phillies thought they had a future Hall of Famer and wanted to make sure they locked him up so he could be spend most if not all his career in Philadelphia. That’s about the only goal that was achieved with a 5 year $125 million extension offered to Howard in 2010. The new contract kicked in in 2012 and that’s when the decline began. During an injury-riddled season, he hit just .219 with 14 home runs. In 2013, he suffered a torn left meniscus and played in just 80 games. He finally played in a full year again in 2014 but hit just .223, leading the league with 190 strikeouts. His numbers continued to decline and in 2016, he hit .196 in his final year of the extension and MLB season. At least he finished out his contract – but the same can’t be said for every one on the main list, which starts now.

TOP 10:

10. Anthony Rendon – Los Angeles Angels: 7 years, $245 million

I was going to avoid putting current contracts, but I have to make an exception for Anthony Rendon. I’ll put him at #10 since he still has time to get it together, but I wouldn’t bet on it. For his first 7 years, Anthony Rendon established himself as one of the best overall players in Major League Baseball. The third baseman played stellar defense, won multiple silver sluggers, finished as high as 3rd for the MVP and helped the Nationals win it all in 2019 after hitting .319 with 34 homers, and a league-leading 126 RBIs and 44 doubles. He was one of the top free agents entering 2020 and the Los Angeles Angels signed him to a 7 year $245 million deal that seemed to make sense at the time, but what they didn’t know at the time was – Anthony Rendon doesn’t really like baseball, which makes it kind of tough to play through nagging injuries when players hit their thirties. Incredibly, Rendon, after 5 years of this contract, has not played in 60 games yet for the Angels. In 2020, it took 29 plate appearances for him to get his first hit, although he finished the year with decent numbers including a .286 average and 9 homers. In 2021, however, he hit just .240 with 6 home runs, missing most of the year with various injuries. In 2022, he was again hurt almost all season long and was suspended for his part in a brawl. He hit just .229 with 5 homers. The spiral continued in 2023 as he got into an altercation with a fan and was suspended 4 games. He hit .236 with 2 home runs. In 2024, he landed on the injured list again multiple times and hit a career low .218. His contract has been an absolute disaster and he admitted this year that baseball has never been a priority for him and they need to shorten the season. Well, it seems it’s already been shorted for him as Rendon has played in about 37% of the Angels games since signing that 7 year deal.

9. Jordan Zimmermann – Detroit Tigers: 5 years, $110 million

One of the premiere free agent pitchers entering into the 2016 season had to be Jordan Zimmermann, who had recently made 2 All Star Games with Washington and led the league with 19 wins in 2013. In 2015, he had a slightly high 3.66 ERA, but was still solid and had just had his 4th straight season of at least 32 starts. He had proven to be healthy and effective, so The Tigers decided to give him a 5 year deal worth $110 million. He never made 30 starts in a season for Detroit. He had a hot start in Detroit and was 5-0 after April, winning pitcher of the month. After that, things fell apart and he finished the year 9-7 with a 4.87 ERA. 2017 was even worse and Zimmermann went 8-13 with an ERA over 6 and led the league in earned runs. By 2019, Zimmermann could hardly win a game – literally. He went 1-13 with a 6.91 ERA. He pitched in just 3 games in the last year of this contract in 2020 with a 7.94 ERA. For his 5-year stint with the Tigers, his WAR was in the negatives.

8. B.J. Upton – Atlanta Braves: 5 years, $72.5 million

Upton was a former Tampa Bay Devil Rays second overall pick who could fly on the basepaths, make sparkling plays in the outfield and absolutely crush a baseball. In 2012, his last year with Tampa Bay, he smashed a career high 28 bombs, his 3rd season hitting north of 20 home runs. He was one of the hottest free agents available and the Braves signed him to the biggest deal in franchise history. His stats immediately plummeted and he looked like a completely different player. After averaging 39 steals for 5 years, he stole just 12 bases and hit a mere 9 homers with an abysmal .184 batting average. He had a negative 1.7 WAR that season and did not improve much from there. In 2014, he hit .208 with another WAR in the negatives. To get rid of him, the Braves had to package him in a deal with their elite closer Craig Kimbrel and ship him off to San Diego for prospects. He played slightly better there for two part-time seasons before being traded to the Blue Jays, where he hit .196 and was released before the final season of his contract. He signed minor league deals with the Giants and Indians later, but never made it back to the big leagues.

7. Madison Bumgarner – Arizona Diamondbacks: 5 years, $85 million

By the time MadBum reached free agency in 2019, he was a 4-time All Star and postseason legend who had finished in the top 5 for the Cy Young Award 4 times. He was basically unhittable in the postseason and had a .25 ERA in 5 World Series starts. However, he was entering into his thirties and had recently experienced a couple injuries, one from a dirt bike accident. His velocity was down a bit and in 2019, he had just gone 9-9 with a 3.9 ERA, but still struck out 8.8 batters per 9. The Giants offered him 4 years and $70 million but the D-Backs topped their offer. Things didn’t go well to start the deal in the Covid-shortened 2020 as MadBum struggled then suffered a back strain. In 9 starts, he went 1-4 with a 6.48 ERA. He was terrible again in 2021 apart from one 5-game stretch in which he was pitched very well and even threw a 7-inning no-hitter. But for the season, he went 7-12 with a 4.67 ERA. In ‘22, he lost 15 games and had the worst strikeout ratio in his career. He was released after 4 starts in 2023 in which he went 0-3 with a 10.26 ERA. The D-Backs had to continue to pay Bumgarner through the 2024 season. He provided a negative WAR for his services during the contract.

6. Prince Fielder – Detroit Tigers: 9 years, $214 million

After seven years in Milwaukee, Prince Fielder was clearly was one of the league’s most dominant and healthy hitters. He never missed a game and absolutely crushed the baseball. In 2011, he hit .299 with 38 bombs, finishing third for the MVP. The Tigers gave Fielder a massive 9 year deal worth $214 million. He wore a Tigers uniform for just 2 seasons. He did play well during the regular season, hitting .313 with 30 bombs, but then struggled in the postseason and hit .071 in the World Series, which the Tigers lost to San Francisco. In 2013, he hit .182 in the ALCS then pissed off every Tigers fan by saying

"It's not really tough, man. It's over. I got kids I got to take care of, I got things I got to take care of. It's over."

It’s a sentiment he had expressed before, even after the 2012 World Series loss.

Although yes, it’s a good thing to go home and take care of your kids, fans weren’t trying to hear about how little Fielder cared about losing, especially after a poor postseason performance with the bat. After some outrage in Detroit, Fielder was traded to the Rangers but he played in just 42 games in 2014 before season-ending neck surgery. He recovered enough to hit .305 with 23 bombs in 2015, but after hitting just .212 in 2016, he had to step away from baseball after a second neck surgery, as doctors would not clear him to play again. But, he did not officially retire so that the Rangers would still have to pay him through the 2020 season. Ultimately, it was the Rangers, not the Tigers, who really paid the price for this bad contract.

5. Alex Rodriguez – NY Yankees: 10 years, $275 million

Alex Rodriguez singed not just one, but two 10-year contracts during his career. The first one he signed with the Rangers in 2001, and while he played well for Texas, the team itself wasn’t that great and they traded him after just 3 seasons. He went on to win 3 MVPs for the Yankees, so the first 10-year deal wasn’t so bad. The second, however, was in many ways a complete disaster, although it has to be said that he did help the Yankees win a World Series in 2009, which is why this isn’t ranked higher. As for the bad, the controversies during this 10-year deal began before he even signed the contract when A-Rod opted out of the original 10-year deal in 2007 before even speaking with the front office, becoming an unrestricted free agent. He and his agent Boras announced this during the 8th inning of what would be the deciding World Series game between the Red Sox and Rockies, which created controversy as they seemed to want to take the attention away from the field and focus it on them. The Yankees and A-Rod eventually settled on a 10-year deal that would last through A-Rod’s age 42 season. Just a year into the contract, Rodriguez was first exposed for using PEDs during the 2003 season with Texas. He admitted to using PEDs from 2001 to 2003 but said he quit after the 2003 season. Then, in 2013, he was linked to the BioGenesis scandal and busted for PEDs again. After denying it and appealing it, he was suspended for the entire 2014 season and eventually admitted guilt. When he wasn’t suspended during the new contract, Rodriguez struggled with injuries and played in less than 100 games 3 times. He retired in 2016 before the contract was over. A-Rod did give the Yankees some value, but based on the suspensions, controversies and injuries, I’d say it ended up as a terrible deal in the end.

4. Josh Hamilton – LA Angels: 5 years, $125 million

After being picked first overall by the Tampa Bay Devil Rays in 1999, Josh Hamilton nearly threw his entire career away due to an addiction to drugs and alcohol. He missed three entire minor league seasons and was considered the biggest draft bust in MLB history when he got his life together and got a second chance with the Reds in 2007. He hit .292 with 19 home runs, displaying the incredible ability he had to hit a baseball that got him drafted first overall. After a trade to the Rangers, he became a superstar and won the MVP in 2010 with an insane season in which he hit .359 with 32 bombs and an OPS of 1.044. He made 5 straight All Star teams and crushed 43 bombs in 2012, his last year before entering free agency. Not surprisingly, teams threw money at him and Hamilton signed with the Angels, who offered a massive 5 year deal worth $125 million. There was some risk given Hamilton’s past, but he seemed to have completely changed his life. But at 32 years old, there was also the risk of a decline in performance due to age. The Angels lost both of those gambles. Hamilton declined immediately and hit just .250 with 21 homers his first year. Then, the injury bug hit and he played in just 89 games in 2014. In the ALDS, he went 0 for 13. Before the 2015 season, while rehabbing a shoulder injury, he suffered a drug and alcohol-related relapse. The Angels were done with Hamilton and traded him back to the Rangers, but still were on the hook for most of his contract. He played in just 50 more games for the Rangers in 2015, but suffered injury problems the rest of his career until finally retiring after a failed comeback attempt in 2017.

3. Pablo Sandoval – Boston Red Sox: 5 years, $95 million

After the Giants won the World Series in 2014, fan favorite Pablo Sandoval AKA “Panda” became an attractive free agent due to his elite hand eye coordination at the plate and reliable glove at third base. He had made two All-Star teams in 2011 and 2012, but also had a history of being out of shape and wasn’t exactly a top-tier superstar. The Red Sox gave him a huge contract anyway with a 5 year deal worth nearly $100 million in guaranteed money. It turned out to be an unmitigated disaster and Pablo showed up to Spring Training out of shape and had career lows in several offensive categories including batting average which was just .245. He had a negative WAR and only got worse from there. In 2016, he was overweight again and ended up missing the entire season except for 6 hitless at bats due to injury. In 2017, he was hitting .212 when Boston pulled the plug. He was designated for assignment, removed from the 40-man roster, then released after passing through waivers. They still had pay him through 2019 and did so even though he had returned to San Francisco and began to play better there. The Red Sox ended up paying Pablo about $48 million to not play for them. It was one of the most regrettable and disastrous contracts in MLB history.

2. Jacoby Ellsbury – New York Yankees: 7 years, $153 million

No list of bad MLB contracts would be complete without the 7 year Jacoby Ellsbury disaster. Ellsbury was a speedy and exciting player for the Red Sox from 2007 to 2013. He led the league in steals 3 times, won a Gold Glove and could also handle the bat, especially in 2011 when he crushed 32 homers with a .321 average, finishing 2nd for the MVP. During the 2013-2014 offseason, the Yankees penned Ellsbury to a massive 7 year deal north of $150 million. He immediately turned into a slightly above average centerfielder with decent speed. In 2014, he hit .271 with 16 homers and that was his best year in New York. In 2015, he hit just .257 with 7 homers and 21 steals. After 2 more mediocre seasons, it was announced he would miss all of the 2018 season with hip injuries and a torn labrum. He never played professional baseball again. The Yankees released him in November of 2019 and still owed Ellsbury $21 million along with a $5 million buyout for 2021. They tried to not pay him, claiming he received an unauthorized medical, so the MLBPA filed a grievance. They won the case and the Yankees were forced to pay Ellsbury the owed money on his disastrous contract.

1. Chris Davis – Baltimore Orioles: 7 years, $161 million

It had to be the most epic performance meltdown ever for a player who just signed a massive contract extension and, in my opinion, it’s the worst contract in MLB history. From 2012 to 2015, Chris Davis was one of the Orioles’ most productive bats and he had just smashed a league-leading 47 home runs with a .923 OPS. He was an All-Star, Silver Slugger and finished as high as 3rd for the MVP. He was also not even 30 years old yet, so the Orioles did what seemed like the logical thing and secured his services for the foreseeable future with a 7 year extension. In 2016, he led the league with a career high 216 strikeouts and hit just .221. But this was just the beginning of the collapse. In 2017, he hit just .215 and in 2018, he became perhaps the worst single-season hitter in MLB history, hitting .168 with a slugging percentage under .300. Even Duane Kuiper, who hit one career home run, slugged .316. In 2019, Davis made history and completed 54 consecutive at bats without a hit, an MLB record for a non-pitcher. In 2020, he hit .115 and missed most of the season with a knee injury. He missed all of 2021 after hip surgery and then retired. However, much of the contract was deferred and the Orioles will still be paying Chris Davis through 2037.