Every MLB team's worst free-agent contract of all time

This offseason, the New York Mets took the biggest risk in baseball history, handing outfielder Juan Soto a $765 million contract that could possibly rise to north of $800 million. The Mets beat out big spenders like the New York Yankees, Los Angeles Dodgers, and Boston Red Sox to sign the top free agent on the market, and given Soto's age and track record, it's not hard to see why Steve Cohen and David Stearns were willing to mortgage the next decade and a half on the 26-year-old outfielder.

But while Mets fans have World Series dreams dancing through their heads, and Soto seems destined to be a first-ballot Hall of Famer someday, it's worth noting that not every big contract works out the way the team and player had hoped. Whether it's a big-money team trying to get the top player on the market or a small-market team going above and beyond to convince a star to play for them, every team in the league has found itself on the wrong side of a free-agent deal.

But which one is the very worst in the history of each franchise? Some might really surprise you, while others are still on the team today.

Arizona Diamondbacks: Jordan Montgomery (two years, $47.5 million)

After a great 2023 season, Montgomery waited until the end of March to sign a deal with the D-Backs. It looked great at the time, with original reporting pegging it as a one-year deal worth $25 million with a vesting option for 2025. That option really turned out to be a $22.5 million player’s option, one that Arizona has been trying to get out from under all winter long.

Yes, this is an incredibly short deal to be on this list, but it's hard to get worse than Montgomery was in 2024. His ERA is over 6.00, and things were so bad by season's end that Arizona moved Montgomery to the bullpen. Some older fans will mention the Matt Williams deal, while the Madison Bumgarner contract quickly blew up in the team's face. Both contracts were awful, but the Montgomery deal is literally unconscionable. He’s been worse than a replacement-level player. 

Atlanta Braves: B.J. Upton (five years, $75 million)

A former top prospect and No. 2 overall pick in the MLB Draft, Upton had blossomed into a solid all-around player with the Tampa Bay Rays before hitting the free market and signing a five-year deal worth $75 million with the Braves. He was coming off a season where he was stealing fewer bases, but he had a career high 28 home runs. He was still just 27 years old, so this contract should've taken him through his prime.

Unfortunately, Upton was so bad in his first season in Atlanta that it became a running joke. He finished the season hitting .184 and had a -1.7 bWAR. He wasn’t much better in his second year, at which point the Braves decided to cut bait, shipping him off to the San Diego Padres as part of the Craig Kimbrel deal.

Baltimore Orioles: Ubaldo Jimenez (four years, $50 million)

The Baltimore Orioles might lay claim to the worst contract in the history of baseball, giving Chris Davis seven years and $161 million back in 2016 — a deal that the team will be living down through 2037. But that was the Baltimore re-signing its own player. When it comes to free agents, though, there are still plenty to choose from.

Jimenez was two full (and very bad) seasons removed from his heyday with the Rockies when the O's signed him to a four-year deal in 2014, one that all too predictably looked awful from the start. Jimenez got chewed up and spit out by the rugged AL East, his lack of command a death knell against the likes of the Yankees and Red Sox. During his four years in Baltmiore, Jimenez posted ERAs of 4.81, 4.11, 5.44 and 6.81, including a walk-off homer to end the 2016 AL Wild Card game — while All-Star closer Zack Britton stood helpless in the bullpen.

Boston Red Sox: Pablo Sandoval (five years, $90 million)

For the most part, the Red Sox have added the right players in free agency. Heck, they have some of the best free agent signings ever, especially the Manny Ramirez signing in 2000 and the David Ortiz signing in 2003. 

The good usually outweighs the bad in Boston, but there are some contracts that are still haunting this fan base. Players like Hanley Ramirez and Carl Crawford signed for big money and failed to live up to expectations. Rusney Castillo was a huge risk that failed pretty miserably. The biggest flop of all, however, came at the sign of a pen from Sandoval.

Sandoval had become one of the most popular players in MLB with the San Francisco Giants, capturing three World Seriesearning the nickname “Kung Fu Panda” for his jovial attitude and rotund physique. What made him so beloved by the Bay, however, made him public enemy No. 1 in Boston: Sandoval drove in just 47 runs in 126 games played in year one, then played just three games before missing the rest of year two due to injury. The next season, San Francisco helped the Red Sox out and reacquired their fan favorite, ending this ill-advised experiment and securing his spot as the worst contract in Red Sox history.

Chicago Cubs: Jason Heyward (eight years, $184 million)

Heyward hadn't quite lived up to the overwhelming hype that greeted him as a rookie with the Atlanta Braaves, but he'd still established himself as one of the better two-way players in the game when the Cubs signed him away from the rival Cardinals with a massive contract in the 2015 offseason. Heyward was just entering his prime at 26 years old, so the contract should have only gotten better with age.

We’re not sure what happened, but Heyward struggled to even reach mediocrity with the Cubs. His best season came in 2019, when he had 21 home runs and 62 RBI, but his once-superlative defense steadily got worse with age. All of his other seasons in Chicago were much closer to average, and that’s not what the Cubs thought they were paying for. 

Chicago White Sox: Adam Dunn (four years, $56 million)

You could see the red flags around Dunn from a mile away, one of baseball's most all or nothing hitters who was already 31 years old. But that didn’t stop the Chicago White Sox from giving him a four-year deal worth $56 million, and sure enough, paying for the decline of a guy who was hardly an electric athlete to begin with didn't work out so well.

Dunn's first season in Chicago was legendarily bad, with just 11 homers and a .159 batting average that ranked as one of the lowest of all-time over a full season.He got better in years two and three, even making an All-Star Game in 2012, but he was still striking out way too much and combined for just 1.8 bWAR over that span. He never played a postseason game, a telling story — both for the White Sox, who thought they were on the cusp of something special, and also for any team putting a player like Dunn being in the middle of their lineup.

Cincinnati Reds: Mike Moustakas (four years, $64 million)

A contract has to be really bad for a small-market team to eat $22 million for absolutely nothing. But that's exactly what the Cincinnati Reds did prior to the 2023 season, when they designated Mike Moustakas for assignment.

When Moustakas signed his four-year, $64 million contract with the Reds in 2019, it was the richest contract in franchise history. He was coming off a career year with the Milwaukee Brewers, hitting 35 home runs and representing the team at the All-Star Game. But he never came close to those highs in Cincy; in fact, he totaled just 21 home runs combined in 184 games with the team, hitting .216 over that span.

Cleveland Guardians: Wayne Garland (10 years, $2.3 million)

Garland was great in Baltimore, and was coming off a 20-win season in 1976 when he signed a massive (for the time) 10-year deal in Cleveland. But the righty wound up only lasting five years in Cleveland, and “lasted” is the appropriate word for it: After losing 19 games in '77, arm and shoulder injuries sidetracked his career, beginning with a torn rotator cuff in 1988.

After five miserable seasons, Cleveland finally decided to cut their losses, releasing Garland in 1982 and paying his salary over the next five years.

Colorado Rockies: Mike Hampton (eight years, $121 million)

Hampton was coming off an incredible run with the New York Mets, helping them make the Subway Series in 2000, and Colorado was willing to pay a premium to convince the lefty to brave the unforgiving air of Coors Field. There was just one problem (well, besides the fact that it was the biggest contract in baseball history at the time): Hampton had a 6.88 career ERA at Coors Field going into the 2001 season. 

To the surprise of no one, Hampton collapsed in Denver, lasting just two seasons before the Rockies traded him to the Atlanta Braves via the then-Florida Marlins. The Fish agreed to pay most of Hampton’s salary for three years in order to get Juan Pierre and Tim Spooneybarger out of the deal. Pierre became a star and helped the Marlins win the 2003 World Series. Well worth the price tag that comes with Hampton (and the ability to get rid of that Preston Wilson contract).

Detroit Tigers: Javy Baez (six years, $140 million)

This was a head-scratcher at the time — the rebuilding Detroit Tigers didn’t seem like a team that was ready to make this kind of commitment to a veteran — and it’s only gotten worse with age.

Baez has been an albatross to this team, treading water for a year before falling off a cliff after the 2022 season. In 2023, he had nine home runs in 136 games. His power totally disappeared, and his plate discipline kept getting worse, to the point that the team more or less nailed him to the bench during its Cinderella playoff run this past season.

The biggest question for the Tigers now is how they can get out of this contract. This should be a winter for the Tigers should be aggressive and take risks in free agency, with their young foundational players all on team-friendly deals. But the Baez deal hangs over every potential move Scott Harris might make.

Houston Astros: Jim Clancy (three years, $3.45 million)

With all due respect to Jose Abreu, a Toronto Blue Jays star finding the bag in Texas tops our list here.

Clancy signed a three-year deal that guaranteed him $1.15 million per season, a lot of money at the time, despite the fact that the righty had established himself as a very average pitcher over 12 years in Canada. Sure enough, he was even worse with his new team, pitching to a 9-22 record and a 5.57 ERA over his first two seasons in Houston. He reemerged in year three as a decent reliever, sporting a 2.78 ERA, and went on to help the Braves reach the World Series that year after a deadline deal.

Kansas City Royals: Jose Guillen (three years, $36 million)

After a dreadful stretch which saw their winning percentage hover around .350 for most of the decade, the Royals were moving up, winning 75 games in 2008. It was time to make the right moves, starting with a bat in the middle of the lineup.

Unfortunately, Guillen was not the right move. The outfielder drove in 97 runs in his first year, but that came with negative WAR thanks to a ton of strikeouts, very few walks and some awful defense. To make matters worse, the Royals got much worse, losing 97 games in 2009 and finishing 21.5 games out of the division lead. Guillen was worse in 2009, putting up a -2.0 WAR. The Royals finally moved on in year three, shipping him to the Giants, who promptly designated him for assignment (and ended his big-league career).

Los Angeles Angels: Josh Hamilton (five years, $125 million)

Hamilton had blossomed into the best story in baseball, a former top prospect who nearly had his career derailed by addiction issues only to battle back and become an AL MVP with the Texas Rangers in 2010.

The Los Angeles Angels rewarded him with a big payday two years later, but unfortunately, Hamilton wouldn't even play out half of his new contract: Thumb and shoulder injuries which limited him to 89 games in 2014, including an 0-for-13 performance in the ALDS, and a relapse that winter (which Hamilton voluntarily reported to the league) caused L.A. to ship him back to Texas. He would only play 50 more games in the Majors, as a major knee injury required multiple surgeries and sapped what was left of his abilities.

Los Angeles Dodgers - Jason Schmidt
Three years, $47 million

It feels like forever ago, but at one time, Schmidt was one of the best pitchers in baseball, finishing in the top five in NL Cy Young voting in both 2003 and 2004 for the Giants. And because the Dodgers love nothing more than sticking it to their biggest rivals, when they had a chance to sign the almost Cy Young winner, they jumped at the chance. 

The Dodgers gave Schmidt a three-year deal worth $47 million prior to the 2007 season. Their reward for that commitment? A whopping 43 innings: Schmidt landed on the IL with a shoulder injury after just 10 starts, kicking off a saga that would require multiple surgeries and keep the righty on the shelf for the better part of two years. He attempted a comeback in 2009, but he was a shell of himself, allowing 11 earned runs in 17 innings pitched before retiring from baseball.

Miami Marlins: Wei-Yin Chen (five years, $80 million)

Chen seemed to be the epitome of a mid-rotation starter, convincing the Marlins to hand him the largest contract in franchise history. But the Taiwanese-born lefty was below-average throughout the length of the deal, and was a straight-up calamity at the end of it: After three years, one Tommy John surgery and a 4.75 ERA as a starter, the Marlins moved Chen to the bullpen in 2019, where he posted a 6.59 ERA across 45 appearances.

Hard decisions were coming for prospects and roster spots for the Marlins in 2020, and they decided to designate Chen for assignment to protect the roster spot he was holding. He was eventually cut from the team, and the Marlins had to pay his $22 million salary.

Milwaukee Brewers: Eric Gagne (one year, $10 million)

It’s hard to call a one-year deal the worst contract in franchise history, but we need to talk about this Gagne situation. Once arguably the most dominant pitcher on the planet, elbow and back injuries in 2005 and 2006 took their toll, and the Dodgers let him go that winter. After an up and down first half with the Rangers, he was eventually traded to the Red Sox to serve as the setup man for Jonathan Papelbon, a job that he pitched himself out of by the time the playoffs rolled around.

What did the Brewers do with all that very obvious evidence of decline? They gave him $10 million. Not only that, but they made him the closer from day one. Unsurprisingly, it didn't work: Gagne blew his first save opportunity of the season and would lose his closer’s job by early May, giving up 11 home runs in 46.1 innings on the year. There have been more significant misses for Milwaukee, but none more baffling.

Minnesota Twins: Ricky Nolasco (four years, $49 million)

Once again, you’ll hear those fateful words from a small-market team: largest free-agent deal in franchise history. It's never a good sign, especially when the player in question wasn't very good to begin with and just turned 30 years old.

But the Twins were trying to get things together after sliding down the AL Central standings for a few consecutive seasons, and so Nolasco got nearly $50 million guaranteed. He was immediately bad and only got worse, putting up a 5.33 ERA in year one and a 6.75 ERA in year two before being traded to the Angels in 2016.

New York Mets: Jason Bay (four years, $66 million)

This one is still a head-scratcher. Bay had established himself as one of the game's most consistent hitters over his first seven seasons in the Majors, with a 131 OPS+. And he was coming off a successful season with the Boston Red Sox, showing he could play under bright lights.

He should've been a can't-miss player, but the Mets missed hard: Bay suffered a concussion during an outfield collision in his first season in Queens, and whether due to injury or something else, he was never the same player, hitting just .234 with 26 total home runs over the next three years. After that, the Mets decided they'd seen enough, with new Mets GM Sandy Alderson buying Bay out of the final year of his contract.

New York Yankees: Jacoby Ellsbury (seven years, $153 million)

This is a textbook case of a rival living rent-free in your head — and making a legendarily bad decision because of it. Ellsbury was a wildly inconsistent player in Boston, putting up 32 homers in an MVP-caliber 2011 season and failing to even crack double-digits over the rest of his seven years with the Red Sox. But he was a royal pain in the Yankees' side during Boston's World Series runs in 2007 and 2013, and so a floundering Brian Cashman responded by handing him a massive bag that offseason.

Surprisingly enough, an inconsistent and injury-prone player was ... inconsistent and injury-prone in New York, missing significant time in two of his first four seasons with the Yankees while hitting just .264/.330/.386. From there, the injuries really set in: first to his back, then his hip, then a foot ailment, the latter of which caused the team to take the outfielder to court in an attempt to void the end of his deal. Eventually, Ellsbury got his money, while New York was back to the drawing board.

Oakland Athletics: Billy Butler (three years, $30 million)

The Oakland Athletics are famous for hardly ever spending money; Hollywood literally made a movie about it. And when the money is always that tight, every multi-year contract has to work. Unfortunately for Oakland, the Butler deal very much did not: Despite the Royals' run to the World Series in 2014, Country Breakfast was coming off a career-worst year at the plate, and things didn't get any better with a change of scenery.

Butler more or less copy and pasted his line from the previous year in 2015, putting up just a .390 slugging percentage. And things got so much worse in 2016, as a bad season at the plate spiraled out of control when he sustained a concussion from a clubhouse fight with teammate Danny Valencia. Butler was released in the middle of the season and saw his career end that winter despite being just 30 years old.

Philadelphia Phillies: Taijuan Walker (four years, $72 million)

The Phillies were looking to solidify their rotation behind Zack Wheeler and Aaron Nola two offseasons ago. Philly fans wanted a bigger name, but instead they got Walker, who had just enjoyed a bounce-back contract year with the rival Mets. The contract shocked many when it was signed; a $72 million dollar deal and four years from a legit World Series contender?

Spoiler alert: it didn’t work out. After a fine first season, Walker’s ERA ballooned to over 7.00 in 2024 across just 15 starts and 19 total appearances. The righty allowed more than 100 hits, and his WHIP was 1.72. It was a dreadful showing. 

So bad, in fact, that Walker deleted his social media accounts, and multiple reports have speculated that he’s thrown his last pitch in Philadelphia, especially after the trade for Jesus Luzardo gave Philly a full starting five. That’s why we’re comfortable putting this on the list with two seasons left. 

Pittsburgh Pirates: Derek Bell (two years, $10 million)

Bell had enjoyed a fine big-league career, but he only had one truly great season with the Astros in 1998 ... a full two seasons prior to this deal. He did have a decent one-year stint with the New York Mets in 2000, but he missed their run to the World Series with an ankle injury.

It should've been a red flag that the Mets made no effort to re-sign their right fielder. Bell was dreadful in his first (and, it turns out, only) year in Pittsburgh, hitting .136 as late as May and eventually getting sent down to the Minors. The situation hit rock bottom in Spring Training 2002, when Bell responded to having to compete for the starting right field job by telling media members that wasn't going to “go out there and hurt myself in spring training”. He was released not long after, ending his MLB career.

San Diego Padres: Eric Hosmer (eight years, $144 million)

The Padres have been big spenders in the past few years, which can backfire tremendously: Josh Johnson has a really good claim to this list, never even pitching an inning for San Diego, while the current Xander Bogaerts contract already has the makings of disaster.

But even still, Hosmer’s deal was so beyond bad that it might be one of the worst deals in this sport’s history. Outside of a fluky hot streak during the COVID-shortened 2020 season, the first baseman didn't look anything like the player he was in Kansas City, posting a .737 OPS while making a shocking number of errors in the field. He hit just 12 homers in 151 games in 2021, then hit eight in 2022 before San Diego finally gave up and dumped him to the Red Sox, agreeing to pay $12 million of his salary in the process.

San Francisco Giants: Barry Zito (seven years, $126 million)

Barry Zito had a sensational start to his career, winning AL Cy Young honors in just his second full season while forming a three-headed monster atop the A's rotation alongside Mark Mulder and Tim Hudson. By the time he hit free agency, though, the shine had worn off: While the lefty was among the most reliable workhorses in the league, his stuff had begun to diminish, and he posted a 110 ERA+ over his final three seasons in Oakland.

Despite all that, the Giants paid up to poach him from their Bay Area rivals anyway ... and quickly lived to regret it. Zito was awful in year one based on his contract’s standards, and he was awful just by baseball standards in year two, losing a league-high 17 games with a 5.15 ERA. To San Francisco's credit, they kept giving it the ol' college try, keeping Zito in the rotation for almost all seven years of this deal. Unlike many of these contracts, the Giants just paid the man and sent him out there night after night, and they took the results they got, no matter how bad they were. 

Seattle Mariners: Chone Figgins (four years, $36 million)

The Seattle Mariners were aware of the impact Chone Figgins had on a baseball game. As the Los Angeles Angels division rival for the entirety of his eight-year career, he was able to make a huge impression on their front office. At the time of his signing, Figgins had played 108 games against the Mariners, in which he attempted 44 steals. He was pure chaos against Seattle.

So the Mariners signed him for four years and $36 million before the 2010 season. His impact immediately plummeted. After finishing 13th in WAR in 2009, in the same conversation as guys like Derek Jeter and Roy Halladay, Figgins’ WAR plummeted to just over 1.0 in 2010. He played most of a full season, but his eye got worse and he did nothing as far as clutch hitting.

Figgins would lose his starting spot to Adam Kennedy in year two of the deal as he was hitting .188 on the season. They tried to forget the 2011 season and made him a starter again in 2012. Not only that, but they put him back at leadoff where he thrived with the Angels. He was taken out of the starting lineup by May.

Figgins was designated for assignment in November 2012, and his contract was terminated. Figgins sat out a year from baseball before signing a one-year deal with the Dodgers. He was a fine utility man off the bench, but that would end up being his last year.

St. Louis Cardinals: Dexter Fowler (five years, $82.5 million)

Another team that let a player's success with a rival talk them into an ill-advised contract, the Cardinals signed Fowler away from the Cubs, where the outfielder had been wildly successful over the previous two years. But it turned out that Chicago was all too happy to let the 30-year-old go: Fowler made the All-Star team in his first season in St. Louis, but the bottom fell out from there, hitting under .200 with just eight homers in 90 games amid an injury-plagued 2018 campaign.

Fowler wasn't quite so bad over the next two years, but he was nowhere near what the Cardinals paid for, and they dumped his contract on the Angels ahead of the 2021 season. His one season in L.A. was cut short after he tore his ACL sliding into second, and after one more attempt to catch on in Toronto, his career was over for good.

Tampa Bay Rays: Pat Burrell (two years, $16 million)

There are so many “he played there?” moments in Tampa Bay (Devil) Rays history. Jose Canseco tried to revive his career at the Trop. Fred McGriff had a very famous run with the Rays in the late '90s. Wade Boggs signed with the team prior to their inaugural season, recording his 3,000th hit in Tampa.

But the strangest, and the worst, might be the team's signing of former Phillies legend Pat Burrell. Burrell had been a hero of the Phils' consecutive NL pennants in 2008 and 2009, and the Rays felt confident that he could handle full-time DH duties entering his age-32 season. Unfortunately, Burrell never played like it: He hit just .221 in 122 games in his first season in Tampa, and things got even worse in his second year, prompting the Rays to designate him for assignment in May. It doesn't help that he was then picked up by the San Francisco Giants, where he was a crucial piece of a postseason push.

Texas Rangers: Chan Ho Park (five years, $65 million)

The Rangers thought they found a solution to their pitching woes with Park, an All-Star with the Dodgers in 2001. And while this contract paid the righty more than Pedro Martinez and Greg Maddux, it would be worth it if he pitched like he did in L.A.

Instead, Park went 22-23 over the course of this contract, with an ERA of 5.79. Injuries were the main reason for his ineffectiveness, but he just never adjusted to his role as the top guy in the rotation. Some scary medical issues surrounded the rest of his career, and Park never truly recovered from the disaster that was his Rangers tenure. 

Washington Nationals: Stephen Strasburg (seven years, $245 million)

A cautionary tale if ever there were one. A homegrown superstar, Strasburg saved his best year for his contract year, pitching to a 3.32 ERA while leading the NL with 209 innings and helping the Nats capture a World Series title in 2019. With Scott Boras as his agent, you knew the righty was set to cash in, and cash in he did, signing a $245 million deal that was the second-biggest ever given to a pitcher (behind only Gerrit Cole that same winter).

Unfortunately for everyone involved, injuries would completely derail Strasburg's career. He would make just eight more starts over the next three seasons due to complications from a shoulder issue, eventually retiring from baseball in April of this year and years of painful comeback attempts.