Worst Contract in Every MLB Team's History
By Michael Luciano
Every single MLB franchise has THAT contract. You know, the one that cost an obscene amount of money, brought in a player who severely underperformed, and gave their respective fanbases PTSD whenever the front office targets big names in free agency.
At the risk of triggering a flood of bad memories for every MLB franchise, here's the one deal each team wishes they could have back.
30. San Francisco Giants: Barry Zito
Zito might have played out the length of his seven-year, $126 million contract and contributed to some championship teams, but the Giants didn't exactly get a ton of bang for their buck. After posting a 3.58 ERA while making three All-Star teams and winning a Cy Young across the bay in Oakland, Zito jumped to the Giants, where he posted a 4.62 ERA over seven seasons. He pitched forever and ate up innings, but never reclaimed his Cy Young form.
29. Arizona Diamondbacks: Russ Ortiz
While the nearly unplayably bad Yasmany Tomas, currently in the minors, deserves consideration, at least he clubbed 31 homers one year. A former All-Star with the Braves, Ortiz managed just 28 starts with the Snakes, pitching to a cool 7.00 ERA. He only lasted two seasons in the desert before he continued to struggle elsewhere around the league, and his career was over just five years after signing his four-year, $33 million deal, which was considered sizable at the time in 2005.
28. San Diego Padres: Eric Hosmer
A former Kansas City Royals star, Hosmer signed an eight-year, $144 million deal with the Padres to serve as one of their offensive building blocks. That plan has fallen a the first hurdle, as Hosmer has seemingly forgot how to make consistent contact. With a .259 average and just 40 home runs in two years, San Diego is probably wishing that Hosmer's contract was much less expensive as they start to move into win-now territory.
27. Colorado Rockies: Mike Hampton
Hampton, a former All-Star and Cy Young runner-up with Houston, famously said that he signed with the Rockies because of "the school system in Colorado" instead of the $121 million he was handed. Hampton was chewed up and spit out by Coors Field, as he pitched to a 5.75 ERA in 62 starts as a Rockie, and he ended up getting shipped over to Atlanta just two years into his eight-year deal. But hey, at least he was a good hitter!
26. Los Angeles Dodgers: Jason Schmidt
Schmidt was a three-time All-Star the Dodgers pilfered from the rival San Francisco Giants. Unfortunately for Schmidt, he barely saw the mound over the duration of his three-year $47 million deal due to injury. He made just 10 starts in three seasons for the Dodgers, and wasn't very good when he was active, as he piled up a 6.02 ERA in 43 innings. Looks like he left his heart and command in San Francisco.
25. Pittsburgh Pirates: Derek Bell
The notoriously cheap Pirates have been outspent by the Yankees on Gerrit Cole alone, but Bell's two-year deal is still fresh in the minds of scarred Pittsburgh fans. Bell, who hit 134 homers in an 11-year career, was going to have to compete for the starting right field job after hitting just .173 in 46 games the year prior. When notified of this, he quit the team, was released, and never played in the MLB again. He made $4.5 million for this short and horrible stint. And Pirates fans wonder why they had 18 straight losing seasons.
24. St. Louis Cardinals: Dexter Fowler
The former Rockies starter and Cubs All-Star signed a five-year, $82.5 million deal with the Cardinals, but has yet to perform anywhere close to that price tag over the last three seasons. His 2019 season in which he hit just .238 with 19 home runs in 150 games was painful to sit through at times, and has the Cardinals rueing the day they paid a solid starter/role player life-changing money. Enjoy $34 million more of Fowler over the next two years!
23. Cincinnati Reds: Eric Milton
The Reds learned the hard way how hitter-friendly Great American Ball Park would become. Despite giving up an absurd 43 home runs and posting a 4.75 ERA with the Phillies, the Reds plopped down $25 million over three years for Milton. He repaid their faith by once again leading the NL in home runs allowed in 2005 with 40 and never getting his ERA below 5.17 in three years in Cincinnati.
22. Chicago Cubs: Edwin Jackson
Before he was trying to pitch at least one game for every MLB team, Jackson was given $52 million over four years after the Cubs missed out on Anibal Sanchez. This contract was a dumpster fire from the word go, as Jackson managed just a 5.58 ERA over 58 starts in two seasons before he was moved to the bullpen and subsequently traded to the Braves. Not Theo Epstein's finest hour by any stretch of the imagination.
21. Milwaukee Brewers: Jeffrey Hammonds
Hammonds hit .335 with 20 home runs during his only season with the Colorado Rockies in the days of the shorter fences at Coors Field, where he hit .399 that season. Milwaukee somehow looked past this simple observation and decided to pay a below-average outfielder $21 million over the next three seasons, and he repaid them with a -0.3 WAR in that span.
20. Miami Marlins: Wei-Yin Chen
He can start or relieve, but he can't get hitters out. Chen signed a massive five-year, $80 million contract with Miami after four up-and-down-seasons in Baltimore, but never established himself as a quality starter with the Marlins. He was hurt one year and his ERA was north of 4.75 in every other season despite playing in cavernous Marlins Park. 2019 will almost assuredly be Chen's final season in Miami, and he doesn't have much to hang his hat on.
19. New York Mets: Bobby Bonilla
You know the story by now. Bonilla was bought out by the Mets after an extremely volatile time in New York both on and off the diamond, and he took advantage of a contract loophole that allowed him to take in deferred payments of $1.19 million per year until 2035! The payments started in 2011, and the Mets still have 15 years to go. All of that for 95 home runs in 515 games with the club is not the best return on investment.
18. Atlanta Braves: Bruce Sutter
Somehow, the Braves might actually have an even WORSE deferred money story, as they are paying Bruce Sutter, a Hall of Fame closer who spent his best years with the Cardinals and is credited with popularizing the split-finger fastball, $1.19 million per season since he retired in 1988. And the payments will last until 2021. At the very least, the Braves are sending a pioneer and Hall of Famer a paycheck, which looks less bad than the Mets doing so with a guy like Bonilla.
17. Philadelphia Phillies: Adam Eaton
This is not the slap-hitting Nationals outfielder who terrorizes the Phillies. This was a former pitcher who once got injured by stabbing himself with a knife while trying to remove the shrink wrap from a DVD. Coming off of a season in which he had a 5.12 ERA, Eaton made just 51 appearances with the Phillies, and put up a ghastly 6.10 ERA in those games. Oh by the way, he cost $24 million over three years for those gaudy numbers.
16. Washington Nationals: Jayson Werth
This is a tough one. Werth played more games as a National than for any other team, finished in the top 20 in MVP voting, and was a part of teams that won the division several times over. However, Werth cost $126 million to bring to Washington, and he never ascended past the dizzying heights of "solid." Injuries kept Werth from fulfilling his full potential as a National, and he retired upon the expiration of the contract.
15. Seattle Mariners: Chone Figgins
Figgins, who is on the Hall of Fame ballot for reasons that have not been adequately explained to anyone, came to Seattle from the Angels after an All-Star season in which he led the league in walks and stole 42 bases while hitting .298. The Mariners' new $36 million man struggled to even stay above the Mendoza line, hitting .227 in 308 games while hitting just FOUR home runs and driving in only 61 runs. Even as compared to lackluster Mariners of old, that was hard to watch.
14. Texas Rangers: Chan Ho Park
Before he became more well known for drop-kicking Tim Belcher and explaining a poor start as the result of diarrhea, Park was an in-demand starter that made an All-Star team with the Los Angeles Dodgers in 2001. The South Korean star wilted in the Texas heat after signing a five-year, $65 million deal with the Rangers, as he never posted an ERA below 5.46 with the team. He bounced around as a reliever after his stint in Texas, but never became the starter he was with the Dodgers ever again.
13. Oakland Athletics: Esteban Loaiza
Before Loaiza was sentenced to three years in prison for his involvement in a cocaine operation, he was an overpriced flop with the usually frugal Oakland A's. Loaiza was given $21 million over three years after making his name with the White Sox, but he lasted just 28 starts with the A's, registering a 4.62 ERA in that span. It's also pretty safe to say that he hasn't exactly been crushing it of late in regards to his life after baseball.
12. Los Angeles Angels: Josh Hamilton
This one is more sad rather than an example of funny GM incompetence. Hamilton was given $125 million to join the Angels after winning an MVP and batting title with the Rangers. Unfortunately, Hamilton's demons off the field got the better of him, and it affected his play on the diamond, as he hit just 31 home runs in two seasons as an Angel before dealing with substance abuse issues and undergoing shoulder surgery. He eventually went back to the Rangers and played one more season before calling it quits.
11. Houston Astros: Jon Singleton
Singleton was viewed as a trendsetter by the Astros, as they were going to give their prized first baseman prospect a five-year contract that guaranteed him at least $10 million upon his promotion to the major leagues. Needless to day, he was an all-time bust. Singleton could not hit an off-speed pitch to save his life, and racked up just 14 home runs and a .171 average in two big league seasons before Houston opted for the likes of Yuli Gurriel over him. Smart move.
10. Detroit Tigers: Jordan Zimmermann
The Tigers might have made a solid signing when they added Anibal Sanchez in free agency, but the Zimmermann deal looks worse by the day. Given a five-year, $110 million contract after posting a 3.32 ERA in seven seasons with the Nationals, Zimmermann's ERA ballooned in the American League, never going lower than 4.52, and actually rising over 6.00 twice. Last year, he went 1-13 with a 6.91 ERA, which tells you all you need to know about this deal.
9. Kansas City Royals: Omar Infante
Infante was a light-hitting platoon hitter for over a decade, but that didn't stop Kansas City from doling out $30.25 million and installing Infante as their starting second baseman. The light-hitting, slick-fielding Infante garnered a 63 OPS+ and a .238 average in 3.5 seasons with the Royals, which is certainly not worth $7.75 million per season. While fans stuffed the ballot boxes and almost made him an All-Star, Infante was clearly a massive weight on some pretty good Royals teams, and not many were sad to see him go.
8. Chicago White Sox: Adam Dunn
The Big Donkey is arguably the strongest human being to ever play professional baseball, but the lowlights of Dunn's career were some of the most painful stretches in baseball history. After seven straight seasons of 38 or more home runs, the White Sox broke the bank for Dunn with a four-year, $56 million deal, and he proceeded to only hit 11 home runs his first year and almost set the record for lowest qualified batting average ever at .159 if he didn't miss it by a bunch of at-bats. He rebounded with 41 homers next year, but Dunn's .201 average in four seasons as White Sox DH was barely over the Mendoza line.
7. Cleveland Indians: Wayne Garland
After going 20-7 with a 2.67 ERA for the Baltimore Orioles, Garland was given a 10-year deal for $2.3 million with the Indians back in 1977. After pitching an absurd 282 innings in his first season, Garland's arm was spent and his career never recovered. He averaged just 12 starts per season over the last four years of his contract, putting up an average ERA of 5.28. He remains a campfire story among scared Cleveland executives to this day.
6. Minnesota Twins: Ricky Nolasco
Another example of an average pitcher cashing in on a below-average crop of free agent starting pitchers, Nolasco signed a four-year, $52 million contract with the Twins after coming over from the Marlins and Dodgers. Nolasco never looked comfortable in Minnesota, as his 5.44 ERA in 57 starts proved. While he managed to reinvent himself with the Angels and pitch well, Nolasco hasn't thrown an MLB pitch since 2017.
5. Baltimore Orioles: Ubaldo Jimenez
You could have seen this one coming from a mile away. Jimenez rode an All-Star year in Colorado to a big payday with the Indians, where he quickly returned to being Ubaldo Jimenez. That didn't stop the Orioles from handing him a $48 million contract, and he repaid them by never posting an ERA below 4.11 in four seasons and blowing a postseason game against the Blue Jays. With a 6.81 ERA in 2017, Jimenez's MLB career is pretty much done.
4. Toronto Blue Jays: BJ Ryan
A former All-Star reliever with the Orioles, Ryan started off his career with the Blue Jays by posting a 1.37 ERA and making an All-Star team. Great. However, injuries robbed Ryan of some productive years near the end of his career, and his five-year contract quickly became an albatross, as he pitched in just 90 games over the next three seasons at the cost of just under $10 million a season. Not the most thrifty move by from Toronto.
3. Tampa Bay Rays: Greg Vaughn
The Rays don't have many bad contracts in their history, but Vaughn was a disappointment, especially after he made an All-Star team with the Rays. One of the few big fish free agents to choose Tampa Bay, Vaughn had hit 50 and 45 home runs in the two seasons before he signed with the then-Devil Rays, but never hit more than 28 in his three years with Tampa. He limped to the finish of his four-year, $34 million deal, and was out of baseball just a year later.
2. Boston Red Sox: Pablo Sandoval
The Kung Fu Panda made two All-Star teams and was a key member of the San Francisco Giants during their three World Series runs. Upon arriving in Boston as their big free agent in 2015 under a $96 million deal, however, Sandoval shrunk under the pressure. He played in just 161 games with Boston over three years, struggling with weight and hitting just .237 with 14 home runs. Now he's back in San Francisco, and while not a star, he's a productive member of the lineup.
1. New York Yankees: Kei Igawa
Jacoby Ellsbury and Carl Pavano might have been awful contracts, but at least they gave the Yankees SOMETHING of value. Igawa, a much-hyped pitcher from Japan, turned out to be much more Hideki Irabu than Masahiro Tanaka, as he posted a 6.66 ERA in just 16 MLB games. His lack of velocity and command was frankly astounding, and it cost the Yankees $46 million to bring him stateside. What a waste.