This offseason, MLB free agency has moved at snails pace, with many of the top players still available on the open market. This is due to a wide variety of factors, but one thing is clear. Teams do not want to panic in this thin market and make a bad deal.
Long-term contracts, particularly those that reach nine figures, are historically bad for teams. Players don’t reach free agency until they are around 30 years old, with a lot of their prime already in the rearview mirror.
Of course there are players who continue to perform well into their 30s and make these deals worth it, but most of the time, big-money deal are about adding a player who can impact winning at the beginning of a contract that will later turn into an albatross.
In today’s exercise, I have gone through all of the biggest contracts in baseball and have picked out the worst deals in the sport right now. We will begin with two sets of honorable mentions, before we get to our list of the official worst 15 contracts in Major League Baseball.
Bad But Expiring Contracts: Chris Sale and Patrick Corbin
Our first group of honorable mentions are a pair of left-handed pitchers who are finishing off bad contracts that would have certainly made this list in year’s past.
Patrick Corbin has really tested the theory that any contract is worth it if it is part of delivering a championship. Dating back to when he first signed his six-year, $140 million deal with the Washington Nationals, Corbin pitched to a 3.25 ERA in over 202 innings back in 2019.
Since then, he has been the worst qualified starter in baseball, with an MLB-worst 5.62 ERA over the past four years. Pitcher’s records don’t matter much anymore, but it is worth noting that Corbin has a 27-57 record over that span. Corbin has 10 more loses than Jordan Lyles, who has the second-most losses in Major League Baseball since 2020.
The kicker for Patrick Corbin is that his contract was backloaded, so he is owed a whopping $35 million this season, in his final year with Washington.
Chris Sale is another high-priced pitcher on the final year of his five-year, $145 million deal that he signed with the Red Sox prior to the 2020 season. Sale is owed $27.5 million this season with a $20 million club option for 2025.
Once one of the best pitchers in baseball, Sale has really struggled to stay on the mound over the life of this deal. He has made just 31 starts over the last four seasons, with 20 of them coming in 2023. While he finally was on the mound this past year, Sale pitched to a 4.30 ERA.
The one positive note for Sale is that he struck out 29.4% of the batters he faced in 2023, and his expected ERA of 3.71 and his xFIP of 3.72 were both positive signs. There is a much better chance that Sale has a productive season in 2024 than Corbin, although that assumes health.
Sale’s contract looks a lot better now that he has been traded from the Red Sox to the Atlanta Braves, with Boston eating $17 million in the deal to acquire Vaughn Grissom.
High-Priced Padres: Manny Machado, Xander Bogaerts
We don’t need to spend two much time on this pair of players, as there is every chance that they are both supremely productive for years to come for the San Diego Padres. The reason why they are both worth mentioning is the years left on their deals.
Last offseason, A.J. Preller signed Xander Bogaerts to a 11-year, $280 million contract, which pays him $25 million a season through his age-40 campaign. He then followed that up with giving Manny Machado a new extension that was also 11 years long, but worth $350 million.
Production dipped for both Machado and Bogaerts in 2023, but they were still healthy and graded out as net positives both offensively and defensively. Machado posted a 3.5 fWAR, hitting 30 home runs and driving in 91. Bogaerts posted a 4.4 fWAR and was one stolen base and home run away from the 20-20 club.
These contracts are not bad now, and they might not be bad for the next five years. But once we reach the back-half of these contracts, there is a really good chance these are among the worst contracts in the game.
15. Taijuan Walker and Jameson Taillon
There are couple of selections on this list where we are doubling up the players, because they are on such similar deals. This is the case with Taijuan Walker and Jameson Taillon, who were both overpaid in free agency on four-year deals last offseason.
When you look at Walker’s numbers from last season, and then compare him to what pitchers are making on the market this year, there is an argument to be made that the salary is nearly justified.
Walker made 31 starts and pitched to a respectable 4.38 ERA over 172 2/3 innings pitched for the Phillies in 2023. Now while that is solid production, the fact that the Phillies did not hand him the ball a single time (either out of the rotation or bullpen) across their long playoff run is very telling.
Most back-end starters are making anywhere between $10-14 million in free agency this offseason, so Walker is not significantly overpaid based on that market, but most of those deals aren’t for four years. Still owed $18 million per season over the next three years, the Phillies could have spent that money better.
Everything that was just said about Walker applies to Jameson Taillon, who signed a four-year, $68 million deal with the Chicago Cubs last offseason. Taillon is coming off a worse season than Walker however, as he pitched to a 4.84 ERA in his 154 1/3 innings with the Cubs.
14. Lance McCullers
When you look at how other starting pitchers are getting paid this offseason, Lance McCullers’ contract starts to look at lot better. A five-year, $85 million deal pays McCullers $17 million a season, which is what he will make over the next three years.
If healthy, McCullers is a steal for the Houston Astros on that contract. The if there is the issue though, as McCullers has made just eight starts across the first two years of this deal.
The 30-year-old made those starts during the 2022 season, but had to miss time due to a flexor tendon strain, which would go on to plague his 2023 campaign as well.
After trying to rest and rehab the injury, McCullers eventually got surgery to repair the flexor tendon and remove bone spurs last June.
Hopefully he can return to a clean bill of health in 2024, and might just end up being one of the better contracts in baseball moving forward. Still, when you make just eight starts in the first two years of a $85 million contract, that can’t be considered a good deal.
13. Starling Marte
One year ago, Starling Marte looked to be under a great contract for the New York Mets.
While he did miss 44 games in 2022, Marte was an All-Star, hitting .292/.347/.468, with a 134 wRC+, 16 home runs and 18 stolen bases. Signed to a four-year, $78 million deal prior to that season, Marte looked like a real value add for the Mets.
Unfortunately everything changed in 2023, as Marte was plagued by the same groin injury that he missed time with in 2022, and that he got surgery on in the offseason. The now 35-year-old played in just 86 games and hit .248/.301/.324, with a 76 wRC+.
Always a great base-stealer, Marte was able to take advantage of the new rules to swipe 24 bases in 28 attempts, but athleticism eluded him in a lot of other areas of his game. Marte lost a step when it came to his sprint speed, which showed itself in the outfield where he was worth -6 OAA.
Coming into 2024, Marte’s health and production is a massive question moving forward. With two years left on his deal at $19.5 million per season, Marte has suddenly become one of the worst contracts on the Mets books.
12. Andrew Benintendi
Last offseason, Andrew Benintendi signed a five-year, $75 million deal with the Chicago White Sox. This was the largest free agent contract ever given out by the franchise, which says more about the White Sox than Benintendi.
If Benintendi can return to 2022 production, this contract won’t be too onerous. Fifteen million a season for a starting outfielder is not outlandish on the surface, but it certainly was an overpay based on what Benintendi produced in year one.
The 29-year-old has seen a steady decline in his power over the years, but 2023 marked a career-low .356 slugging percentage and just five home runs. Benintendi also lost nearly 50 points on his on-base percentage, going from .373 in 2022, to .326 in 2023.
Throughout his career, Benintendi has at least been an above-average outfielder, but even that eluded him in 2023. He posted -3 DRS in left field and -10 OAA. When it came to fielding run value, Benintendi was in the 1st percentile, as one of the absolute worst defenders in the game.
There is probably more hope for Benintendi to perform this year than Starling Marte because at least he should be healthy, but Marte gave the Mets one All-Star season and there is only two years left on his deal, not four.
11. Jake Cronenworth
Why did the San Diego Padres decide to give a utility man a seven-year, $80 million deal?
Sure, if Jake Cronenworth mirrored his production from 2021 and 2022, when he finished each season with exactly a 4.2 fWAR, than the contract could be a steal. In reality though, this deal makes it’s way on this list because it was unnecessary.
Last year, Cronenworth was set to make $4.225 million in his first year of arbitration before the Padres threw out that number and gave him the seven-year extension. They still had multiple years of team control on Cronenworth, who would not have hit free agency until he was heading into his age-32 season.
Look at the Jeff McNeil extension from last year and you can see where the Padres went wrong with this deal. McNeil was a year closer to free agency and coming off a batting title when he signed a four-year, $50 million extension with the Mets. The deal includes a $15.75 million club option for a fifth year, with a $2 million buyout.
See the Mets bought out two-to-three years of McNeil’s free agency, not five years.
Then of course the karmic retribution of a bad deal reared it’s ugly head for the Padres in year one of the extension, as Cronenworth had a down year where he hit .229/.312/.378, with a 92 wRC+. He was worth just 1.0 fWAR.
10. Christian Yelich
Speaking of ill-timed extensions, we move on to a former MVP, who signed his extension right before a global pandemic in 2020. I recently wrote an entire article about Yelich as a trade candidate, where I outlined his contract at length.
To summarize, Yelich still had three years of affordable team control when he approached the Brewers about an extension, but Milwaukee wanted to reward him as the face of the franchise.
If Yelich maintained his MVP-level production from 2018 and 2019, he would have been a steal on the seven-year, $188.5 million extension. Unfortunately he has fallen off since then, and has not been quite the same player over the first three years of the deal.
Yelich did experience a resurgent season in 2023 though, where he hit .278/.370/.447, with 19 home runs, 28 stolen bases and a 122 wRC+. He was worth just over four wins according to fWAR, a marked improvement from the 3.7 fWAR he posted combined between 2021 and 2022.
With five years left on his deal at $26 million per, plus a $6.5 million buyout on a $20 million club option and $28 million in deferred money, Yelich is a bad contract for the Brewers.
That does not mean he is a bad player though. And with a better health track record than a lot of these guys, Yelich will be more productive than a lot of the guys on this list.
9. Mike Trout
A healthy Mike Trout is worth as much as any player in the history of Major League Baseball. Unfortunately we can no longer ignore the injuries when it comes to Trout.
Prior to his former teammate Shohei Ohtani signed a $700 million deal with the Los Angeles Dodgers, Trout owned the largest contract in MLB history. A 12-year, $426.5 million contract he signed prior to the 2019 season.
Trout went on to win his third MVP Award during the first year of that deal, finishing the season with a career-high 45 home runs and a 177 wRC+. Trout remained healthy and productive during the shortened 2020 season, but injuries began to take their toll in 2021, when he played just 36 games.
In 2022, Trout blasted 40 home runs, but did so in just 119 games played. Last year, production was down compared to his lofty standards and Trout only played in 82 games.
There is no doubt that Trout can still be an MVP caliber player when on the field, but at 32 years old, there are real questions about how much he will be healthy over the next seven seasons. ‘
Owed $35.45 million a year across the life of the deal, Trout has the chance to become a real albatross for the Angels.
8. Jacob deGrom
Last offseason, Jacob deGrom signed a five-year, $185 million deal with the Texas Rangers. Even at the time of signing, many wondered about the health of deGrom, coming off two injury-plagued years with the New York Mets.
DeGrom looked excellent in six starts with the Rangers to start the season, but their worst fears were soon realized when it was announced that the 35-year-old would need Tommy John surgery.
This would be deGrom’s second TJ operation, having gone under the knife soon after he was drafted back in 2010. Unfortunately for the Rangers, they basically missed a full year of deGrom in 2023 and there is no telling when he will return in 2024.
With all of that said, if deGrom makes a full recovery, he will still be worth every penny for the Rangers. Particularly if he can be a real factor for them come October this season.
7. Carlos Correa
No players health was more scrutinized last offseason than Carlos Correa, who lost out on two contracts that would have been over $300 million due to an old ankle injury that drew the concern of both the San Francisco Giants and the New York Mets.
Correa ended up signing back with the Minnesota Twins on a six-year, $200 million deal, which includes a complicated structure of vesting options that span for four more years and an additional $70 million. Everyone can look at Correa’s ankle as a ticking time bomb, but really the problem last year was solely about his production.
The 29-year-old played in 135 games, but hit just .230/.312/.399, with 18 home runs and a 96 wRC+.
If Correa was signed to one of those $300+ million deals, this contract would be up even higher on this list. However if he can get back to being the same guy he was in 2022 with the Twins, this deal could still turn into a good one for Minnesota.
6. Javier Baez and Trevor Story
These two contracts share a spot on this list because they were signed in the same offseason and were for the exact same dollar amount. Both Javier Baez and Trevor Story signed six-year, $140 million deals prior to the 2022 season.
Across the first two years of their respective deals, neither player has lived up to that contract.
For Baez, the problem has solely been his production. The 31-year-old has hit .230/.273/.361, with just 26 home runs in 280 games played with Detroit. The vibes have just been terrible around Baez with the Tigers, as he has not been the same electric player he was prior the contract.
Meanwhile, Story’s problem has really been health.
After playing in just 94 games due to various injuries in 2022, Story needed surgery on his right UCL in January of 2023, which sidelined him for most of the season. He did make a return in August, but did not play well down the stretch, hitting just .203/.250/.316, with a 48 wRC+.
With four years left on their respective deals, each of these shortstops has time to resurrect themselves and turn the narrative around on their contracts.
5. Carlos Rodon
Another contract that was signed just last offseason, Carlos Rodon’s six-year, $162 million deal looks a whole lot different after his first year in pinstripes.
An injury risk coming into the contract, Rodon made just 14 starts last season and did not pitch well across those appearances. The left-hander was knocked around to the tune of a 6.85 ERA. Rodon allowed 15 home runs in just 64 1/3 innings pitched, for a career-worst 2.10 HR/9.
His strikeouts were down, his walks were up and he posted a brutal 3-8 record. It could have just been one bad year marred by injuries, but this deal is looking rather suspect moving forward.
4. Kris Bryant
Not to sound like a broken record, but all of the top five on this list are here because of health.
For Kris Bryant, injuries have limited him to 122 games played across his first two seasons with the Colorado Rockies.
Bryant signed a seven-year, $182 million deal with the Rockies prior to the 2022 season. In year one of the deal, Bryant played in only 42 games, but did hit .306/.376/.475, with a 125 wRC+.
Last year, Bryant was able to see the field for 80 games, but saw a real decline in his offensive production. He hit .233/.313/.367, with only 10 home runs in 335 plate appearances. Bryant’s defense in right field has really fallen off as well. He posted -7 DRS and -4 OAA last season.
Still owed $27 million in 2024, and $26 million a year for four more years after that, Bryant’s contract has become one of the worst in baseball.
3. Giancarlo Stanton
We have now reached the oldest contract in Major League Baseball. Giancarlo Stanton signed his 13-year, $325 million contract back in 2015, when he was still a member of the Miami Marlins.
In year three of the deal, Stanton won the NL MVP, hitting an MLB-best 59 home runs and 132 RBIs. The Yankees traded for Stanton after his big year and have now had him on their books for the past six seasons.
During his time with the Yankees, Stanton does have three 30+ home runs seasons, but he has been marred by injuries that have limited him to an average of about 105 games per season.
Last year, Stanton looked like he could barely move at times, showing his days in the outfield are probably behind him.
He also struggled mightily at the dish, hitting .191/.275/.420, with 24 home runs and a 89 wRC+ in his 101 games played. Stanton is 98 home runs away from the 500-HR club and has four years left under contract to get there.
Stanton has slimmed down a bit this offseason in hopes of being healthier in 2024. If he can return even to 2022 form, where he hit 31 home runs and had a 116 wRC+, the Yankees would gladly welcome that production.
2. Anthony Rendon
The last two guys on this list where paid coming off winning the 2019 World Series as teammates, and everything has gone downhill since. They also both signed for identical contract figures, inking seven-year, $245 million deals that they are now four years into.
Rendon’s healthiest season in an Angels uniform came back in 2020, when he played in 52 of the Angels 60 games and was actually very productive (152 wRC+). Unfortunately since then he has averaged a shade under 50 games per season over the last three years.
When on the field, Rendon has not been nearly as productive for the Angels either, as both his offense and defense have regressed. This is likely due to the injuries, but Rendon is now long removed from his 2019 season, where he hit 34 home runs and drove in 126.
There very little chance that Rendon can salvage much of this deal with the Angels, but at least he’ll still be attempting to get on the field and play over the next three years. The same can’t be said for the last guy on our list, who was forced into early retirement.
1. Stephen Strasburg
Similar to his former teammate Bryce Harper, the hype surrounding Stephen Strasburg before his MLB debut was at a level few have ever reached before. Strasburg was a sure-thing first overall pick back in 2009 and was immediately one of the most highly-regarded pitching prospects ever.
After 12 electric starts in his rookie season in 2010, Strasburg needed Tommy John surgery. He return in 2011 to make five starts, then became an All-Star in his first full season in 2012.
While he battled some injuries, Strasburg was largely healthy from 2012 through 2019, which was the culmination of all of the promise of his big league career.
Along with Max Scherzer and Patrick Corbin, Strasburg was part of the best trio of starters in baseball in 2019, pitching to a 3.32 ERA over an NL-best 209 innings pitched.
Strasburg’s dominance continued into October, where he was eventually named the World Series MVP after winning both of his starts against the Houston Astros, including a pivotal one in Game 6 facing elimination.
At 30 years old, Strasburg was able to exercise an opt-out clause in his contract to become a free agent at his peak value. In free agency, Strasburg returned to the Nationals on that seven-year, $245 million contract, which includes $70 million in deferred money.
In the four years since signing the deal, Strasburg made only eight starts and pitched just over 30 innings. Last August it was reported that Strasburg planned to retire, but that announcement was never officially made.
Strasburg is not expected to pitch again, yet there is still the matter of coming to a final agreement with the Nationals on the remaining three years and $115 million on his contract before he can officially announce his retirement.