MLB’s 10 riskiest contracts from 2024 offseason

It was an offseason to remember in MLB. 

The largest contract in sports history was signed, as was the largest for a pitcher — with the same team responsible for both deals. Nearly $4 billion was promised, with 12 teams handing out at least $100 million. The Dodgers alone committed to well over $1 billion in deals. 

With each contract comes great hope and real risk. Some pacts from this past winter were especially curious, from both the team and player sides. Star prospect Jackson Chourio, for instance, signed an eight-year, $82 million deal with the Brewers, and he’s yet to make his MLB debut. 

But that agreement didn’t even make our list of the riskiest contracts from this offseason. Here are the 10 that did.

Biggest team risks

1. Yoshinobu Yamamoto, Los Angeles Dodgers, RHP: 12 years, $325 million

Other contract details: Player opt-outs after the 2029 and 2031 seasons. If Yamamoto suffers an elbow injury at any point from 2024-2029, a $10 million dollar club option with no buyout is added to the end of the contract.

There might not have been a pitcher with better stuff on the open market over the offseason. Of course, there are also a lot of unknowns with the 25-year-old Yamamoto, as he transitions to MLB after claiming every major award (multiple times!) in Nippon Professional Baseball over the past few years. Alas, he’s gotten off to an inauspicious start in the majors, struggling in spring training before lasting just one inning in the Dodgers’ second game with the Padres in last week’s Seoul Series. But Yamamoto was already the headliner for this list the moment he was given such an exorbitant pact — the most for a pitcher in MLB history — before throwing a single pitch in the majors. This is arguably the riskiest contract in baseball history.

2. Jung Hoo Lee, San Francisco Giants, OF: Six years, $113 million

Other contract details: Player opt-out after the 2028 season

Lee was probably unfamiliar to many when he signed with the Giants, though he was a coveted free agent within MLB. The bigger surprise was how much the 25-year-old got. Most projections slotted the Korean Baseball Organization standout to net about half of what San Francisco guaranteed him. Who would have guessed when he signed in mid-December that he’d be just one of four free agents to eclipse $100 million. Now, he’s slated to lead off and play center field for the revamped Giants, and he could be an ideal fit in cavernous Oracle Park. But he’s getting paid nine figures to hit like an All-Star, too. After slugging under .500 in the KBO last year and registering just two seasons with double-digit home runs, his transition at the plate bears monitoring.

3. Tyler Glasnow, Dodgers, RHP: Five years, $136.6 million

Other contract details: Final year in the deal (2028) is a club option for $30 million, but if the option is declined, it converts to a player option worth $21.6 million.

Everyone knows Glasnow’s stuff is electric. The rub is, he often isn’t available to provide it. His 120 innings last year were a career high, as were his 21 starts. At the same time, it’s tough to ignore his career 11.5 strikeouts per nine innings. After trading a mini haul to acquire him from the Rays this offseason, the Dodgers doubled down and gave the 30-year-old Glasnow a four-year extension. If he can remain relatively healthy, he’s a good bet to make good on the deal. But that’s a big if.

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4. Aaron Nola, Philadelphia Phillies, RHP: Seven years, $172 million

Nola has been a workhorse for the Phillies for a while. Thus, he got a contract in line with what frontline starters get. But there are some warning signs with Nola. He turns 31 in June, will be 37 when this deal expires, and has thrown over 1,000 innings since 2018. Moreover, last season was the first since 2019 in which his FIP was above four, while his K/9 also dipped below 10 for the first time in five years. His walks per nine innings also increased above two, nearly doubling his rate from the previous season.

5. Josh Hader, Houston Astros, LHP: Five years, $95 million

Amid all their success over the past decade, the Astros have been especially conservative when it comes to free agency. That made their agreement with Hader all the more surprising. It was the most money guaranteed for a reliever in MLB history. Houston’s acquisition of the former Padres closer also pits him in a late-inning stable with standout duo Ryan Pressly and Bryan Abreu. Such a luxury move is sure to be scrutinized regardless of its success. With that said, the 29-year-old Hader has been lights out for all but one of his six full seasons. The only real concern is with his walk rate. He’s topped 10% in four of the past five years and ranked in MLB’s bottom 5% just two years ago. But if Hader can consistently close out wins for Houston, which has its sights set on more titles during the span of this deal, no other numbers will matter.

6. Shohei Ohtani, Dodgers, DH/RHP: 10 years, $700 million

Other contract details: $680 million has been deferred without interest; Ohtani will earn $68 million per year from 2034-2043.

The risk here is obvious, after Ohtani signed the largest deal in sports history. That the Dodgers are paying him just $2 million annually over the next decade and deferring the other 97% of the deal (without interest) until 2034 softens the hit, especially in real time. But there will still be an astronomical $700 million switching hands between the Dodgers and Ohtani, whose representation shrewdly conceived the unique contract structure. The pact represents a 60% increase from MLB’s previous record contract. But if anyone is worth it, it’s the 29-year-old Ohtani. Baseball’s biggest draw and international icon is coming off his second unanimous MVP award with the Angels and might not yet have reached his ceiling as a hitter. The bigger concern with the two-way star is whether he’ll ever return to form on the mound following a second UCL tear that’s forcing him to strictly DH for the 2024 season. If he were unable to pitch effectively down the road, Ohtani has shown in the past that he can play a solid right field. But that isn’t what the Dodgers are really paying him for. 

Biggest player risks

1. Blake Snell, Giants, LHP: Two years, $62 million

Other contract details: 2024 salary is $15 million with $17 million signing bonus payable by January 2026; player option for the 2025 season worth $30 million. If picked up, $15 million of that option is deferred without interest until 2027.

Welcome to the “Boras Four” section of this list. The expectation heading into the offseason was that Snell, at 31 years old and coming off his second Cy Young, would challenge for the biggest contract of any pitcher in this cycle. That might be why he reportedly rejected a $168 million offer from the Yankees. By late March, Snell had to settle for a two-year deal that allows him to opt out after this season. It will be hard for him to replicate what he did in 2023, when he registered a historic 1.20 ERA over his final 23 starts with the Padres. But after holding out for a better deal and then seeing the money dry up in free agency, the lefty had no choice but to bet on himself in hopes of securing a bigger bag next winter. The Giants and their pitcher-friendly park make for a good match in 2024 (and perhaps 2025). Snell can also help himself by lowering his walk rate, which was the highest in baseball last year, and being more effective with his fastball, which saw opponents post an expected slugging percentage of .500.

2. Jordan Montgomery, Arizona Diamondbacks, LHP: One year, $25 million

Other contract details: Option for the 2025 season vests at $20 million with at least 10 starts made in 2024. The option increases to $22.5 million with 18 starts and $25 million with 23 starts. Montgomery can also opt out before 2025.

After a lights-out second half and postseason with the Rangers that saw Montgomery post a 2.90 ERA, the lefty was projected to land a deal in the range of what Carlos Rodón received last offseason from the Yankees (six years, $162 million). Despite multiple contenders being in need of a high-impact arm, Montgomery’s market never manifested through five months, allowing Arizona to swoop in and nab him on the eve of Opening Day for just $25 million. Woof. While the 31-year-old lefty doesn’t have a lengthy track record of great success, Montgomery was arguably better than he’d ever been to close out the 2023 season. So, another strong campaign could set him up to cash in next winter. Improving some of his peripherals would surely help. Montgomery’s FIP has often been a fair amount worse than his ERA, while his 27% line-drive rate last year was the highest in the majors among pitchers with 180 innings. Moreover, his sinker, four-seam fastball and cutter had expected batting averages of .275, .299 and .371 last season, respectively, so some regression could be coming.

3. Cody Bellinger, Chicago Cubs, OF/1B: Three years, $80 million 

Other contract details: Player opt-out after the 2024 and 2025 seasons. The opt-out in 2025 includes a $2.5 million dollar buyout, while the 2026 opt-out includes a five million dollar buyout. 

Aside from Ohtani, a baseball unicorn if there ever was one, the 28-year-old Bellinger figured to land the biggest deal for a position player this past offseason. He was one of the best stories in baseball last year, earning NL Comeback Player of the Year and Silver Slugger honors in the process. Still, projections were all over the place for the former MVP. He was so bad from 2021 to 2022, and then so peculiarly good in 2023, demonstrating a completely different hit profile than his days with the Dodgers. It was widely assumed he would, at the very least, break the $100 million mark. Instead, he’s promised just $80 million, although he can hit the open market again after either of the next two seasons. Returning to the cozy confines of Chicago and Wrigley Field seems like a safe move, as well. If Bellinger can replicate last year’s slash line (.307/.356/.525) while improving a hard-hit rate that sat significantly below league average, he’ll be positioned for a better bout with free agency next winter.

4. Matt Chapman, Giants, 3B: Three years, $54 million

Other contract details: Player opt-outs after the 2024 and 2025 seasons. The 2025 player option is for $17 million and includes a two-million-dollar buyout. The 2026 player option is for $18 million and includes a $3 million buyout. There is a 2027 mutual option for $20 million with a $1 million buyout.

At two different points in his career, with two different clubs, Chapman reportedly turned down extensions of at least $125 million. But that market simply no longer exists for the former All-Star. Set to turn 31 in April and coming off a good but uneven 2023 with the Blue Jays, some projections had him landing a nine-figure deal this winter. But as his Scott Boras-represented peers can attest, waiting was not the right move in this cycle. Considering what he got from the Giants, it’s likely that Chapman overplayed his hand from the onset of free agency. The good news is, he’s still an outstanding defender and his new deal gives him the flexibility to test the market again should he improve at the plate. Unlike Bellinger, Chapman delivers alluring hard-hit rates and exit velocities. It’s the lack of contact and paltry on-base percentage (.319 over the past four seasons) that has scared teams off. While he’ll have his work cut out for him if he’s going to boost his numbers with home games at Oracle Park, it’s worth noting that his best hitting seasons did come at pitcher-friendly Oakland Coliseum.



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