It’s a mere formality Tarik Skubal will reset the standard for highest-paid pitcher in Major League Baseball. And deservedly so.
Skubal posted two of the most dominant seasons in recent baseball history in winning consecutive Cy Young Awards in 2024 and 2025. The left-hander doesn’t turn 30 until next week. Viable starting pitchers are running shorter in supply every year, and the cost for the highest-end talent continues rising.
Topping Yoshinobu Yamamoto’s 12-year, $325 million pact (and Gerrit Cole’s nine-year, $324 million record for a player drafted and developed in the USA) will happen soon, almost certainly before Major League Baseball shuts down the industry Dec. 1. Skubal is slated for meetings with a handful of teams next week, most notably the Los Angeles Dodgers, who acquired him at the August trade deadline for a championship run that ended in the National League Championship Series.
But Skubal will join the $300 million ($400 million?) pitcher’s club toting an injury history a little more extensive than the average mega-ace. He famously had Tommy John surgery in April 2016 while pitching at Seattle Pacific, recovered and was shrewdly drafted by the Detroit Tigers in the ninth round in 2018.
Just as he was evolving into a potential ace in August 2022, Skubal’s second full season in the majors was disrupted by flexor tendon surgery, which limited him to 15 starts in 2023.
And his bid for a third consecutive Cy Young Award was derailed in May, when he underwent surgery to remove loose bodies from his throwing elbow, undergoing an innovative nanoscope procedure that enabled his mound return in just 32 days – and maintain his value heading into free agency.
A team could regard Skubal’s health history in multiple fashions.
On the positive side: He’s had his Tommy John surgery, albeit a decade ago, and has cleared his other hurdles and remained dominant.
A more negative orientation would revive the bromide that past injury is the greatest predictor of future injury.
Yet what can the 10 largest pitching contracts in major league history teach us about how healthy these elite arms were when they signed life-changing pacts, and how they held up after?
We know this much: Four of the 10 highest-paid starters ever won World Series with the teams that signed them. Two more reached the World Series in the life of their contracts.
And the jury is still out on three contracts just getting started – including one ace waylaid by a major injury.
A look at the 10 largest contracts signed by starting pitchers, and how these deals aged for team and player:
1. Yoshinobu Yamamoto, Dodgers: 12 years, $325 million
Signed: December 2023, age 25
Résumé at time of signing: Three-time Ejii Sawamura winner (Japan’s Cy Young equivalent) and three-time NPB MVP
Pre-contract health flags: Reportedly pitched through elbow pain in renowned high school tournament, dropping him to fourth round of NPB draft. Revised training methods apparently quelled the pain. Dodgers contract contains opt outs after 2029 and 2031 but are pushed back to 2031 and 2033 if Yamamoto undergoes Tommy John surgery or is on the injured list for 134 consecutive service days due to right elbow injury.
Post-contract health: Missed three months in June 2024 due to strained rotator cuff.
Post-contract performance: After 2024 IL stint, he’s been one of the game’s greatest pitchers and a crucial and selfless piece of the Dodgers’ consecutive World Series titles in 2024 and 2025. Two-time All-Star, World Series MVP, 2.61 ERA in 76 starts.
Outlook: The World Series trophies make this deal worth every penny already, with plenty more in the offing. Take his three-year sample into account and Yamamoto has a strong case as the best pitcher in baseball.
2. Gerrit Cole, Yankees: Nine years, $324 million

Signed: December 2019, age 29
Résumé: 2019 AL Cy Young runner-up, major league-leading 326 strikeouts, three top 10 Cy Young finishes, career 10.1 strikeouts per nine innings
Pre-contract health flags: IL stints in 2014 (right shoulder fatigue, right lat fatigue) and 2016 (triceps muscle strain, posterior elbow inflammation)
Post-contract health: Underwent Tommy John surgery in March 2025, a year after missing three months of 2024 season with elbow inflammation. Returned to rotation in May.
Post-contract performance: Won 2023 AL Cy Young Award and finished second in balloting in 2021 while making three consecutive All-Star trips. Has struck out 10.6 batters per nine innings, with a 3.19 ERA and 1.04 WHIP and was Game 1 starter for club that reached 2024 World Series.
Outlook: A nine-year deal for a pitcher is almost guaranteed to invite health woes, but Cole was superb before Tommy John surgery and looked crisp in his get-the-lead-out half-season this year. On balance, deal has been and should continue to be great.
3. Stephen Strasburg, Nationals: Seven years, $245 million

Signed: December 2019, age 31
Résumé: 2019 World Series MVP, three-time All-Star, career 10.6 strikeouts per nine innings, 30-8 record in 2016-2017.
Pre-contract health flags: September 2010 Tommy John surgery, eight IL stints between 2013-2018 (neck, back, elbow, oblique, lat, shoulder, cervical nerve)
Post-contract health: Underwent thoracic outlet syndrome surgery in August 2021, a malady that essentially ended his career.
Post-contract performance: Strasburg made just eight starts from 2020-2022 as he battled direct and indirect effects of TOS. He officially retired in April 2024.
Outlook: An up-and-down health saga for Strasburg reached a sad conclusion, just as he’d reached the apex of the sport with a dominant World Series-winning performance. His talent was so overwhelming and ceiling so limitless that the Nationals re-upped him twice, first a $175 million extension and then the $245 million pact after he exercised an opt-out.
4. Max Fried, Yankees: Eight years, $218 million
Signed: December 2024, age 30
Résumé: Three-time All-Star, 3.07 ERA in eight years with Atlanta, World Series champion
Pre-contract health flags: August 2014 Tommy John surgery, IL stints in 2023 and 2024 for left forearm strain, left forearm neuritis
Post-contract health: Spent two stints on IL, totaling 10 weeks, in 2026 for left elbow bone bruise
Post-contract performance: Other than his bone bruise, Fried has been excellent for the Yankees, posting a 2.83 ERA in 52 starts over two seasons and winning 19 games, earning an All-Star nod, in 2025.
Outlook: He’s been about as good as the Yankees envisioned, and while there’s still six more years remaining, the contract length has more to do with knocking down the average annual value ($27.3 million) for luxury tax purposes.
5. David Price, Red Sox: Seven years, $217 million
Signed: December 2015, age 30
Résumé: Cy Young Award winner, two-time Cy Young runner-up, five-time All-Star, 104 wins, 29.3 WAR in first seven seasons
Pre-contract health flags: One IL trip (strained left triceps) in 2013.
Post-contract health: Missed three months in 2017 due to elbow strain, inflammation. IL trips for wrist (twice) and hamstring.
Post-contract performance: Price was initially the workhorse Boston envisioned, leading the major leagues in starts (35) and innings (230) in winning 17 games in 2016. He was a significant figure on their 2018 World Series championship club, winning 16 games with a 1.14 WHIP and then three more in the playoffs, two in the World Series. He never pitched more than 107 innings in a year again, getting shipped to L.A. in a salary dump tied to the Mookie Betts trade with the Dodgers.
Outlook: Overall, a solid sign that lent credibility and length to the rotation, eventually netting a championship in the second season Chris Sale joined forces in the rotation.
6. Clayton Kershaw, Dodgers: Seven years, $215 million
Signed: January 2014, age 25
Résumé: Two Cy Young Awards and a runner-up finish the previous three seasons, 77 wins, 1,206 strikeouts and a 2.60 ERA by age 25.
Pre-contract health flags: Did not appear on injured list in first six major league seasons.
Post-contract health: Amazingly, Kershaw’s first start under his new deal resulted in his first IL appearance – though the fact it involved a long trip to Australia might have contributed to the inflamed muscle in his back, forcing a five-week absence. That would be a bit of a harbinger: A herniated disc in his back sidelined him 10 weeks in 2016 and a lower back strain cost him six weeks in 2017. He’d hit the IL for back issues in 2018 and 2020, as well.
Post-contract performance: Kershaw put up arguably the greatest season of his career in the first year of the deal, winning 21 games with a 1.77 ERA, throwing a no-hitter and winning his third Cy Young Award. The Dodgers won their first World Series since 1988 in the final year of his deal, the COVID-19 shortened 2020 campaign. His numbers over the life of the contract: 98-30, a 2.26 ERA, 0.91 WHIP, 10.3 strikeouts per nine innings.
Outlook: The deal made Kershaw a Dodger for life, in a sense, and remarkably, he had virtually zero arm problems in that span – brief IL stints for shoulder inflammation and biceps tendinitis. His aching back cost him dozens of starts, but never enough to shut him down for a season nor slow down a career that ended with Kershaw as one of the greatest left-handed pitchers of all time.
7. Corbin Burnes, Diamondbacks: Six years, $210 million
Signed: December 2024, age 30
Résumé: 2021 NL Cy Young winner, five top 10 Cy Young finishes, four-time All-Star, averaged 208 strikeouts, 197 innings his last three seasons before free agency.
Pre-contract health flags: One IL appearance for a strained oblique.
Post-contract health: Underwent Tommy John surgery in June 2025, sidelining him 15 months.
Post-contract performance: Still waiting on that after Burnes headed to the operating table just two months into this deal. He returned this past September and made three starts, and should be poised for a relatively normal 2027.
Outlook: Definitely not what you want. But the dark pragmatist might note that Burnes got his TJ out of the way, and there’s still four years remaining on this deal.
8. Max Scherzer, Nationals: Seven years, $210 million
Signed: January 2015, age 30
Résumé: 2013 Cy Young Award winner, two-time All-Star, 39-8 record, 3.02 ERA, 10.2 strikeouts per nine in final two years before free agency.
Pre-contract health flags: Two very brief absences in 2009, 2012 due to right shoulder strains.
Post-contract health: Four IL stints of one to three weeks in 2017 (neck inflammation), 2019 (back, rhomboid strains) and 2021 (groin inflammation).
Post-contract performance: Consecutive Cy Young Awards in 2016 and 2017, followed by second- and third-place finishes. Posted a 2.75 ERA in 200 starts, striking out 11.8 batters per nine over 1,297 innings. Won World Series championship in 2019.
Outlook: Wow, what a deal. Strasburg’s injury and other breakdowns ended Washington’s run of playoff appearances and Scherzer was traded to the Dodgers in 2021; he eventually ran into back and other problems as he reached his 38th birthday in 2023. But he was virtually perfect for the life of this contract and the Nationals got a World Series title out of it.
9. Dylan Cease, Blue Jays: Seven years, $210 million
Signed: November 2025, age 29
Résumé: Two top five Cy Young finishes, including AL runner-up in 2022, when he led the league in WAR. Led AL in strikeouts per nine innings in 2021 (12.3) and the major leagues in 2025 (11.5).
Pre-contract health flags: No major league IL stints since July 2019 debut.
Post-contract health: Landed on IL for first time in May, missing two weeks with a hamstring strain. Placed on IL in late September with shoulder inflammation.
Post-contract performance: A fine first season in Toronto for Cease, who finished runner-up to Cam Schlittler in AL Cy Young voting after posting a 2.40 ERA, leading the AL in FIP (2.56) and strikeouts per nine (12.7). Walks remain an occasional thorn, as he’s yet to throw a 200-inning season, but Cease has so far been the ace the Blue Jays hoped for.
10. Zack Greinke, Diamondbacks: Six years, $206.5 million
Signed: December 2015, age 32
Résumé: 2009 AL Cy Young winner, 2015 NL Cy Young runner-up, six 200-inning seasons, 48.9 WAR, 3.35 ERA in first 12 seasons. A 19-3 record and 1.47 ERA with the Dodgers in final season before opting out.
Pre-contract health flags: No arm trouble from pitching, but Greinke was sent to the IL with a broken collarbone after taking on Carlos Quentin in a 2013 bench-clearing brawl.
Post-contract health: Greinke maintained his rubber arm rep through the life of the contract, with just an oblique strain in 2016 and a neck strain in 2021 sending him to the IL.
Post-contract performance: Greinke wasn’t as dominant as his brief Dodger stint but remained precise, posting a 1.10 WHIP and walking just 1.8 batters per nine over the life of the contract. The Diamondbacks reached the playoffs in his first year and he started in their wild-card game victory. Two years later, they dealt him to Houston, where he made five playoff starts, including a World Series Game 7 duel against Scherzer. Greinke was a member of the Astros’ playoff rotation in 2020 and during another World Series run in 2021.
This article originally appeared on USA TODAY: Tarik Skubal will smash big-money record. What does history say about the risks?