Tarik Skubal is not going to sign a multi year contract extension with the Detroit Tigers from a purely financial standpoint. Even if he’d had interest the time for that was sometime in the past two offseasons, and frankly neither party expressed any real interest in doing so. As the reigning two time Cy Young winner, “the best pitcher in baseball”, and a free agent after the 2026 season. Skubal is in a position to command both the highest dollar value and the highest average annual salary that any pitcher,
has ever received, probably $350 million or more as we demonstrate below.
To figure out how much it would take to sign Skubal to a multi year contract, just skip directly to the top of the list of pitchers’ salaries all time. Look at total dollars and average annual salary (AAV).
While there are no pitchers among the list of MLB’s ten highest total contracts, the most money given to a pitcher is the Dodgers’ Yoshinobu Yamomoto, who signed a contract for $325 million to be paid over 12 seasons, 2024 through 2035. The Dodgers also paid a posting fee of more than $50 million to NPB, the Japanese professional baseball league.
Following is a short list of the ten highest total value contracts given to pitchers in MLB history:
Only two pitchers in MLB history have signed contracts with a total value more than $250 million. (We’re excluding Shohei Ohtani who is much, much more than a pitcher.
Only three pitchers have signed contracts with a total value more than $218 million. Only one of them in the past five seasons, and his salary is spread out over twelve seasons.
Still, Tarik Skubal is expected to command a total value contract that will push the highest numbers ever paid to a pitcher.
While Yamomoto holds the record for the highest total salary, his AAV ranks 51st all time among players in MLB and 15th among pitchers, because it’s averaged over 12 seasons. Whether he will actually pitch 12 seasons remains to be seen.
Following is a chart showing the ten highest average annual value contracts (AAV’s) paid to pitchers in MLB history.
Shohei Ohtani tops the list once again, but we’re going to discount his contract since he was signed primarily as a hitter who can also pitch. Yes, he’s a very good pitcher, too. Ohtani’s total value is adjusted here for deferred salary.
The highest average annual value paid to pitcher(s) was given to two former Tigers, Max Scherzer and Justin Verlander, who received $43,333, 333 salaries. Scherzer signed a three year deal and Verlander two years both with the Mets. The Philadelphia Phillies paid Zack Wheeler $42 million apiece for four seasons. Next on the list, at No 10 overall is Framber Valdez at $38.5 million, on a potential four year contract though the final two years are a player option in 2028 for Valdez, and a mutual option for 2029.
The only contracts that topped $40 million were for two to four seasons, excluding Ohtani. Skubal figures to change that as well.
There is only one contract among those 34M or more with a total value above 245 million, and that is the Yankees’ Gerrit Cole. The next highest is the Nationals’ Steven Strasburg at 35M for 7 years. Both of these deals were signed in 2020. Skubal promises to top both the highest AAV and the total dollar value for a free agent pitcher.
Skubal’s contract as a free agent, and therefore any contract he would sign before becoming a free agent, could threaten to break the AAV record, but only if it turned out to be a relatively short term contract. Think more like 8- 10 seasons at an annual salary above $43.33 million. Not that he is expected to pitch ten more healthy seasons, although he might, but teams like to spread out the term of contracts, assuming the long term risks while deferring salary. The Dodgers have made a policy of long-term deferred money, and with a new CBA coming, the brief window of free agency before an impending lockout might be their last big bite at the deferral apple. For some teams, that could also mean avoiding tax consequences through deferred money as well.
THE COST TO RESIGN SKUBAL
Start at 8 years x 43.333 + or about $350 million. Agent Scott Boras was reortedly dialed in on a $400 million contract, but that was before he needed surgery to remove bone chips earlier this season. $350 million is just the starting point if the Tigers were to make an offer.
REASONS TO STAY IN DETROIT
Skubal has little to gain by signing an extension with the Tigers unless the contract will pay him similar to what he would receive as a free agent one season later. There are a couple of perks in staying with Detroit, though.
- In order to reach free agency, he must survive the season and remain healthy. A serious injury could derail his plans and significantly lower expectations for a free agent contract.
- Commissioner Manfred and MLB owners are poised to shut down the game just as Skubal is set to hit free agency, in their never ending quest for a salary cap, which they know very well the players will never agree to. If it plays out like the last lockout, there will be a signing freeze for much of the winter and into the 2027 season.
- In a related matter, Manfred has suggested that the owners could be looking for an individual salary cap that would affect only the very highest paid players. Presumably, there would have to be some offset at the lower end of the pay scale to get players to accept such a deal. MLB’s initial proposal to the players is that free agent contracts would be limited to five years for players changing teams and six years to remain with their current team. Any new rules may be phased in after a year or so.
- Skubal is familiar with Detroit and the Tigers’ organization. Whether there is enough warmth to tilt the talks in favor of staying with the club is another question. Maybe even enough to break a tie? So far, all signs point to him testing the market.
On the flip side of the coin, the biggest contracts result from a bidding war between the games billionaire owners, each wanting to “win” the contract battle. Skubal’s agent, Scott Boras, very rarely signs extensions that deprive his clients of the free agent experience. His modus operandi is to create leverage in competitive bidding between clubs, not being shy to let owners know – often directly through the media — that they’re being out bid by other owners. He has negotiated some of the richest contracts in sports history.
SERVICE TIME
The highest salary given to a pitcher with five plus seasons of service time was the Dodgers’ Clayton Kershaw, who signed a seven year contract worth $215 million to stay in Los Angeles. After that, Luis Castillo signed a five year contract worth $108 million, an AAV of 21.6 M with Seattle.
Skubal himself has the record for the highest arbitration award at $32 million and that is also the highest AAV given to any pitcher prior to free agency.
There aren’t examples of pitchers signing extensions with just one season left before free agency, or at least not in the range of Skubal’s expectations. Again, no surprise here. He’s going to test free agency.
IF THE TIGERS KEEP SKUBAL
If the Tigers don’t trade Skubal and they are unable to sign him to an extension, they would surely make a qualifying offer in November, still under the terms of the current Collective Bargaining Agreement, which projects to be about $22 million, and he would decline that offer and opt for free agency. Once he signs a contract with a total value of more than $50 million, the Tigers would receive a compensatory draft pick after the first round. So add up the value of Detroit having Skubal for the playoff run and the playoffs, plus the supplemental first round pick, for the Tigers to consider a trade.
THE ELEPHANT IN THE ROOM
There is one critical factor that needs to be addressed, and everyone knows what it is. Pitchers get injured. The highest paid pitchers notoriously seem to wind up getting injured. So when a club signs a player for 8 years or 10 years, they pretty much know that they’re not going to get 8 to 10 healthy seasons of performance. And yet, pitching is what wins championships. Of course, it takes hitting as well, but the quest for front line starting pitching is a feature of every contender, in every off season, and again at every trade deadline.
- Gerrit Cole has made 125 starts as a Yankee, but missed the entire 2025 season with Tommy John surgery and returned in May, 2026 after missing 569 days.
- Steven Strasburg made just 8 starts for the Nationals since signing his $245 million contract
- David Price averaged 24.5 starts for the Red Sox in the first four seasons of his seven year contract, but then just 11 starts in the final three seasons since he was traded to the Dodgers, mainly as a salary dump for LA to get Mookie Betts.
- Corbin Burnes made just 11 starts in his first season of a $210M contract with Arizona
- Jacob deGrom made just 9 starts total in his first two seasons of a four year contract with Texas. He made 30 starts in 2025 as he now enters the final year of the deal at age 38.
- That’s five of the ten biggest contracts. Others on the list have been healthy and mostly productive, but the risk of injuries with pitchers looms large. A small to mid market club could be wiped out with such a large contract on the books and getting no value on the field.
The Tigers gave the 10th largest contract by average salary to Framber Valdez at 38.5 million per season, but that was for just three seasons. The salary is obviously not a deterrent, but the number of seasons at such a high salary is just too rich for them. That is something we could only speculate, but as they didn’t make any aggressive push for an extension, there’s no reason to expect anything but Skubal and Boras testing the free agent market and establishing a new bar for top pitching contracts. Depending on how the CBA negotations turn out, the new ruleset, with a proposed hard cap and floor involved, that bar may never be approached again, but it’s still hard to believe that the players’ union will ever agree to a hard salary cap.
