The expectation is left-hander and two-time AL Cy Young winner Tarik Skubal, far and away the best free agent available this offseason, will sign a record contract before the collective bargaining agreement expires at 11:59 p.m. ET on Dec. 1. Barring a surprise agreement, the owners are almost certain to lock out the players at that time. Skubal is expected to sign before then.
Skubal, 30 later this month, is a Scott Boras client and Boras tends to shatter records, not beat them narrowly. There's a real chance Skubal signs a contract worth more than $400 million in the next two weeks or so. Excluding Shohei Ohtani, who is technically a pitcher but is really a two-way player, here are the largest pitching contracts in history:
Largest pitching contracts in MLB history
| Total Guarantee | Average annual value |
|---|---|
1. Yoshinobu Yamamoto, Dodgers: $325M | 1. Max Scherzer, Mets: $43.3M |
2. Gerrit Cole, Yankees: $324M | 2. Justin Verlander, Mets: $43.3M |
3. Stephen Strasburg, Nationals: $245M | 3. Zack Wheeler, Phillies: $42M |
4. Max Fried, Yankees: $218M | 4. Framber Valdez, Tigers: $38.3M |
5. David Price, Red Sox: $217M | 5. Jacob deGrom, Rangers: $37M |
Something like, say, eight years at $50 million a year would give Skubal a $400 million contract that obliterates the previous pitcher records for total guarantee and average annual value. Several big-market clubs are said to be pursuing Skubal (Blue Jays, Dodgers, Mets, etc.), who is a special free agent as an in-his-prime ace. Conditions are ripe for a record deal.
There is also a chance Skubal goes the Valdez route, or the Bo Bichette/Kyle Tucker route, and signs a short-term contract with a high annual salary. It might only be a small chance, but there is a chance. The Athletic reports the Dodgers prefer such an arrangement with Skubal. ESPN says Skubal has no interest in such a deal, though minds can always be changed.
With that in mind, here are the pros and cons of a high-dollar, short-term contract for Skubal. Keep in mind that such a contract is usually a three- or four-year deal with opt outs, not a straight one- or two-year contract, and Skubal wouldn't necessarily have to use the opt outs to re-enter free agency. He could leverage them into a new contract to stay with his team.
Pros
1. Maximize earnings. Plain and simple, a short-term contract would give Skubal a chance to max out his earnings by making free agency available to him again as soon as next offseason. Go out, have a typical Skubal season in 2027, and perhaps market forces push the demand even higher than it is right now. Remember that, along with a salary cap, there could be a salary floor in the future. Small-market contenders like, say, the Guardians or Rays could throw many millions at Skubal to reach the floor in the future.
2. Chance to set more records. This ties back to the last point. Skubal already set a new salary record for an arbitration-eligible player ($32 million in 2026) and he's positioned to set a new standard for pitcher contracts this offseason. Go back into free agency in a year or two, and Skubal (and Boras) could have a chance to break his own pitcher contract record. The record itself won't be a driving factor in that decision (the money will ultimately decide things), but it would be a nice feather in his cap.
3. Freedom to change teams. Sometimes things don't work out. I don't think Juan Soto expected to miss the postseason in the first two years of his record 15-year, $765 million contract with the Mets. It's entirely possible Skubal could find his next situation not to his liking for whatever reason. Maybe the team doesn't contend, maybe he clashes with the coaching staff, maybe he doesn't like the local breakfast taco options. There could be a million different reasons it doesn't work. A short-term, high-dollar deal would give Skubal an escape hatch and allow him to head elsewhere if things go sideways.
Cons
1. Injury and performance risk. All things considered, Skubal is a pretty safe bet on a long-term contract, though he is a pitcher, and pitchers get hurt. It's what they do. Skubal has had three elbow surgeries, including Tommy John surgery in 2017 and a minor procedure this May. If he gets hurt again, or his performance slips for whatever reason, then he could wind up costing himself in the big picture because he won't be able to opt out and sign a larger deal. A short-term, high-dollar contract will pay him handsomely. He won't struggle to put bread on the table. But injury/performance risk means Skubal could ultimately leave money on the table.
2. Potential salary cap. It is possible the next CBA will include a salary cap, which could limit Skubal's market and earning potential should he go back out into free agency in a year or two (or three). It's not just the cap itself either. MLB has proposed contract limits as part of the salary cap: five years at 15% of the cap for players who change teams, or six years at 16% of the cap for players who remain with their current team. Even if MLB doesn't get a salary cap and instead the competitive balance tax system remains in place with stiffer penalties, that could cost Skubal in the future. This offseason might be his last chance to sign in a truly free market.
