The minute that MLB free agency begins — and as of Monday, any player on the market can sign with team in the league at any time — the Hot Stove scuttlebutt begins. And this winter, most of that scuttlebutt is focused on Tarik Skubal, not just the clear-cut top option in this class but one of the most fascinating free agencies in baseball history.
Where will he sign? When will he sign? And for how much? We're all still waiting to learn the answer, but as the Skubal sweepstakes begin, ESPN's Jeff Passan has provided a lay of the land that already contains some interesting plot twists.
Expect Tarik Skubal to sign before MLB lockout hits on Dec. 2
The most eye-opening bit of information from Passan comes right at the top: "The expectation is [Skubal] will sign before the Dec. 1 lockout". On the one hand, this is hardly surprising; even setting aside the uncertainty around when the league might reach an agreement on a new CBA and return to business, Skubal is seeking to set a new record for the largest contract ever given to a pitcher, and that might be more difficult in a salary cap environment.
On the other, though, it would seem to cut against the grain for Skubal's agent, Scott Boras, a man who has historically been very comfortable pushing his top clients' free agencies as long as they need to go until he gets the offer he wants. It seems like even Boras is ready for a long, ugly labor fight, one he isn't sure the MLBPA will be able to win. Skubal's best chance at a record payday is to convince a big-market suitor that they can get a jump on the market by diving in now rather than playing the waiting game.
The Cubs are already signaling they're out of the Skubal Sweepstakes
One thing that is extremely not surprising about Passan's report: You can add Skubal to the list of free agents that the Cubs would love to sign ... if only the Ricketts family had the money.
"The Chicago Cubs badly want Skubal," Passan writes. "They also are skeptical that they will be willing to compete at the sort of dollars Skubal is expected to get."
At least Passan is willing to call a spade a spade here and use the word willing. Because really, that's what this is: Tom Ricketts is the billionaire son of a finance titan, and one of the richest teams in baseball absolutely can afford to shell out whatever Skubal's asking price is. They simply don't want to, because it will blow a hole in the budget Ricketts has laid out for Jed Hoyer for 2027 (or, more likely, that it will blow a hole in a capped payroll that Ricketts would love to operate within).
Chicago has several rotation holes to fill with Shota Imanaga, Matthew Boyd and Clay Holmes hitting free agency and Justin Steele, Cade Horton and Ben Brown still working their way back from injury, so perhaps shelling out for Skubal would be a misallocation of resources. Still, it's hard for Cubs fans not to feel disheartened here after so many years of doing just enough to be competitive but not enough to get over the hump.
Could the Padres keep Tarik Skubal in Southern California?
Passan ticks off the usual suspects for Skubal's services, most especially the Los Angeles Dodgers and New York Mets. But he also drops a bit of a surprising name as well: "With Michael King and Nick Pivetta being free agents, the San Diego Padres need a rotation anchor, and arguably the best pitcher in baseball would more than suffice."
The need can't be argued: As Passan notes, San Diego has very little in its rotation currently under contract beyond Joe Musgrove (hasn't pitched regularly since 2024) and Randy Vasquez (a No. 4 or 5 starter at best). And you know they'd love nothing more than to steal a Cy Young winner from their division rival. But with so many huge contracts on the books already, can they really make the money work? An enthusiastic new ownership group certainly helps, but unless Skubal's market really craters, it's hard to see.
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