The 2026 regular season ended Sunday, and the winter that follows is the strangest one baseball has faced since 2021. Free agency is about to open with a collective bargaining agreement that expires on December 1 and owners pushing for a salary cap for the first time since 1994. Every deal this offseason is racing a clock.
That backdrop changes how you should read the market. It also makes the answer to the biggest question easier, not harder.
Tarik Skubal is the story, and he is leaving Los Angeles
Skubal is the best player who will hit the open market, and it is not close. He has won the last two American League Cy Young Awards, he set an arbitration record at $32 million in February, and the Tigers traded him to the Dodgers on August 2 for Zyhir Hope, River Ryan and Brady Smith. That trade was a rental, and rentals end.
ESPN’s Jeff Passan has floated a number close to $500 million, which would roughly double Stephen Strasburg’s $245 million record for a pitcher. Passan’s own caveat is the important part: a deal that size means a decade or more, and Skubal turns 30 in November. No pitcher his age has ever been paid anything like that.
He will still get paid, and my read is that the Dodgers are not the ones who pay it. They already have the deepest rotation in baseball and they just spent real prospect capital on four months of him. The Mets and Blue Jays are the two clubs with both the payroll room and the urgency to blow past everyone else, and a December 1 lockout threat gives a player every reason to take the biggest guarantee on the table in November rather than wait for a market that may not reopen until spring.
Skubal’s elbow is the one real risk
He had surgery in May to remove loose bodies from his left elbow and missed roughly six weeks before returning on June 13. He pitched well when he came back. Any front office committing half a billion dollars is going to spend a long time with those medicals, and that is the single most likely reason the final number lands well short of the projections.
Who else actually moves
Behind Skubal, the class is more useful than it is thrilling. Randy Arozarena is the best bat available after five straight seasons of 20 homers and 20 steals for Seattle. Luis Arraez remains one of the purest hitters in the sport, with defensive questions that have followed him to every stop, and the Yankees have an obvious hole at second base. Kevin Gausman, Michael King and Freddy Peralta give teams rotation options that will not require a decade of commitment.
The trade market may be busier than free agency
If owners lock the players out on December 2, signings stop but trades of players already under contract can still be negotiated once a deal is struck, and clubs have been laying groundwork all September. MLB.com’s list of candidates is heavy on controllable talent: Jeremy Pena entering his walk year in Houston, Steven Kwan a year from free agency in Cleveland, Logan Gilbert in the same spot in Seattle, and Spencer Strider with two years and an option left in Atlanta.
Those are the names that will actually swap uniforms in volume. Skubal is the name that will define the winter, and when he signs, he signs somewhere other than Los Angeles.
A longtime sports reporter, Carlos Garcia has written about some of the biggest and most notable athletic events of the last 5 years. He has been credentialed to cover MLS, NBA and MLB games all over the United States. His work has been published on Fox Sports, Bleacher Report, AOL and the Washington Post.