Last Wednesday, the marathon was completed.
Fans checked in for Spring Training in February, celebrated Opening Day in March, built a love-hate relationship with their team all summer, and then watched the Milwaukee Brewers win their first-ever World Series in October. Now, it’s time to start the process all over again.
But that process will look a lot different this winter. In fact, this may be the most important offseason in Major League Baseball’s 150-year history.
Here’s everything you need to know as we head into this apprehensive, monumental offseason.
The Impending Lockout
On the morning of Dec. 2, baseball will shut down.
For the first time in 32 years, baseball is attempting to implement a salary cap. It has never been enforced, making MLB the only sports league in North America without one.
The current Collective Bargaining Agreement expires at midnight on Dec. 1. The CBA is baseball’s sole governing contract and determines everything from player contract structures to postseason format. It expires and is renewed every half-decade or so.
Immediately after Dec. 1, Major League Baseball, represented by all 30 team owners, league executives and club officials, will inflict a lockout. This will freeze everything from free agent signings to access to club facilities.
The purpose is leverage. The league is pushing the MLB Players Association to agree to a new salary cap (and floor) system, and it will not be pretty.
The last time the owners pressed for a cap, it almost killed baseball entirely. It happened during the 1994 season, when the players unhesitatingly disagreed and went on strike. It lasted 232 days, from August to April and canceled a World Series.
This was very detrimental to the sport. The strike cost baseball the fans’ support and trust, and once it returned, it was never the same. Stadium attendance and TV viewership plummeted. It even played a key role in the death of the Montreal Expos, who had a winning club in ‘94 but imploded thereafter.
And now it’s time to do it all over again. The big question this time is how long it will last. There’s a grave chance it affects the 2027 season, with real potential for missed games.
That said, clubs have one month to sign free agents without being affected.
Free Agent Market
Buckle up for the next 28 days. With the uncertainty of how long the lockout will last, teams will be aggressive in November while they can.
Like this offseason, the free agent class is also unusual. Many players’ agents have avoided ending contracts right now in fear of the lockout, so few superstar, franchise-altering players are up for grabs.
However, there is one: two-time Cy Young winner Tarik Skubal. He’s been the premier starting pitcher for the last three seasons and won consecutive AL Cy Youngs in 2024 and 2025. If he signs before the lockout, Skubal could become the highest-paid pitcher of all time.
Skubal leads the starting pitchers, the strongest group in this free-agent class. Other notable names include Michael King, Freddy Peralta, Sonny Gray and new Japanese transfer, Kaima Taira.
Taira is one of three star players coming from Japan’s Nippon Professional Baseball league. He has a career 1.78 ERA in his eight years with the Saitama Seibu Lions.
Taira’s market will be lively, but a different Japanese slugger is the prize asset. Meet Teruaki Sato, a 27-year-old power-hitting third baseman. Sato is a five-time NPB All-Star, won the 2025 Central League MVP and is coming off a Triple Crown season.
Because of the smaller market, Sato may be the best hitter available. The other best bats available include Seiya Suzuki, Luis Arraez, Randy Arozarena, Jake Bauers and Jazz Chisholm Jr.
Adrian Morejon and David Bednar highlight the reliever market. However, Bednar, among eight other players, received qualifying offers from their clubs to return for one more season. Of the players aforementioned, Suzuki, Arozarena, Bauers, Morejon and Bednar all have until Nov. 17 to accept or decline.
A Winter To Remember
Some rumors around the league are starting to permeate. That said, expect a flurry of deals to begin by the second week of November.
As of Nov. 3, four clubs seem to be invested in Skubal. The Los Angeles Dodgers, who traded for him at the 2026 Trade Deadline, the New York Mets, Chicago Cubs and New York Yankees.
While the Mets and Dodgers have the checkbooks to rule, don’t sleep on the Cubs. A lot of pieces from Chicago’s rotation are hitting free agency, and Skubal could be a great band-aid – and an expensive one at that.
A few trade speculations have begun, too. The Tampa Bay Rays could seek to deal starting pitcher Drew Rasmussen, since his final year under contract is 2027. If a free agent, Rasmussen would be at the top of many teams’ lists.
Reports also suggest the Baltimore Orioles could open shop after another disappointing season. They may have begun the overhaul at August’s Trade Deadline, sending catcher Adley Rutschman to the Boston Red Sox.
A Ketel Marte trade is also up for real discussion. Marte’s relationship with the Arizona Diamondbacks severely weakened in 2026, and the club even began entertaining a trade last year.
Through all the entertaining rumors of player movement, the undeniable defining feature right now is the lockout. Whether an agreement comes sooner than expected or lasts well into 2027, this offseason will be historic.
Major League Baseball is at a climax. The sport is actively competing with the National Basketball Association for engagement, something that hasn’t happened in decades. International attention is growing, and the sport as a whole is thriving.
The future of baseball will be decided in a couple of months, and we’ll all get a front-row seat.
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