With the Milwaukee Brewers crowned 2025 World Series champions, the 2026-27 MLB offseason is underway. A new set of bold predictions outlines potential record-breaking contracts, notable trades, and a possible rush of signings before a potential lockout when the collective bargaining agreement expires on December 1.
Skubal to break pitching contract record
Tarik Skubal, the offseason's top free-agent starter, is predicted to sign a deal closer to $400 million than $300 million, surpassing Yoshinobu Yamamoto's $325 million record for a pitcher. Agent Scott Boras has a history of breaking contract records by a significant margin.
Brewers extend Contreras
Milwaukee is expected to buck its trend of trading stars before free agency by signing World Series MVP William Contreras to a long-term extension. A six-year, $144 million deal ($24 million annually) would become the richest catcher contract in 13 years, topping Will Smith's $140 million extension with the Dodgers.
Astros trade Peña, keep Paredes
New general manager Randy Flores is predicted to trade shortstop Jeremy Peña, a year from free agency, while retaining third baseman Isaac Paredes. The return for Peña could resemble the haul received for Kyle Tucker two years ago.
Braves shake up core with Albies trade
After an offense that flatlined after June, Atlanta is forecast to trade second baseman Ozzie Albies. Ronald Acuña Jr., Michael Harris II, Matt Olson, and Drake Baldwin are considered untouchable, while Austin Riley's contract makes him unmovable.
Rogers out-earns Peralta
Left-hander Trevor Rogers, a year and a half younger than Freddy Peralta, is projected to sign a richer free-agent deal, perhaps around $125 million compared to Peralta's $120 million, as teams value Rogers' perceived untapped upside.
Teoscar Hernández returns to Toronto
The Dodgers are predicted to trade outfielder Teoscar Hernández back to the Blue Jays on a one-year commitment, clearing a roster spot for top prospect Josue De Paula and providing Toronto with needed power.
Cubs and Yankees swap position player for pitcher
Chicago's need for rotation help and surplus of young position players (like Matt Shaw) align with New York's need for infield help and excess starting pitching (like Will Warren), making a trade between the two clubs likely.
Mariners trade a starter for a bat
Seattle, loaded with starting pitchers including George Kirby, Logan Gilbert, and Bryan Woo, is expected to finally move one arm for offensive help. Kirby, two years from free agency, is cited as the most likely candidate.
Sato doubles Murakami's contract
Japanese third baseman Teruaki Sato, set to be posted this offseason, is predicted to sign a four-year, $68 million deal with an opt-out, doubling the two-year, $34 million contract Munetaka Murakami received from the White Sox. Sato's defensive profile at a scarce position and Murakami's proof of concept drive the higher valuation.
Flurry of signings before December 1
With a potential lockout looming when the CBA expires on December 1, at least seven of the top 10 free agents are forecast to sign in November. Last offseason only one top-10 free agent signed before December; this year teams and players are expected to accelerate negotiations to lock in contracts under the current agreement.
