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Following the Milwaukee Brewers’ World Series championship, the 2026-27 Major League Baseball offseason is officially underway. CBS Sports has outlined 10 bold predictions for the upcoming winter, anticipating landmark contracts, high-profile trades, and an unusually rapid signing pace.
Record Contracts and Extension Plans
Top free agent starting pitcher Tarik Skubal is projected to command a historic contract valued closer to $400 million than $300 million, surpassing the current record of $325 million set by Yoshinobu Yamamoto with the Los Angeles Dodgers. Represented by agent Scott Boras, Skubal stands out as the premier starting pitcher on the open market, which could push suitors beyond the $350 million threshold.
Meanwhile, the champion Milwaukee Brewers are predicted to depart from their typical strategy of trading key talent before free agency. Instead of moving World Series MVP William Contreras, Milwaukee is forecasted to agree on a six-year, $144 million extension, surpassing the $140 million mark set by Will Smith with the Dodgers to make Contreras the highest-paid catcher in over a decade.
Potential High-Profile Trades
Several major roster retoolings are projected across the league:
- Houston Astros: Under new general manager Randy Flores, the Astros are forecasted to trade shortstop Jeremy Peña to acquire pitching help while retaining third baseman Isaac Paredes.
- Atlanta Braves: To revitalize an offense that struggled late in the season, Atlanta is predicted to trade second baseman Ozzie Albies while retaining the rest of its core group.
- Los Angeles Dodgers & Toronto Blue Jays: The Dodgers could clear space for top prospect Josue De Paula by trading outfielder Teoscar Hernández back to the Toronto Blue Jays as a power bat.
- Chicago Cubs & New York Yankees: The Cubs are projected to swap position player talent, such as Matt Shaw, for starting pitching from the Yankees, such as Will Warren.
- Seattle Mariners: Looking to bolster their lineup, Seattle is expected to trade starting pitcher George Kirby, who is two years away from free agency, in exchange for an impactful hitter.
Free Agent Valuations and Lockout Timeline
In the starting pitching market, free agent Trevor Rogers is projected to secure a larger total guarantee than Freddy Peralta—potentially reaching around $125 million compared to Peralta’s projected $120 million—driven by Rogers’ younger age and strong underlying performance metrics.
From international markets, Hanshin Tigers third baseman Teruaki Sato is predicted to sign a four-year, $68 million contract through the posting system. This deal would double the two-year, $34 million contract signed by Munetaka Murakami with the Chicago White Sox, backed by Sato’s defensive fit at third base and proven power potential.
Finally, with the collective bargaining agreement set to expire on Dec. 1, a rapid wave of activity is expected. At least seven of the top 10 free agents are predicted to sign contracts before December to secure terms ahead of a prospective owner lockout.
