The 2026 MLB season has concluded with the Milwaukee Brewers crowned as World Series champions, kicking off the 2026-27 offseason. While the first week is typically quiet, significant activity is expected to begin soon. In anticipation of the upcoming market, a series of bold predictions has been outlined regarding contract values, roster moves, and trade possibilities across the league.
Tarik Skubal is expected to sign a historic contract with the Detroit Tigers. The prediction suggests his deal will exceed $350 million, potentially approaching $400 million, thereby breaking the record for the largest pitching contract currently held by Yoshinobu Yamamoto. Agent Scott Boras is known for securing record-breaking figures for his clients, and Skubal is viewed as the premier free agent starter available, with few teams having the financial flexibility to compete at this level.
The Brewers, known for trading top players before their free agency, may deviate from this strategy with catcher William Contreras. Instead of trading him, the team is predicted to sign him to a long-term extension. A deal worth $144 million over six years would make it the richest contract for a catcher in the last 13 years, surpassing Will Smith's previous record with the Los Angeles Dodgers.
For the Houston Astros, new GM Randy Flores faces difficult decisions regarding third baseman Isaac Paredes and shortstop Jeremy Peña. While keeping Peña and trading Paredes seems logical, the bold prediction is that the Astros will trade Peña. The offers for the shortstop are expected to be too compelling to ignore, similar to the previous Kyle Tucker trade, allowing Houston to address other roster needs.
The Atlanta Braves are predicted to trade shortstop Ozzie Albies. After a season where their offense struggled in the postseason, the team may look to refresh its core. While stars like Ronald Acuña Jr. and Matt Olson are likely to stay, Albies is seen as the most movable piece, signaling a shift in the franchise's long-term direction.
In the starting pitcher market, Trevor Rogers is expected to out-earn Freddy Peralta. Despite Peralta's higher profile, Rogers' younger age and strong underlying metrics make him more attractive to teams seeking long-term value. Rogers is predicted to sign for approximately $125 million, while Peralta will receive around $120 million.
The Los Angeles Dodgers are anticipated to trade outfielder Teoscar Hernández back to the Toronto Blue Jays. This move would clear a spot for prospect Josue De Paula and provide Toronto with much-needed power. For Los Angeles, it is a one-year commitment that allows them to invest in youth, while Toronto gains a familiar face to replace their previous power hitter.
A trade between the Chicago Cubs and New York Yankees is also forecast. The Cubs need rotation help and have young position players to offer, while the Yankees need infield depth and have surplus starting pitching. This alignment of needs and assets makes a deal involving a position player for a starter highly probable.
The Seattle Mariners are expected to trade a starting pitcher for offensive help. With a deep pitching staff, the team can afford to move one arm to acquire a bat. George Kirby is identified as the likely candidate, as he is two years from free agency, whereas other starters have longer team control.
Finally, the market is predicted to move quickly before the collective bargaining agreement expires on December 1. At least seven of the top ten free agents are expected to sign in November to avoid a potential lockout. This represents a sharp contrast to the previous offseason, when most major signings occurred in January, as players and teams rush to secure deals before new labor rules take effect.
