With the Brewers crowned World Series champions, the 2026-27 offseason is underway. We're still waiting for the first significant free agent signing or trade, which isn't unusual less than a week into the offseason. Give it another week or so and the action will pick up.
Before the hot stove really gets burning, here are 10 bold predictions for the 2026-27 offseason. Remember, all geniuses were called crazy at first. Yoshinobu Yamamoto's $325 million deal with the Dodgers is the largest pitching contract in history, and our first bold prediction says Tarik Skubal, this offseason's undisputed No. 1 free agent, will beat that.
Specifically, he'll sign a contract that is closer to $400 million in value than $300 million, which is another way of saying he'll clear $350 million and break Yamamoto's record for total dollars by a good bit. Scott Boras, Skubal's agent, likes to break contract records with room to spare, not just by a tiny bit. Skubal is the best free agent starter since Yamamoto, and the best free agent starter with MLB experience since Gerrit Cole in 2019.
It's a very thin free agent class with few places to (wisely) spend money. The bet here is a team steps up and gives Skubal a record deal. Milwaukee's thing over the last few years has been trading its top players a year before free agency (Corbin Burnes, Freddy Peralta, Devin Williams, etc.) and obviously it has worked for them.
William Contreras is at that point now: he's scheduled to hit the open market next offseason. This next bold prediction says the Brewers will buck that trend and instead sign the World Series MVP to a long-term extension that keeps him in Milwaukee for at least another few years, if not the rest of his career. How does six years at $24 million a pop sound?
That would be $144 million total and the richest contract given to a catcher in the last 13 years, clearing Will Smith's $140 extension with the Dodgers. The World Series champs keep their most irreplaceable player. Every offseason is important, and this one is extra important for new Astros GM Randy Flores, who must figure out what to do with third baseman Isaac Paredes and shortstop Jeremy Peña, both a year away from free agency.
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