MLB offseason bold predictions: Tarik Skubal breaks records, World Series champ gets a deal, a FA frenzy, more

With the offseason underway, Mike Axisa pulls out his crystal ball and predicts how the winter will go Nov 4, 2026 at 8:45 am ET • 7 min read 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. Skubal's contract is closer to $400M than $300M 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. Tarik Skubal contract predictions: Ace's new deal could break multiple MLB records for a pitcher Mike Axisa Brewers keep and extend Contreras 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. It has been foretold. Astros keep Paredes, trade Peña 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. Keeping Peña and trading Paredes, and installing Carlos Correa at the hot corner, is the sensible move. This bold prediction says the opposite will happen. The Astros will trade Peña and keep Paredes, and figure out their 2027 infield alignment later. Houston needs help up and down the roster, particularly on the mound, and I think the offers for Peña will simply be too great for Flores to ignore. It will be similar to the Kyle Tucker trade two years ago. The Astros don't have to move Peña, but the offers will get to a point where they just can't say no. Braves trade a member of their core On one hand, keeping the offense intact and adding some pitching would be a viable offseason plan for the Braves. On the other hand, can they really run it back with the same offense that flatlined after June 1 and in the NLDS? It might be time to shake things up a bit, and I boldly predict it will happen. Ronald Acuña Jr., Drake Baldwin, Michael Harris II, and Matt Olson aren't going anywhere. No team will take the current version of Austin Riley and the six years (!) remaining on his contract. That leaves Ozzie Albies and I suppose Sean Murphy, though the latter is well into role player status now. Does that make this bold prediction a "the Braves will trade Albies" prediction? Yeah, I guess it does. It feels like things are getting a little stale in Atlanta and it's time to change up a core. Rogers gets a larger contract than Peralta You could argue Freddy Peralta is the second-best free agent starter behind Skubal. You could also argue it's Trevor Rogers, who doesn't have Peralta's pedigree or track record, but has strong under-the-hood performance indicators, the kind that project well into the future and get players paid. So, for this bold prediction, I'll say that Rogers signs a richer deal than Peralta, even though the latter is the more famous player and has been better in their careers to date. It'll be close. I can see Rogers getting something in the $125 million range and Peralta signing for right around $120 million, but, in the end, Rogers will sign for more guaranteed dollars because he's a year and a half younger and teams love nothing more than players they believe have untapped upside. That's Rogers, not Peralta. Teoscar returns to Toronto After the Dodgers swept in the NLCS, there were calls to infuse some youth into the roster, and, honestly, they need it. Fortunately, Los Angeles has one of the best prospects in the game in the precocious Josue De Paula, who was so impressive late in the season. Trading an outfielder to clear a spot for De Paula seems like such an obvious move that I'm not sure this prediction qualifies as bold. Andy Pages and Kyle Tucker aren't going anywhere, which leaves Teoscar Hernández. How about a trade that sends Hernández back to the Blue Jays? It's a one-year commitment, the Blue Jays badly need over-the-fence power, and the fan base already loves the guy. Teoscar to Toronto as what amounts to their George Springer replacement. I boldly predict it. Cubs and Yankees make a trade Every offseason, there are two teams that appear to match up so well that a trade feels inevitable. Last offseason, it was the Brewers and Mets for a Freddy Peralta deal. This offseason, it's the Cubs and Yankees. The Cubs need rotation help and have some young position players to spare (like Matt Shaw). The Yankees need infield help and have starting pitching to trade (like Will Warren). I'm not saying Shaw for Warren will happen or even should happen. I'm just saying Chicago's and New York's trade chips and roster needs align very well, and when that happens, a trade typically comes together. This bold prediction says the Cubs will send a position player to the Yankees for a starting pitcher, with maybe some other pieces involved on both sides. Mariners swap an arm for a bat There are trade rumors involving a Mariners starting pitcher every offseason and there's a good reason for that. They have a lot of really good starters and teams want them. The Mariners currently have Kade Anderson, Logan Gilbert, Emerson Hancock, George Kirby, Bryce Miller, and Bryan Woo lined up for their 2027 rotation. They could keep them all because pitching depth has a way of disappearing, sure, but Seattle needed another bat even before Randy Arozarena became a free agent. This next bold prediction says the Mariners finally trade one of their starters in an arm-for-bat deal. I'll say Kirby, who is two years away from free agency, is the one to go. Gilbert is a one-year rental but the better pitcher. The others all have longer control than Kirby. Sato doubles up Murakami After coming out of the gate so well in April and May, Munetaka Murakami finished right where the pundits expected. He hit .207 and had the highest strikeout rate among qualified hitters, but he also slugged 35 home runs in only 127 games. Hanshin Tigers third baseman Teruaki Sato, who will be posted for MLB teams this offseason, is similar to Murakami as a strikeout-prone lefty with huge power. This bold prediction says Sato will double Murakami's contract with the White Sox (two years and $34 million) because he's a better bet to stay at third base, a position that is barren in free agency, and because Murakami provided proof of concept. He showed that a player with big contact concerns in Japan can indeed succeed stateside, even if it is an eyesore at times. Four years and $68 million for Sato, perhaps with an opt out that makes the $68 million not really $68 million. Seven of our top 10 free agents will sign before Dec. 1 Dec. 1 is of course when the collective bargaining agreement expires and the owners are expected to lock out the players. My final bold prediction says free agents and teams will get out ahead of the potential lockout and sign in November. Players won't want to wait until who knows when to sign and teams will want to lock in contracts so they can be grandfathered into whatever the next CBA brings. MLB free agency tends to be slow-moving. Last offseason, only one of our top 10 free agents signed in November, and that was Shota Imanaga taking the qualifying offer. Only three other top 10 free agents signed in December. The other six signed on Jan. 14 or later. This offseason will be the opposite, I boldly predict. There will be a flurry of activity in November and at least seven of our top 10 free agents will put pen to paper before a potential lockout.