15 bold MLB offseason predictions just crazy enough to come true

Every year, it feels like we know what'll go down in the MLB offseason, only to be surprised by what actually happens. For example, who in the world had Corbin Burnes signing with the Arizona Diamondbacks of all teams? Juan Soto to the New York Mets wasn't outlandish by any means, but for $765 million? Did anyone really expect the Los Angeles Dodgers to sign Tanner Scott and Kirby Yates? It's important to be bold when making offseason predictions.

No, I don't mean projecting that Kyle Tucker will sign with the Pittsburgh Pirates — this isn't MLB The Show — but thinking outside of the box with a hint of realism might result in predicting what will end up going down this winter. With that in mind, let's take a look at the offseason calendar and make some bold, yet somewhat realistic predictions.

What to expect this MLB offseason

1. Full MLB offseason calendar
2. MLB free agency bold predictions
3. MLB offseason trade/extension bold predictions

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Full MLB offseason calendar

Free agency has technically begun, but free agents can only negotiate with their own teams until Nov. 6. On that same day, we'll see official contract options revealed, and which players will receive the qualifying offer. A week of award announcements will then lead to GM meetings, a period of time that typically doesn't involve much action, but has tons of rumors to comb through.

A week or so later, we'll see which players are willing to accept qualifying offers and which players will be non-tendered, allowing them to hit free agency earlier than otherwise expected. A week into December is typically when the real fun begins, as the Winter Meetings take place in Orlando, Florida. Players can, and will, sign before the Winter Meetings, but the Winter Meetings are usually around when the best players make their decision.

Now that you know around when the action will happen, here's a look at some bold, yet fairly realistic predictions.

MLB free agency bold predictions

Kyle Schwarber nets six-year deal from Phillies

Kyle Schwarber re-signing with the Philadelphia Phillies is far from bold, but for six years? That's bold, yet fairly realistic. Is signing a soon-to-be 33-year-old DH who strikes out a ton, doesn't run well, and is coming off by far his best season to a six-year contract a good idea? Maybe not, but it feels like Schwarber has all the leverage here.

If he walks, what's the Phillies' alternative? How can they seriously say they have a better shot to win it all in 2026 if they don't re-sign the likely 2025 MVP runner-up? And it's not as if Schwarber, even as a DH, will have a shortage of suitors. I don't know how many suitors would give him a long-term deal, but there's likely to be at least a couple of those. He just hit 56 home runs and is showing no signs of slowing down.

Michael King returns to AL East, but not with Yankees

Michael King is underratedly one of the best starting pitchers available. His 2025 season didn't go as planned as he was limited to 15 starts due to injury, but he had a 2.59 ERA in his first 10 starts before his injury woes, and he had a sub-3.00 ERA in 31 appearances (30 starts) in 2024. He doesn't have a massive track record when it comes to being successful as a big league starter, but he certainly has immense upside.

The New York Yankees figure to show some level of interest in reuniting with King, but I predict he ends up with an AL East team that isn't the Yankees. The Toronto Blue Jays, Boston Red Sox and Baltimore Orioles could all use starting pitching, and King won't break the bank, making him an ideal fit for all three of those teams.

Pete Alonso has repeat of 2025 offseason, but gets more security from Mets

Pete Alonso's free agency dragged on until February last offseason, when he re-signed with the New York Mets. I don't think it'll take him quite as long to sign this offseason, but I do think it'll be a similar experience. I expect Alonso's free agency to drag on, and I expect that at the end of the day, he'll sign an awfully similar deal with the Mets, albeit with an extra couple of years of security.

Alonso is reportedly looking for a seven-year deal, but how likely is it that a first baseman on the wrong side of 30 who happens to also be a very poor defender and base runner ends up with that long a deal? With Scott Boras representing him, it'll likely be a while before Alonso is willing to adjust his demands. I don't expect Alonso to have a massive seven-year deal on the table, but with no qualifying offer and with the first baseman coming off a much better year in 2025 than he was in 2024, I do think a four or five-year deal is realistic. The Mets might not love that length, but with a lack of alternatives, they can't really afford to let Alonso walk.

Yankees don't take Kyle Tucker pursuit seriously, pursue outfield help with trade

What the New York Yankees should do after their early postseason exit is go all-out for Kyle Tucker, the best free agent available. Tucker might not be Juan Soto with the bat, but he's a much better defender than Soto and still a superstar hitter. Adding him to an already formidable Yankees lineup could make them the favorites to get back to the World Series in 2026. With that being said, it's hard to trust that the Yankees will fork over the near $400 million it'll take to sign Tucker.

Time and time again in recent years, the Yankees have passed on the biggest of names and settled on a less expensive alternative. Why won't that play out here with Tucker and another player like Steven Kwan? Everyone knows Kwan isn't the player Tucker is, but he's a very good player coming off a very good year with the Cleveland Guardians, doesn't strike out, is a terrific defender, was on the trade block and will be significantly cheaper. While Hal Steinbrenner is willing to spend money, he has clearly defined limitations. It's hard to see him green-lighting Brian Cashman to go above and beyond for Tucker, but trading prospects for a cheaper Kwan makes sense.

Dylan Cease gets richest starting pitcher contract

Dylan Cease is coming off a down year, which saw him post a 4.55 ERA in 32 starts for the San Diego Padres. Fans who think their team can sign the right-hander to a bargain deal should think again. It might be a bit of a stretch to predict that Cease will make more than guys like Framber Valdez and Ranger Suarez, but I'm going there.

Cease has been inconsistent in recent years and walks too many, but he has five straight seasons of 32+ starts, 165+ innings and 210+ strikeouts, and has finished in the top four of the Cy Young balloting in two of those five years. Cease is as reliable as anyone when it comes to simply taking the ball every fifth day, and he has legitimate Cy Young upside while also only turning 30 years old in December. Teams value reliability and upside, and there's no better option on the market than Cease in both of those categories.

Bo Bichette re-signs with Blue Jays for less than Tigers offer

Bo Bichette's free agency market should be fascinating. He isn't a good defender and probably shouldn't be at shortstop, but he's an unbelievable hitter who has had at least 175 hits in four of his last five seasons. Despite missing much of September due to injury, Bichette finished tied for second in the majors in hits while also leading the majors with a .381 average with runners in scoring position. He is a star hitter, and the fact that he's voiced a clear desire to play the rest of his career alongside Vladimir Guerrero Jr. in a Toronto Blue Jays uniform cannot be ignored.

The Detroit Tigers could desperately use help in their infield and should throw a ton of money in Bichette's way, but how willing will Bichette be to leave the Blue Jays? Last offseason, we saw a different free agent, Alex Bregman, turn down a larger deal from the Tigers to sign with the team he wanted to play with, the Boston Red Sox. A similar outcome with Bichette wouldn't be shocking.

Ranger Suarez doesn't sign until February

On one hand, Ranger Suarez checks all of the boxes. He's a 30-year-old left-hander who has a rock-solid 3.59 ERA in 104 starts in the last four regular seasons, and he has outstanding postseason numbers. His 2025 regular season was also his best. On the other hand, Suarez hasn't made 30 starts or thrown enough innings to qualify for an ERA title once in his big league career, and he's only losing velocity with his fastball.

A decrease of some level when it comes to fastball velocity makes sense, but Suarez's fastball velocity has dipped over 2 mph in the last three years. He's still getting results, but how many teams will be willing to give Suarez the massive deal he seeks, given his rapidly declining velocity, durability concerns, and the fact that if a team other than the Phillies were to sign him, they would have to give up a draft pick? Suarez's agent, Scott Boras, will hold out for the right deal, even if that means going into February to find it.

Orioles finally splurge on a starter, sign Framber Valdez

The Baltimore Orioles were willing to trade for Corbin Burnes in the 2023 offseason, but watched him sign with the Arizona Diamondbacks in the 2024 offseason. They didn't replace Burnes and their rotation was the biggest reason why 2025 went so poorly. Given their need for starting pitching, this is the year they'll finally splurge on a frontline arm. Framber Valdez makes a lot of sense for them.

Valdez might have some teammate concerns to take note of, but there isn't a free agent starter with a better track record. The ground ball specialist can keep the ball in the ballpark at a hitter-friendly Camden Yards and help lead an Orioles rotation in dire need of an ace back to the postseason.

Dodgers follow World Series win by winning Kyle Tucker sweepstakes

The Los Angeles Dodgers have repeated as World Series champions for a reason - they want it more than any other team. I wish this weren't the case, but the Dodgers are willing to spend to fill every possible hole on their team. Given how bad their outfield was in 2025, it'd honestly be surprising if they didn't seriously pursue Kyle Tucker in free agency.

Tucker is the best player available by a wide margin this offseason, and would add another MVP-caliber player to a lineup that already includes three MVP winners. This signing might feel unrealistic since the Dodgers are clearly good enough without him and MLB owners would freak out, but the Dodgers are as motivated as any team to win now. This fit makes too much sense.

MLB offseason trade/extension bold predictions

Tigers trade Tarik Skubal to Mets

Should the Detroit Tigers trade Tarik Skubal? Absolutely not. He should be extended right now. However, if they're unwilling to take extension talks with him seriously or if Skubal is uninterested, the last thing they should want to do is begin the season with him on their roster and no long-term deal in place. They'd risk losing him for nothing more than a draft pick as a free agent, which would hurt more than trading him.

If the Tigers do trade him, the New York Mets make too much sense. They're desperate for an ace, and there's nobody better than Skubal in that regard. David Stearns has shied away from spending big money on starting pitching, so why not trade prospects for someone without a long-term commitment instead? New York's farm system is as good as any, and features several players nearing the bigs. The Mets have the financial wherewithal and the pieces to get a deal done.

Cardinals trade Nolan Arenado to the Angels

The St. Louis Cardinals want to rebuild, and doing so involves trading Nolan Arenado, their veteran third baseman. Arenado says he's willing to accept trades to more teams this winter, making a trade far more likely than last offseason. In theory, the Los Angeles Angels do not make much sense for Arenado, a veteran who wants to win, but the Angels will trick themselves into thinking they're closer to competing than they are, and joining the Angels would allow Arenado, a California resident, to play close to home.

If contenders aren't interested in acquiring him, the Angels make more sense than anyone wants to admit. Even coming off a down year, Arenado is probably an upgrade over Yoan Moncada, so at least there's that.

Marlins hold onto Sandy Alcantara after uneven season

Sandy Alcantara has been in trade rumors ever since the 2025 season began, but he's still a member of the Miami Marlins, and there's a good chance that'll remain the case entering the 2026 campaign. A trade of Alcantara makes sense for a Miami Marlins team that isn't expected to compete in the short-term and has a good amount of starting pitching to build around even without him, but is now really the best time?

Alcantara had a 5.36 ERA in 31 starts in 2025. Sure, he finished stronger than he started, but it still feels like the Marlins would be selling low if they traded him now. Instead, why not wait and see how he performs at the start of the 2026 campaign, now that he's a full year removed from Tommy John Surgery? Alcantara is a Cy Young-caliber arm when healthy. Trading him for anything less than a star-level return right now would be a disservice, and it's hard to believe they'll have a star-level offer for him on the table, knowing the year he's coming off of.

Red Sox trade for Pablo Lopez, not Joe Ryan

Boston Red Sox fans who thought their team had traded for Joe Ryan at the trade deadline wound up being greatly disappointed, but trade talks with the Minnesota Twins should continue this offseason as the Red Sox search for their No. 2 starter and the Twins look to rebuild. Ryan should be Boston's No. 1 priority, but there's a chance the Twins will be more inclined to trade Pablo Lopez.

Lopez is the same age as Ryan, and both pitchers are under club control through 2027, but Lopez is making $21.75 million in both years, while Ryan will make significantly less in arbitration. The Twins would prioritize parting with the pitcher making more money, and the Red Sox, a big-market team, shouldn't mind taking on Lopez at what's still a team-friendly figure. He's far from a big name, but Loepz is absolutely a viable No. 2 starter Red Sox fans should be happy with if Boston is able to acquire him.

Pirates insult Paul Skenes with lowball extension offer

Paul Skenes is the Pittsburgh Pirates right now, and everybody knows that. He's so important to the present and future of this franchise to the point where even Bob Nutting will be willing to fork over a good amount of money in an extension to keep Skenes in the Steel City long-term.

With that being said, this is Bob Nutting we're talking about here. Any contract he's going to be willing to offer Skenes will be a hilarious low-ball that the right-hander will turn down at the spot. It's a shame, because this is a guy the Pirates should want to build their franchise around, but their owner will not take doing so seriously, frustrating Skenes in the process.

Brewers take less to avoid trading Freddy Peralta to Cubs

Fresh off the best regular season in franchise history, there's a good chance the Milwaukee Brewers will trade Freddy Peralta. Is this a slap in the face to the fans? Absolutely, but this is how the small-market Brewers operate. We've seen it with Corbin Burnes, Devin Williams and Josh Hader in recent years, so why expect anything different with Peralta, their ace?

As dumb as trading Peralta sounds on paper, the Brewers can get a ton back for the right-hander who is likely to leave after the 2026 campaign as a free agent anyway, and they've historically done well with these trades. One team in dire need of starting pitching that will be unwilling to spend big money for it is the Chicago Cubs, so they'd presumably be all over a Peralta trade. The fact that they play in the NL Central and are Milwaukee's biggest threats, though, makes it more likely that the Brewers would take a little less from another team to avoid gifting him to Craig Counsell and Co.

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