MLB offseason: Analysis for all major moves

The MLB offseason is underway. Follow along for analysis of all major transactions over the winter.

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Edward Cabrera I Kazuma Okamoto I Tatsuya Imai I December moves I November moves

Jan. 10

Cubs land marquee bat in Bregman

✍️ 5-year, $175M contract

What it means for Cubs: Chicago's awoken from its offseason slumber with an eventful three days. The addition of Bregman helps mitigate some of the offense lost with Kyle Tucker hitting free agency, and gives the Cubs an elite defense on the left side of the infield when paired with Dansby Swanson. Interestingly enough, Bregman was the second pick in the 2015 draft behind Swanson, and wears No. 2 because of it. Now the two are teammates.

Bregman brings a lot to a Cubs team that's coming off their first playoff appearance in five years. Chicago finished 27th in fWAR and 29th in OPS at third base last season, so Bregman immediately addresses a significant need. He also does a great job controlling the zone, and is coming off a season in which he posted a 14.1 K% and 10.3 BB%. That should mesh well with a Cubs team that struck out the sixth-fewest times in the majors in 2025.

Bregman's made the playoffs in each of the last nine seasons, has won two World Series titles, and has been heralded for his strong leadership. He'll be able to mentor some of the team's younger players in Pete Crow-Armstrong, Moisés Ballesteros, Kevin Alcántara, and Matt Shaw, though this does open the door for the team to potentially trade Shaw.

Wrigley Field will likely be the worst offensive home ballpark for Bregman in his career, but he surprisingly posted a higher OPS on the road (.875) than at Fenway Park (.761) last season, which is a bit of a surprise given his pull-heavy swing (47.4%). Bregman increased his hard-hit rate and exit velocity in 2025 over the previous season, though he sat somewhat troublingly in the 31st percentile in bat speed.

It's nice to see the Cubs being aggressive and acting like a big-market team once again. And, in Bregman, they have a core veteran locked up long term. Chicago only had $55 million committed in guaranteed salary in 2027, so it was able to stretch themselves in order to get Bregman signed.

What it means for Red Sox: So, what now for Boston? The Red Sox fully hitched their wagon to Bregman last season, and even with the opt-opts in his deal, it always felt like the two sides would work something out long term. But now, the organization caused an entire mess with Rafael Devers for one season of Bregman, and now they have neither. What makes it even worse is they are still in search of a middle-of-the-order bat, and are facing a potential hole at third base. Yikes.

Boston is the only team that has yet to sign a free agent to a guaranteed contract this winter. Yes, they've traded for Sonny Gray, Willson Contreras, and Johan Oviedo, but there is a clear reluctance to bid at the top of the free-agent market under Craig Breslow. This regime does not seem to want to spend big or offer long-term deals to players in their 30s.

With Bregman off the board, the pressure really ramps up for Boston. Luckily, there's still a number of options in free agency should the club feel any urgency. Signing Bo Bichette and deploying him at second base makes a lot of sense, though he will almost assuredly cost more than Bregman. Kyle Tucker fits on any team, though Boston is deep in left-handed hitting outfielders. Eugenio Suárez is the top third base option remaining on the market. There are also potential trade candidates like Alec Bohm, Brendan Donovan, Isaac Paredes, and Nolan Arenado.

Unlike other seasons, it doesn't appear as if the big free agents will see their markets collapse. So Breslow is likely going to need to step outside his comfort zone if he's to land a key bat in free agency, or swing yet another trade.

Jan. 7

Cubs finally make big move with Cabrera trade

What it means for Cubs: After making a number of depth moves, president of baseball operations Jed Hoyer finally took a big swing this offseason by acquiring Edward Cabrera. The right-hander is an enticing starter who's struggled to stay healthy throughout his five-year career. He threw a combined 294 MLB innings for the Marlins from 2021-2024 while landing on the injured list seven different times over that span with various ailments, including shoulder and elbow issues. What's encouraging for the Cubs, though, is that Cabrera is coming off the best season of his career: a 3.53 ERA, 3.83 FIP, 1.23 WHIP, and 150 strikeouts over 137 2/3 innings in 2025. He did miss almost four weeks in September with a right elbow sprain, but came off the IL to make two starts down the stretch, and will head into this spring healthy.

Chicago's done a great job getting the most out of its starting pitching in recent years, and there's reason to think they'll be able to do the same with Cabrera. He brings big-time velocity and also throws some strong secondary pitches, although hitters feasted on his sinker last year (.609 SLG). He was, however, able to lower his walk rate by over a full batter from 2024 and did a better job limiting home runs. Cabrera also comes with three years of team control at an extremely modest cost; he's projected to earn just $3.7 million through arbitration in 2026. Even if he's more of a No. 4 starter long term, the Cubs should still consider that a win.

With Shota Imanaga, Jameson Taillon, and potentially Matthrew Boyd all hitting free agency after the coming season, Chicago desperately needed to acquire a pitcher with some years of control. The question for the Cubs, though, is why they were willing to deal away their top prospect for pitching help, rather than just signing one of the top free-agent arms. Framber Valdez, Ranger Suárez, and Zac Gallen are all still available, and each has longer track records of health and success. They'll obviously all come at a much higher dollar figure, but Chicago sits well below the first luxury-tax threshold, and only has $55 million in guaranteed salary committed to the 2027 roster. This shouldn't be an issue for a big-market team.

If the Cubs are able to use the savings from Cabrera's salary to sign an impact bat or even another starter, this move makes a lot more sense. Owen Caissie wasn't going to take at-bats away from any regulars in 2026, but he was projected to potentially replace Kyle Tucker's production long term. Now, they might need to find that production outside the organization.

What it means for Marlins: Miami's once again dealt from its starting pitching depth to try and address a long-term offensive need. Trading Trevor Rogers to Baltimore for Kyle Stowers and Connor Norby at the 2024 deadline worked out well for the Marlins, and the team now hopes Caissie is another foundational offensive piece to build around. The 23-year-old brings a lot of left-handed power to his new club's lineup, and has a legitimate shot at making the Marlins' Opening Day roster. He put up a .937 OPS with 22 home runs in 99 games at Triple-A Iowa last season.

The biggest knock on Caissie is there's a lot of swing-and-miss in his bat. He struck out in 28% of his plate appearances at Triple-A in 2025, and in 41% of his 27 big-league PAs after being called up to the Cubs in August. Caissie's still very young and likely will benefit from having made his debut last year, but he'll need to do a much better job controlling the strike zone if he's to reach is potential.

Still, the Marlins have to be thrilled to get a player with Caissie's ceiling, along with two other prospects (Hernandez is now No. 12 in their system) for a pitcher that they seemingly couldn't trust to be reliably healthy moving forward. Cabrera's career season allowed Miami to sell high and deal from an area of strength in order to get a power bat with the type of potential they almost certainly would never pay for in free agency.

Jan. 3

Blue Jays keep spending with surprise Okamoto addition

✍️ 4-year, $60M contract

What it means for Blue Jays: Toronto's aggressive offseason continues. With so much focus on whether the club will sign Alex Bregman, Kyle Tucker, or Bo Bichette, general manager Ross Atkins went off the board by bringing in Japanese corner infielder Kazuma Okamoto. The 29-year-old enjoyed an incredible 11-year career in NPB and possesses the exact offensive profile that's made the Blue Jays successful.

Okamoto has posted six 30-plus homer seasons since 2018 and is coming off a year in which he slashed .322/.411/.581 with 15 home runs, 23 doubles, and only 36 strikeouts in 314 plate appearances (77 games). While his power numbers will likely dip when moving to MLB, his ability to make contact, hit the ball in the air, and not strike out is a skill set that should translate easily. The ceiling might not be as high as Munetaka Murakami's, but the profile offers a higher floor.

Okamoto's arrival spurs several questions for Toronto, most importantly: Where does he play? He's mainly split time at first and third base, with a little bit of work in the outfield in Japan. Although he grades as an OK defensive player at the hot corner, there are concerns that his glove might not be good enough at the position at the major-league level. With Vladimir Guerrero Jr. entrenched at first base for the next decade, the Blue Jays need to be confident that Okamoto can at least spend some time at third base. Toronto prides itself on bringing in players with defensive versatility, and as long as his bat plays, the organization will be able to find a spot for him. That said, the corner outfield and DH spots are now getting pretty crowded. The Blue Jays might need to move player(s) off the major-league roster to address other needs.

Bringing in Okamoto certainly doesn't take the Blue Jays out of the running for Bichette, Bregman, or Tucker, especially considering how aggressive the front office has been. However, this makes it slightly more complicated to get there. Toronto's CBT payroll now sits around $309 million for 2026 - the second-highest in MLB behind the Dodgers. The club hasn't really been operating with any payroll restrictions, but every team has its limits. Toronto has significant salaries coming off its books next winter, so maybe the front office sees this offseason as the perfect time to stretch its spending limits, given an underwhelming free-agent class and a potential lockout in 2027.

The Okamoto signing represents another really nice piece of business for the Blue Jays. If the team is able to still sign one of Bichette, Tucker, or Bregman, or acquire another star bat in a trade, the move looks even better. If Okamoto is the key bat the team acquires this winter, it changes the perception pretty drastically, as there will be more pressure on Addison Barger to build off a breakout season, and Anthony Santander to return to his 2024 All-Star form. We'll have to wait and see how the rest of the dominoes fall, but this is exactly the type of aggressive offseason you'd want to see from your team if it just fell short of winning a World Series.

Jan. 1

Astros address hole in rotation with Japanese ace

✍️ 3-year, $54M contract

What it means for Astros: Houston finally made a significant move with the surprise signing of Tatsuya Imai. The Astros needed to add at least one mid-rotation starter or better with Framber Valdez hitting free agency. Houston doesn't appear likely to bring back Valdez, though his return remains a possibility until he signs elsewhere. Imai can fill those innings, even if his ceiling is lower. If he pitches to expectations, he should slide in behind Hunter Brown and Cristian Javier as a capable arm.

Much like Munetaka Murakami, Imai signed a deal well beneath initial projections, as there's skepticism about how his stuff - in particular his secondary pitches - will translate to MLB and whether he can sustain his improved control. There's still a lot to be intrigued about after he pitched to a 1.92 ERA, 0.89 WHIP, and 9.8 K/9 over 24 starts last year in Japan. He only allowed six home runs across 163 2/3 innings. The ability to keep the ball in the park should boost his potential for success in the majors.

While Imai didn't land a lucrative, long-term contract, his ability to opt out after each of the next two seasons could be very valuable. If he pitches well in 2026, he can hit the open market again entering his age-29 season. This deal also carries almost no risk for the Astros. If Imai opts out, they get a very capable starter for at least one season at a relatively inexpensive salary ($18 million-$21 million based on innings pitched). Even if he struggles and performs like a back-end starter, he's only signed for three years at a reasonable cost.

Houston's front office did well to land Imai, but it really needs to add more impactful starting pitching. Brown is a legitimate ace, but there are a lot of questions behind him: Javier's made 15 starts over the last two seasons, Lance McCullers Jr. has continued to struggle to remain healthy and effective, and Mike Burrows has thrown more than 100 innings in a season just once since turning pro in 2021.

Earlier offseason moves 👉