No division spent more money on free-agent contracts this winter than the AL East, which, as a quintet, committed more than $900 million. That’s an impressive figure, considering Tampa Bay’s frugality and Boston’s bevy of trade acquisitions. It’s the rich getting richer, as this division has represented the American League in the World Series the past two years.
But which teams spent well, and which teams spent weirdly? And what exactly were the Rays up to, finagling their way into all those three-way deals? Let’s run through the richest division in baseball and grade their offseasons.
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Read more: NL East grades | NL Central grades | NL West grades
Toronto Blue Jays
Significant outgoing free agents: SS Bo Bichette, SP Chris Bassitt, SP Max Scherzer, RP Seranthony Domínguez, INF Isiah Kiner-Falefa, INF Ty France
Major moves:
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Signed SP Dylan Cease to a 7-year deal
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Signed SP Cody Ponce to a 3-year deal
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Signed RP Tyler Rogers to a 3-year deal
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Retained SP Shane Bieber on a 1-year player option
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Signed 3B Kazuma Okamoto to a 4-year deal
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Traded RP Matt Strahm to the Royals for RP Jonathan Bowlan
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Signed RP Zach Pop to a 1-year deal
Offseason grade: B
Toronto kicked off the winter with a bang, jumping the market to sign Cease on the largest deal for a pitcher in franchise history. They followed that by inking Ponce and Rogers to bolster their pitching depth. It was a show of force, a sign of intent, a celebratory continuation of Toronto’s historic October run. Their hot pursuit of Kyle Tucker, the market’s consensus top player, only served to reinforce the franchise’s rise to behemoth status.
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Ultimately, Tucker chose the Dodgers, leaving the Jays second-best once again. That development, alongside the departure of Bichette, makes this lineup definitively worse than the one that took the field for World Series Game 7. That’s not a slight toward Okamoto — he could well be an impact bat while providing Toronto the international stardom it’s been wanting for years — as much as a reminder of Bichette’s legacy up north.
The club’s complete disinterest in retaining the franchise icon, whose Game 7 homer was two outs away from immortality, was fascinating. Perhaps the singular focus on Tucker played a factor. Perhaps both parties were ready to move on. Either way, the Jays will enter 2026 with a worse lineup and an improved infield defense, with Okamoto at third, Ernie Clement at second and Andrés Giménez at short.
Had they landed Tucker, this would be an easy A, but Toronto failed to land a top-tier offensive partner for Vladimir Guerrero Jr.
Can the Yankees and Blue Jays repeat as the American League’s top two teams? Can the Red Sox and Orioles bounce back into the mix?
(Grant Thomas/Yahoo Sports)
New York Yankees
Significant outgoing free agents: RP Devin Williams, RP Luke Weaver, 1B Paul Goldschmidt, OF Austin Slater
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Major moves:
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Re-signed OF Cody Bellinger on a 5-year deal
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Retained OF Trent Grisham via qualifying offer
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Acquired SP Ryan Weathers from the Marlins for four prospects
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Re-signed INF Amed Rosario on a 1-year deal
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Re-signed 1B Paul Goldschmidt on a 1-year deal
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Re-signed RP Paul Blackburn on a 1-year deal
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Re-signed SP/RP Ryan Yarbrough on a 1-year deal
Offseason grade: B
The epitome of running it back, New York’s offseason was the transactional equivalent of reheating leftovers. That’s not an egregious strategy, considering how good the 2025 Yankees were, but the sheer scale of the continuity here is striking. In all, the Yankees retained six (!!) free agents from last year’s club and made just one significant external addition.
Keeping Bellinger in pinstripes was downright massive. He’s a perfect fit for the current roster, with his stellar outfield defense a real asset in Yankee Stadium’s spacious left field. Bellinger’s bat isn’t what it once was, but he finished second in WAR among Yankees last year, behind only Aaron Judge, for a reason. He’s a valuable player, one who helps give the 2026 Yankees one of the best lineups in baseball.
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Beyond that, it was a generally underwhelming winter in the Bronx. GM Brian Cashman is clearly comfortable banking on another strong year from his offense to go with a returning-from-injury Gerrit Cole and a full season of young flamethrower Cam Schlittler. But it’s hard to give a team with only one new face anything higher than a B. Besides, this bullpen still feels … under-addressed, with Williams and Weaver having left in free agency.
Boston Red Sox
Significant outgoing free agents: 3B Alex Bregman, SP Lucas Giolito, RP Steven Matz, RP Justin Wilson, OF Rob Refsnyder, SP Dustin May, RP Liam Hendriks
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Major moves:
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Signed SP Ranger Suárez to a 5-year deal
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Acquired SP Sonny Gray from the Cardinals for SP Richard Fitts and a pitching prospect
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Acquired 1B Willson Contreras from the Cardinals for SP Hunter Dobbins and two pitching prospects
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Acquired INF Caleb Durbin, INF Andruw Monasterio, INF Anthony Seigler and a 2026 Competitive Balance Round B pick from the Brewers for SP Kyle Harrison, INF David Hamilton and SP Shane Drohan
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Acquired SP Johan Oviedo, a pitching prospect and a catching prospect from the Pirates for OF Jhostynxon Garcia and a pitching prospect
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Traded RP Jordan Hicks and a pitching prospect to the White Sox for a pitching prospect and salary relief
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Signed INF Isiah Kiner-Falefa to a 1-year deal
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Nontendered 1B Nathaniel Lowe
Offseason grade: B
The rotation is better, the lineup is worse, and we are tired. Boston’s winter was exhausting to follow. I can only imagine how chief baseball officer Craig Breslow feels.
Opting to let Alex Bregman walk after spending all of 2025 lauding his leadership qualities and offensive reliability was a questionable choice. The immediate pivot to Ranger Suárez was odd but should push this rotation from good to excellent. The same is true for the additions of Sonny Gray and Johan Oviedo.
But the Red Sox didn’t exit October prematurely last season because they couldn’t prevent runs. No, they fell to the Yankees in the wild-card round because the offense lacked a difference-maker. Roman Anthony, who was hurt for the playoffs, might end up blossoming into that character, but that’s quite a lot to put on the shoulders of a 21-year-old. Willson Contreras is a proven commodity, but he’s closer to good than great. This corner outfield kitchen still has too many cooks between Anthony, Jarren Duran and Wilyer Abreu. Acquiring Caleb Durbin was a cheeky way to upgrade the infield, but he’s unlikely to compete for MVP votes.
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This winter also served to put a bow on last year’s Rafael Devers blockbuster, as two more pieces from that move, Jordan Hicks and Kyle Harrison, were traded away. Jose Bello, a 20-year-old with seven appearances in Low-A, is the only player left in Boston’s organization who was acquired in the Devers deal. It’s yet another reminder that the decision to trade the star was effectively a salary dump and little more. Some of the money saved will go into the pockets of Contreras, Gray, Suárez and others, but it’s difficult to look at this roster and not wonder how much better it would be with Devers in it.
Tampa Bay Rays
Significant outgoing free agents: SP Adrian Houser
Major moves:
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Signed OF Cedric Mullins to a 1-year deal
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Signed SP Nick Martinez to a 1-year deal
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Signed RP Steven Matz to a 2-year deal
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Signed OF Jake Fraley to a 1-year deal
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Acquired five prospects from the Orioles for SP Shane Baz
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Acquired UTL Gavin Lux in from the Cincinnati Reds as part of a three-team trade in which they sent Josh Lowe to the Angels
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Acquired 3B Ben Williamson from the Mariners as part of a three-team trade in which they sent a prospect and a draft pick to the Cardinals
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Acquired OF Jacob Melton and a pitching prospect from the Astros as part of a three-team trade in which they sent 2B Brandon Lowe, OF Jake Mangum and RP Mason Montgomery to the Pirates
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Acquired RP Steven Wilson from the White Sox for OF Everson Pereira and a prospect
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Offseason grade: B-
Tampa Bay’s carousel to nowhere continues. This franchise, renowned for both its penny-pinching ways and its ability to uncover hidden value, appears to be taking a small step back entering 2026. Thankfully, the Rays went about it in a fun way, inserting themselves into three different three-way deals.
Quite a bit of talent left town among Baz, Montgomery and both Lowes, with mostly prospects arriving in return. Mullins, Martinez and Matz are all worthwhile additions — a sign that even though the Rays are doubtful they’ll contend, the door is still open just in case.
In the main, this franchise is in something of a holding pattern until its stadium situation is resolved. That has been the case for some time now, though the new ownership group should help push the process forward. Until then, it’ll be more nibbling at the margins and hoping the farm system produces another star to pair with Junior Caminero.
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Baltimore Orioles
Significant outgoing free agents: SP Tomoyuki Sugano, C Gary Sánchez
Major moves:
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Signed 1B Pete Alonso to a 5-year deal
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Acquired SP Shane Baz from the Rays for four prospects and a Competitive Balance Round A draft pick
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Acquired OF Taylor Ward from the Angels for SP Grayson Rodriguez
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Signed RP Ryan Helsley to a 2-year deal
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Re-signed SP Zach Eflin on a 1-year deal
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Acquired INF/OF Blaze Alexander from the Diamondbacks for RP Kade Strowd and two prospects
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Signed OF Leody Taveras to a 1-year deal
Offseason grade: A-
After years of frugality, the Orioles finally broke out the checkbook for a top-tier free agent, inking Alonso to a paradigm-shifting, five-year deal. He’ll provide the type of dependable offensive production that Baltimore desperately lacked throughout its immensely disappointing 2025. More importantly, his signing was a signal of a new day in Charm City; new owner David Rubenstein is willing to spend at levels that the previous leadership group was not.
The two biggest trades of Baltimore’s winter were also significant departures in strategy for president of baseball operations Mike Elias, who has helmed the club since the 2018-19 offseason. Dealing away Rodriguez and his four years of control for an impending free agent in Ward was an uncharacteristically aggressive maneuver for the typically calculating Elias. The same is true of the Baz trade, in which Baltimore parted with a cornucopia of prospects to land a potential frontline arm.
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This was not a perfect offseason for the O’s — the bullpen could have used another boost, the rotation didn’t get a true ace — but it was a massive step forward. There’s an argument that no team in baseball improved as much as the one in Baltimore.
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