LAS VEGAS -- The sense of urgency across Major League Baseball right now is palpable. Everyone in the industry knows the game is shutting down when the clock strikes midnight on Dec. 2 and the owners lock the players out, and the transaction freeze that accompanies it makes the next three weeks that much more important.
In the final days before the last lockout in 2021, teams guaranteed more than $1.5 billion to free agents. This week at baseball's GM meetings, executives and agents are anticipating a similar deluge of deals as November progresses. The parties have skipped the standard early-winter formalities and gone straight to expressions of interest. And with the shortened timetable, offers are expected to follow soon -- especially following next week's owners' meetings.
The unknown labor situation's impact has been front and center on the minds of executives and agents here. Some believe owners see an opportunity to exert pressure on a large group of players and squeeze. Others think teams will spend like any other year to ensure players, in a potential legal battle, cannot suggest any sort of collusive behavior. It's not a bonanza free agent class by any means, but after an October in which three small-market organizations were among the four playing in league championship series, teams regard the current landscape as wide open enough that few plan to punt on the 2027 season.
With that in mind, here is the perfect offseason move for the dozen returning playoff teams and five others expected to be active during the shortened transaction window. While some of these teams will land multiple additions, the rule for this exercise was only one move per team and only one team per player.
Milwaukee Brewers
2026 results: 103-59, first place NL Central, World Series champions
The perfect transaction: The Brewers don't spend in free agency. Over the past half-decade, their two biggest deals were for Rhys Hoskins (two years, $34 million) and Jackie Bradley Jr. (two years, $24 million). And while the run to their first championship infused the organization with the sort of cash -- and cachet -- that would allow them to pursue top-end free agents, Milwaukee isn't suddenly going to deviate from a strategy that works. And, in this case, that's trading players they don't intend to sign to long-term deals a year before they reach free agency. The Brewers have no obvious weaknesses to fill, particularly with the strength of their farm system. And considering the paucity of high-end relievers in this market, the argument to add to their prospect cache is that much stronger. Trade closer Trevor Megill.
Tampa Bay Rays
2026 results: 98-64, first place AL East, lost in World Series
The perfect transaction: Exactly how much the Rays' payroll grows this winter under new owner Patrick Zalupski is one of the more interesting subplots of the offseason. Tampa Bay has already signaled that it intends to hold onto ace Drew Rasmussen, who will make $20 million in 2027 before he hits free agency.
While the Rays could use another bat, they'll have fast-moving catcher Caden Bodine in the big leagues next year, and center fielder Theo Gillen might not be far behind. The Rays' clearest susceptibility is its rotation, and with Shane McClanahan a trade candidate heading into his walk year, Tampa Bay could benefit from the return of a familiar face: the player everyone in the clubhouse pointed to as the Rays' unquestioned leader. Re-sign right-handed starter Nick Martinez.
Los Angeles Dodgers
2026 results: 100-62, first place NL West, lost in NLCS
The perfect transaction: Aside from Tarik Skubal, the Dodgers return all of the core players from a 100-win team. And even though Milwaukee slew them in a four-game NLCS sweep, the Dodgers are still a force, featuring a roster stacked with stars and a farm system ready to graduate young players to join what this year was the oldest roster in baseball.
Certainly the Dodgers will be in the mix on Skubal, but to what extent is unclear. Unlike Kyle Tucker last offseason, Skubal has no interest in a shorter-term, higher-dollar deal, which could disadvantage the Dodgers when contending with the New York Mets (or the San Diego Padres or Toronto Blue Jays). And considering their every-day lineup is set and their rotation is abounding with options, the Dodgers might replicate their 2022-23 offseason, which was limited to a handful of lower-dollar deals. If that's the case, the bullpen is a reasonable place for them to start. Re-sign left-handed reliever Alex Vesia.
San Diego Padres
2026 results: 91-71, second place NL West, lost in NLDS
The perfect transaction: The Padres are going to be busy. They have no rotation to speak of, so they are casting a wide net on starting pitching -- including Tarik Skubal. With their payroll in the $200 million range already, though, how much will new owner Jose Feliciano be willing to spend? Skubal will command at least $45 million a year. And while San Diego is not opposed to bargain hunting for arms, spreading out that cash among two or even three pitchers might better suit a rotation that returns only Randy Vasquez, with Joe Musgrove and Yu Darvish wild cards. The easy move -- the practical one -- is to lock up its ace for the past three seasons who just opted out of his deal with San Diego. Re-sign right-handed starter Michael King.
Cleveland Guardians
2026 results: 85-77, first place AL Central, lost in ALCS
The perfect transaction: While the Guardians' aggressiveness at the trade deadline helped them reach the ALCS, nobody expects them to replicate that in free agency. With the emergence of Chase DeLauter and trade for Jo Adell, their outfield is set for the first time in years. Their infield is solid, too, with the exception of first base, and between that and designated hitter, Cleveland should be in on midtier power bats.
What the Guardians really could use is one more solid starting pitcher, preferably on a shorter-term deal, with real upside. And the ideal candidate is right there for them. Sign right-handed starter Casey Mize.
New York Yankees
2026 results: 93-68, second place AL East, lost in ALDS
The perfect transaction: There are any number of perfect moves for the Yankees. Go get Teruaki Sato to solve third base? Sure. Bring back closer David Bednar? Absolutely. Sign Brandon Lowe to play second and abuse the short porch in right field? Yup.
The best of the bunch, though, would give them the sort of weapon manager Aaron Boone needs: a multi-inning reliever slinging some of the game's nastiest stuff. Spending on bullpen help is tricky, and the Yankees must do plenty more to address all their deficiencies, but landing a top-5 reliever in the game is a pretty good place to start. Sign left-handed reliever Adrian Morejon.
Atlanta Braves
2026 results: 94-68, first place NL East, lost in NLDS
The perfect transaction: The Braves need impact starting pitching. Bryce Elder and Grant Holmes are fine at the back end of a rotation, and Didier Fuentes will be an impact starter long term but could find himself innings-limited in 2027. But in a division primed to be loaded with good arms, Atlanta needs to keep up. That might mean right-hander Tyler Mahle, who served as a worthy complement to ace Chris Sale down the stretch. But this isn't about the moves the Braves are willing to make. It's about what would be ideal. And in this case, as good as Mahle was, there's another righty whose fastball sits in the low 90s and still finds ways to keep runs off the board. Sign right-handed starter Sonny Gray.
Chicago White Sox
2026 results: 84-78, second place AL Central, lost in ALDS
The perfect transaction: After trying to solve its starting pitching shortage at the deadline by adding Luis Castillo, Chicago is back for another go. And there is no shortage of available starting pitching. The White Sox won't be in on Skubal -- even though, with a payroll currently under $100 million, they absolutely should be -- but beyond him options abound. King, Gray, Martinez, Pivetta, Mahle -- not to mention Kaima Taira, Trevor Rogers, Clay Holmes, Kevin Gausman and Nick Pivetta. One pitcher in particular stands out, though, and he's among the hardest throwers in the class for a team that could use an infusion of fastball velocity. Sign right-handed starter Freddy Peralta.
Chicago Cubs
2026 results: 89-73, second place NL Central, lost in NL Wild Card
The perfect transaction: The Cubs need pitching, pitching and more pitching. Whether owner Tom Ricketts will provide the budget to fill those needs is the real question. Because as much sense as Skubal makes for the Cubs, the expectation is they won't be especially involved. And as much as they need a closer, Bednar and Morejon might find themselves outside of the Cubs' price range, too. (This is the part where we note the Cubs currently carry a $143 million payroll and have two outfield spots to fill as well.) If payroll constraints limit the Cubs to the best of the midtier starters, one brings the sort of high-octane stuff they are sorely lacking. Sign right-handed starter Kaima Taira.
Boston Red Sox
2026 results: 87-75, third place AL East, lost in AL Wild Card
The perfect transaction: Like the Cubs, the Red Sox are a large-market team whose ownership operates with midmarket sensibilities. They're not in on Skubal. They'll kick the tires on the best available bats in free agency. The perfect move for them -- a true impact bat -- would likelier be in the trade market. And there are options. CJ Abrams or Zach Neto would cost Franklin Arias, who could find himself at shortstop for Boston in 2027, so those are likely out of the question.
Arizona's Ketel Marte, on the other hand, would fit perfectly at second base. The concerns about his reliability are real. Boston talked about Corey Seager at the trade deadline this year, so that could be rekindled. If they do decide to spend money, though, there are worse options than getting a backup plan for Adley Rutschman (who hits free agency next winter) and adding another powerful right-handed bat who can play DH, too. Sign catcher Ryan Jeffers.
Philadelphia Phillies
2026 results: 88-74, second place NL East, lost in NL Wild Card
The perfect transaction: Just how much of an overhaul the Phillies undergo this winter remains to be seen, but they recognize that running back last year's outfit is a nightmare waiting to happen. The Phillies can go toe-to-toe with any team's best five players. Beyond that is the issue, and it has doomed them long enough that they need to prioritize multiple bats and fix a lineup with far too many holes. That starts in the outfield, and it just so happens that the three best free agent hitters this winter can all play outfield. Any of them would work, but one fits especially well. Sign outfielder Seiya Suzuki.
Pittsburgh Pirates
2026 results: 82-80, third place NL Central
The perfect transaction: Nobody anticipates the Pirates, in the current uncapped world, cosplaying the Dodgers. At the same time, they took a legitimate step forward on the field -- and that was with an off-year from Paul Skenes and Konnor Griffin missing half the season with injuries.
Pittsburgh shouldn't exactly run it back. The Pirates need to refurbish a bullpen that returns Mason Montgomery, Lake Bachar and too many question marks for comfort. Above all, though, they need to keep their offense humming. That's going to cost money. Particularly if they can keep at bay power-hungry AL East teams and bring back the best power hitter in the free agent class. Re-sign second baseman Brandon Lowe.
Houston Astros
2026 results: 81-81, first place AL West, lost in AL Wild Card
The perfect transaction: In truth, the perfect transaction is to blow up this team, trade everyone with real value and start from scratch under new general manager Randy Flores. Considering the sorry state of Houston's farm system, it could get very ugly very soon. Jeremy Pena is a free agent after 2027 and Yordan Alvarez following 2028. The only player under contract for 2029 is Jose Altuve, who will be 39 years old.
But if the Astros are planning on trying to win now -- and owner Jim Crane rarely deviates from that approach -- they need pitching. Beyond Hunter Brown and Peter Lambert, Houston's rotation is a long parade of maybes. So best to get someone coming off a career-best 169⅓ innings -- with room to grow. Sign left-handed starter Trevor Rogers.
Baltimore Orioles
2026 results: 79-82, fourth place AL East
The perfect transaction: The Orioles are telling people they're going to spend this winter -- just as they did last winter, when they gave $155 million to Pete Alonso. They have needs on the pitching and hitting sides, so if one were inclined to argue that arms are of the utmost significance, it would be tough to counter. But one look at the Orioles' outfield illustrates how badly things have gone in Baltimore. With failed prospects and the disaster of Tyler O'Neill's deal, the Orioles need a reset, and it can come in the form of the outfielder who performed best of all free agents at the position in 2026. Sign outfielder Randy Arozarena.
Toronto Blue Jays
2026 results: 79-83, last place AL East
The perfect transaction: The Blue Jays have become one of baseball's big spenders in recent seasons. Their projected cash payroll of $238.7 million, as calculated by Ethan Hullihen, ranks fifth currently, and they've indicated a willingness to further spend this winter. They'll be in the mix on Suzuki. They could use another starting pitcher. But keeping up with the Rays, Yankees and Red Sox necessitates upside plays, and there's only one free agent this winter with a 30/30 season on his résumé and the ability to play three premium positions -- one of which, second base, is a priority to fill. Sign infielder/outfielder Jazz Chisholm Jr.
Seattle Mariners
2026 results: 76-86, third place AL West
The perfect transaction: The most disappointing team in 2026 has a new manager, a load of talent and a wide-open division. Teams expect the Mariners to trade a starting pitcher -- George Kirby and Emerson Hancock are the likeliest to move -- and president of baseball operations Jerry Dipoto could dip into the free agent relief pool to strengthen a bullpen that regressed badly last year.
If there's a transformative move to be made, though, it's adding another bat to an offense that struggled last year and is losing its best hitter in Arozarena. And whether it's at third base or in a corner-outfield spot, the fit is exemplary. Sign infielder/outfielder Teruaki Sato.
New York Mets
2026 results: 74-88, last place NL East
The perfect transaction: Even if a salary cap is in place after the upcoming collective bargaining negotiations reach their conclusion, the New York Mets can sign Skubal and remain under the cap. They'd be top-heavy, sure, but with money to offload to teams that would need to reach a floor (Marcus Semien at $20 million) and an excellent group of players who still would not be in arbitration (Nolan McLean, Carson Benge, A.J. Ewing), it's perfectly reasonable. If there is no cap, there is no issue. And for both of those reasons -- plus a real need for quality starting pitching and the means to give Skubal a record contract -- the Mets find themselves in the strongest position to land the best free agent by a long shot this winter. Sign left-handed starter Tarik Skubal.

