2026 MLB playoffs: Offseason questions for eliminated teams

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Aaron Judge: Yankees front office should go 'all-in' (0:39)

A few days ago, it seemed as if the Chicago White Sox had all but punched their ticket to the American League Championship Series.

And then ... the Sox lost three games in four days, squandering their 2-0 AL Division Series lead over the Cleveland Guardians and becoming the last team from the LDS round to bow out of the 2026 MLB playoffs.

So what's next in Chicago -- and in all of the other towns that won't be celebrating a World Series parade this fall? For every eliminated contender this October, ESPN MLB experts Jorge Castillo, Bradford Doolittle, Alden Gonzalez, Jesse Rogers and David Schoenfield list its key free agents and biggest offseason questions and also make their predictions for the long, cold winter ahead.

Teams eliminated in division series

Chicago White Sox

Eliminated by: Cleveland Guardians

Key free agents: LHP Sean Newcomb, OF Randal Grichuk

Biggest offseason priority: The White Sox established a nice foundation with their position players in 2026, especially in the infield, where Miguel Vargas (3B), Colson Montgomery (SS) and Munetaka Murakami (1B) each hit 30-plus home runs. And with top prospects Caleb Bonemer and No. 1 pick Roch Cholowsky on his way -- plus breakout seasons from Chase Meidroth and Sam Antonacci -- the team is more than set in that area. Where it needs work is in its starting rotation.

Sean Burke and Davis Martin led the way to the playoffs this year, but neither is a true ace. Additionally, the White Sox had the fewest innings from starting pitchers of any playoff team. They might need a little bit of a more traditional path on the mound if they want to return to October next year. Openers and multi-inning stints from relief pitchers can take you only so far -- as evidenced by the team's exit this postseason. The team can work Hagen Smith and Noah Schultz into the rotation, while Burke and Martin aren't going anywhere unless one is traded. Figuring out their five-man rotation will be the priority this winter.

What will happen with Luis Castillo in 2027? Owed $21 million for next season, Castillo was a summer trade who did not work out this year. Will the team give him another opportunity in the rotation come spring training or is he destined for the bullpen? Chicago isn't likely to let him go before next year, but if things don't turn around for the veteran once the season starts, he'll be a DFA candidate.

Offseason prediction: The White Sox engage Murakami in discussions for a longer-term deal after his current one expires after 2027. It might not be the massive payday he was in line for when he shot out of the gate this year, but it still should end up being the largest contract earned in White Sox history. That's if both sides can come to an agreement. Whenever a player is within a year of free agency, there's always a chance he tests the market -- but in this case, there seems to be a genuine desire to complete a deal. -- Rogers


New York Yankees

Eliminated by: Tampa Bay Rays

Key free agents: RHP David Bednar, 2B Jazz Chisholm Jr., CF Trent Grisham, RHP Paul Blackburn, 1B Paul Goldschmidt

Biggest offseason priority: Restocking the relief corps. Bednar was a rock at the back end of the bullpen in 2026, tallying 35 saves with a 2.47 ERA in his age-30 season. He was nails after a rocky start, with a 1.30 ERA in his final 43 appearances. He's the top free-agent closer, and he's going to get paid. Blackburn won't be in Bednar's pay grade, but the former starter should have his list of suitors after shining out of the bullpen with a 1.69 ERA in 62 appearances. Blackburn, who was claimed off waivers from the Mets last season, joined a growing group of former starters the Yankees have taken from the scrap heap to convert into elite relievers.

They are two of the seven New York relievers going into free agency. The Yankees could re-sign any combination of the six -- Tim Hill, Ryan Yarbrough, Michael Fulmer and John Schreiber are the others -- but they'll likely turn to internal (and more affordable) options to fill out the group. That list includes prospect Carlos Lagrange and former AL Rookie of the Year winner Luis Gil, who was moved to the bullpen this season. If the Yankees don't trade from their rotation depth, they also could move one of Clarke Schmidt, Will Warren and Ryan Weathers to the bullpen.

Who replaces Chisholm and Grisham? Chisholm and Grisham were important contributors, but the Yankees have replacements ready. And both players will likely land multiyear contracts elsewhere -- assuming Chisholm declines the Yankees' qualifying offer, should they extend it. Anthony Volpe or Jose Caballero could replace Chisholm as the every-day second baseman. Spencer Jones could slide into Grisham's spot in center field. Or the Yankees make a splash for bigger upgrades at those spots.

Offseason prediction: A year after closer Devin Williams and setup man Luke Weaver left the Bronx for the Mets, the Yankees re-sign Bednar and Blackburn to stabilize the back end of their bullpen. A bonus prediction: They add a right-handed-hitting catcher to pair with Austin Wells via free agency or trade. Ryan Jeffers is the top free agent option. -- Castillo


Atlanta Braves

Eliminated by: Los Angeles Dodgers

Key free agents: RHP Tyler Mahle, RHP Raisel Iglesias, LHP Martin Perez, UT Mauricio Dubon, DH Dominic Smith

Biggest offseason priority: Shortstop. Ha-Seong Kim is also a free agent and he was a $20 million disaster, hitting .116 in 147 at-bats. Dubon ended up starting the most games there, 51, but he's also a free agent, and his best role is as a utility guy. Rookie Jim Jarvis started 35 games, but he hit .207 with one home run. Prospect Tate Southisene is a couple of years away.

Aside from that, re-signing Mahle, who pitched so well after coming over at the trade deadline, is another big priority given the uncertainty of Spencer Strider and Spencer Schwellenbach returning from injuries. Didier Fuentes will be ready to replace Iglesias as closer, so given the subtraction of Kim, Fuentes and other free agents, there should be room to bring back Mahle.

Is it time to consider extensions for Ronald Acuna Jr. and Ozzie Albies? Remember those super team-friendly contracts signed years ago? They're getting close to the end. Acuna has two team options left, while Albies is entering the final year of his deal. The Braves will pick up the 2027 options -- $17 million for Acuna and $7 million for Albies -- but you wonder about the long-term futures in Atlanta for both players. Acuna didn't have a superstar season and got injured once again, playing 102 games. Albies played all 162 games but hit just .237/.293/.392. The easiest and perhaps wisest thing to do is just to let those contracts play out. Given his injury history, Acuna is going to be a risky bet in his 30s. Albies is entering his age-30 season, but that declining OBP is a problem. The Braves got unbelievable value out of those deals. No need to overpay now.

Offseason prediction: The shortstop free agent class is weak. (J.P. Crawford doesn't have much range and the others all played for the Braves -- Dubon, Kim and Jorge Mateo.) There could be a trade for somebody like Milwaukee's Joey Ortiz, who might be squeezed out of a crowded infield situation there, or taking on a potential salary dump like Boston's Trevor Story. (The Red Sox would have to eat most of his $25 million salary, plus he has declining range metrics as well.) So ... maybe bring back Dubon? Otherwise, the payroll situation dictates moving on from Iglesias, but Fuentes has the talent to be an elite closer. Mahle will be in demand, and maybe the likes of JR Ritchie and AJ Smith-Shawverr, plus Strider and Schwellenbach, will have the Braves feeling good enough about their rotation options. -- Schoenfield


San Diego Padres

Eliminated by: Milwaukee Brewers

Key free agents: RHP Michael King (player option), LHP Adrian Morejon, RHP Walker Buehler, 1B Ty France, LHP Robbie Ray, RHP Casey Mize

Biggest offseason priority: Nick Pivetta spent enough time on the injured list for his player option to turn into a club option, allowing the Padres to retain him for 2027. It's a boost for a team that will see a lot of starting pitchers depart via free agency this offseason, but more is needed. Assuming Pivetta is back, he'll be joining a rotation headlined by Yu Darvish and Joe Musgrove, two guys whose health will be a complete unknown going into next season. Outside of them, the Padres have Randy Vasquez and JP Sears as depth -- and little else.

How much will the new owners spend? Jose E. Feliciano and Kwanza Jones have said all the right things thus far, talking up their desire to win, complimenting late owner Peter Seidler's vision and speaking passionately about the Padres' importance to the community. We'll find out soon just how committed they are from a financial standpoint. The Padres have a lot of big contracts on their books -- for Manny Machado, Xander Bogaerts, Jackson Merrill and Fernando Tatis Jr. -- but also lots of holes that their depleted farm system can't fill. In order to continue to contend, they need to continue to spend. To what extent Feliciano and Jones do so remains to be seen. And before we learn that, we'll need to see what baseball's economic model looks like under a new collective bargaining agreement.

Offseason prediction: In the midst of a champagne celebration after clinching a third consecutive trip to the playoffs, Tatis stood by Morejon and clamored for general manager A.J. Preller to bring him back. "Pay him!" Tatis continually yelled toward Preller in Spanish. The guess here: The Padres find a way to bring Morejon back, pairing him with Mason Miller in the back end of their bullpen to continue to shut down games. Another guess: They also bring back France, who signed a minor league deal and performed like one of the game's best first basemen in 2026. The Padres need them both. -- Gonzalez

Teams eliminated in wild-card series

Boston Red Sox

Eliminated by: New York Yankees

Key free agents: RHP Sonny Gray ($30 million mutual option), LHP Patrick Sandoval, IF Isiah Kiner-Falefa

Biggest offseason priority: Gray had a terrific season but has hinted at retirement, telling The Boston Globe that he would retire "in a heartbeat" if his family wants him home, so replacing him in the rotation could be the priority. A healthy Garrett Crochet will help fill that void, but after trading away so many starting pitchers and pitching prospects over the past year (including Kyle Harrison, Shane Drohan, Hunter Dobbins, Connelly Early, Anthony Eyanson and Kyson Witherspoon), adding depth in that department looks necessary.

Will they trade Jarren Duran? While the Red Sox had a revolving door at shortstop and second base in 2026 -- six different players started at short and seven at second -- those positions will probably be resolved in 2027 with top prospect Franklin Arias and Curtis Mead, the trade deadline acquisition the Red Sox were going to play at second base until he got injured his first game with the team. Trevor Story still has one more year left on his contract, but there's no reason he should be playing ahead of Arias next season.

That leaves trading Duran on the agenda. Roman Anthony's nearly four-month stint on the IL meant the four-outfielders-for-three-positions problem never actually turned into a problem, but after hitting just .207/.266/.361, Duran is clearly fourth on the depth chart. His trade value took a nosedive, but he still somehow has two years left of team control, and the Red Sox will find a team willing to take a chance on him.

Offseason prediction: Even if there was no looming lockout, it would project as a quiet offseason for the Red Sox. The trades for Willson Contreras last offseason and then Mead, Adley Rutschman and reliever Erik Miller at the deadline brought in players with control through at least 2027. Maybe Duran gets traded, maybe it's time to give up on Tristan Casas ever getting healthy. If Gray returns -- $30 million is certainly a reason to stick around -- the Red Sox are in outstanding shape to return to the playoffs and make a run at the AL East title. -- Schoenfield


Chicago Cubs

Eliminated by: San Diego Padres

Key free agents: RHP Kevin Gausman, OF Ian Happ, OF Seiya Suzuki, LHP Shota Imanaga, LHP Matthew Boyd (mutual option), RHP Clay Holmes (player option), C Carson Kelly (mutual option)

Biggest offseason priority: The Cubs need to rebuild their pitching staff and that includes both their rotation and bullpen. The good news is they can concentrate on that part of their team because they have enough position players to fill the void left by Happ and Suzuki, who are both likely to leave the team via free agency. But what does that staff look like with Justin Steele and eventually Cade Horton returning from injury? Do Holmes and Boyd return? One but not the other? And what does one make of a bullpen that was inconsistent? It's a yearly debate under Jed Hoyer, who doesn't like to spend big money on closers. The Cubs have paid for that decision at times -- though in other moments they've developed some good relievers. Pitching is the key to their offseason, whether it comes from within or from outside the organization.

What will they do at catcher? Kelly has been nothing short of excellent over his two years in Chicago. He's great at calling a game. He's great at the ABS challenge system. And he has been more than a serviceable hitter. Plus, he's a leader and a glue guy in the clubhouse. Chicago has an up-and-coming catcher in Owen Ayers and still has Miguel Amaya under team control, and Kelly has a mutual option, so it'll be interesting how the team handles the position.

Offseason prediction: The Cubs probably will do what they usually do: spend some on their rotation, but not on the pen. They shelled out a few dollars for middle relievers in Phil Maton and Hunter Harvey last year and it didn't work out, so unless they have an appetite for a big-time closer -- they almost never do -- it feels as if they'll try to build their bullpen with minor additions and under-the-radar guys. Boyd might return, but Holmes, Imanaga and Gausman will test the market, opening up some slots in the rotation. -- Rogers


Houston Astros

Eliminated by: Chicago White Sox

Key free agents: RHP Bryan Abreu, 3B Isaac Paredes (club option, converted to mutual option if Paredes lands in top 10 of AL MVP balloting)

Biggest offseason priority: The Astros navigated the stretch run without a general manager after Dana Brown was let go in late August. That was after the draft and the trade deadline, so the committee guiding the front office was able to make it work. Going forward, the Astros will need to find or promote a new lead executive, then empower him to implement his own processes. Given the influence of owner Jim Crane and ex-player Jeff Bagwell, a vocal analytics skeptic in the past, the outcome of the search will tell us a lot about how the higher-ups in Houston see the landscape of best practices in the industry. That can be good, or not, but either way it's time the Astros returned some continuity to their most important baseball operations position.

How much weight should the Astros put on this playoff appearance? Of course the Astros deserved to celebrate the latest in the spree of division titles the franchise has won over the past decade. And it's certainly true that Houston's ability to climb out of a 20-31 hole in late May was fairly remarkable. Nevertheless, the Astros had to win their last two games to reach .500 at season's end and were outscored by 32 runs overall. If not for the low bar the AL West set this season, the Astros would have been watching from the playoff sideline for a second straight season. Thus, as the next Astros GM sets out, they'll have to be clear-eyed about it. The starting point for the club is one of mediocrity and there aren't enough upward-pointing trajectory arrows on the roster. Maybe a full reset isn't needed, but at the very least, the short and the long terms will have to be given equal shrift, or else this thing could really crumble in a hurry.

Offseason prediction: Houston has had a coterie of bright front office personalities working out of the spotlight going back to the Jeff Luhnow days. The most obvious course of action would be to promote one of them -- someone like assistant GMs Charles Cook, Gavin Dickey or Connor Huff. But just as crucial is to empower that hire to build and run their own front office. Questions about whether the Crane/Bagwell-led leadership team is willing to fully commit to that are why a promotion from within seems like the most likely course of action. The first indication about how this will go probably will be whether the Astros wait to have a new baseball chief in place before committing to bringing back manager Joe Espada in 2027. -- Doolittle


Philadelphia Phillies

Eliminated by: Atlanta Braves

Key free agents: 3B/1B Alec Bohm, 2B Luis Arraez, IF Edmundo Sosa, LHP Jose Alvarado, LHP Tim Mayza

Biggest offseason priority: Probably right field. But after yet another bullpen meltdown in the playoffs, Dave Dombrowski will once again look to reconfigure the relief corps. Don Mattingly made the right call in going to Jhoan Duran in the seventh inning of the Game 1 loss to the Braves, but the issue is the lack of depth that necessitated going to him so early.

The Adolis Garcia signing was a flop, so the Phillies eventually traded for Arraez and reconfigured their defense on the fly, shifting Bryson Stott to third base, Bohm to first base and Bryce Harper to right field. Harper presumably moves back to first base and Stott to second. Bohm is a goner, with top infield prospect Aidan Miller hopefully ready to take over third after missing almost all of 2026 because of a back injury. With the overall decline of the offense, that leaves a power-hitting right fielder -- good luck! -- as the biggest need.

Do the Phillies run it back with this same group ... again? There are worse places to start than a rotation with Cristopher Sanchez, Zack Wheeler and Jesus Luzardo, so there's no need to blow this up after another disappointing playoff exit. The position player core was not good in 2026, and Harper and Kyle Schwarber, the two mainstays who carried this group, aren't getting any younger, so this is an ever-growing concern. Check out the WAR of some of the other returning players: Trea Turner (-0.1), Justin Crawford (-0.2), All-Star Brandon Marsh (0.4), J.T. Realmuto (0.0). Bohm was below replacement as well. There isn't much immediate help on the farm either, other than Miller and pitcher Gage Wood.

Offseason prediction: No team in recent history has stuck with the same core group of players as long as the Phillies have. They will finally see some turnover with Bohm's departure, but there isn't a lot of room to maneuver here. This will be the team once again, with Dombrowski probably solving right field in the same way as 2026 -- signing a low-upside veteran -- and trying to improve the bullpen that had the worst ERA in the majors in September and was 21st for the season. -- Schoenfield