October never even started for the Chicago Cubs, Boston Red Sox and Houston Astros.
With a trio of wild-card sweeps Wednesday, they became the first teams to make exits in the 2026 MLB playoffs -- on the last day of September.
So, what’s next for Chicago, Boston and Houston -- and all of the other teams 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 wild-card series
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
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
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
