Despite the inherent randomness of baseball, we are embarking on a championship series that includes three of the four top seeds in the league, with 2025 being a banner year for the franchises that earned a first-round bye. While most of the attention will be rightfully placed on the final four, it is also important to bid a proper farewell to the four teams that already packed their bags and are heading towards a tough offseason. Making the playoffs was an accomplishment for some of them, while for others it could mark the end of an era. In any case, we present a small post-mortem for the Yankees, Phillies, Cubs, and Tigers, with a look at how their offseason may play out.
Notable Free Agents: Cody Bellinger (player option), Paul Goldschmidt, Trent Grisham, Luke Weaver, Devin Williams
Out of all the early playoff exits, the Yankees’ may be the toughest one to assess. The magnitude of the franchise and its 16-year title drought will grab plenty of headlines, along with its upcoming exodus of notable names, suggesting that plenty of changes are afoot for the legendary franchise. At the same time, the Yankees were a tiebreaker away from earning the AL’s top seed, and they at least managed to eliminate their biggest rival in the postseason. Moreover, they should still have the right roster to produce a quick turnaround, with an underrated balance of stars and young players that ranks among the best in the sport.
The rational view suggests that most teams would be happy to be in this position, but New York’s expectations are almost irrational by birthright, and their fans will certainly clamor for major changes. The fact that the Yankees were outclassed by a division rival in the ALDS, with the team only showing signs of life in Game 3, only adds fuel to the fire, with the job status of manager Aaron Boone and GM Brian Cashman being fair game for speculation. All these factors are bound to create a perfect storm towards an interesting offseason.
Vladdy Jr. just did "DAAAAAA YANKEES LOSE!" 🤣 pic.twitter.com/VBwQEkmFm9
— FOX Sports: MLB (@MLBONFOX) October 9, 2025
Under George Steinbrenner, it is likely that a manager like Boone would have been run out of town a long time ago. With eight years at the helm, the former third baseman has consistently led teams through solid regular seasons only to flail in October. While the Yankees were resilient enough to overcome two elimination games against Boston, the Toronto series produced familiar results under Boone, including a lack of clutch hitting, lackluster defense, and a shaky bullpen. Aaron Judge may have posted his best playoff numbers in a decade, but it was still not enough to carry an offense that was constantly overmatched.
As the front office loaded at the deadline with plenty of relievers, letting go of Devin Williams and Luke Weaver is almost a given, but their free-agent hitters paint a different picture. Bellinger has already stated his intention to exercise the opt-out clause in his contract, while analyzing if Trent Grisham’s breakout power season is sustainable to warrant a mid-term contract is a major question mark. Paul Goldschmidt will probably retire and open a full-time spot for Ben Rice to man first base, while José Caballero will present a solid alternative in case Anthony Volpe’s issues are not fixable. The rotation will get a full year of Luis Gil and the emergence of Cam Schlittler, along with the likely return of Gerrit Cole, giving the Bombers a top-five rotation on paper.
With such a loaded roster, the Yankees could run it back and remain a contender, but the pressure of this quick exit will likely create a renewed sense of urgency. Judge remains a force, but his prime won’t last forever, and the offense could be complemented by a top-shelf free agent like Kyle Tucker, as he will probably become a priority for the front office. Ownership has also proven loyal time and again to Boone, and he is still under contract, so he will probably start the season in the dugout, albeit with a shorter leash going forward.
Notable Free Agents: Kyle Schwarber, J.T. Realmuto, Max Kepler, Ranger Suárez
Unlike the Yankees, who can still think of themselves as one the league’s best teams, the Phillies are about to enter a confusing age for their franchise. The consensus around baseball says that Philadelphia’s window title has been shut following another one-and-done playoff run, which again included home-field advantage following a strong season. The most recent exit continued the pattern of the Phillies disappointing their rabid home fans, with their 2022 pennant remaining their high point. Adding that the season ended on a truly traumatic play, it will surely be a long winter in the City of Brotherly Love.
An image Phillies fans will see all winter pic.twitter.com/OTmqCuCZ83
— Barstool Sports (@barstoolsports) October 10, 2025
As the only team that was bounced after a first-round bye, there are plenty of questions about the Phillies and how they blew their chance to finally get over the hump. Despite outscoring the Dodgers over their four-game series and posting better stats all around, the Phillies failed in several key moments, with manager Rob Thomson’s bullpen management coming under fire. Thomson’s job security will be at the forefront of many discussions around the team, especially after the front office surrounded him with plenty of weapons for the staff and lineup.
The untimely injury to staff ace Zack Wheeler played a part in this debacle, but the Phillies appeared equipped to overcome it with plenty of rotation standouts. It nearly happened, but a couple of Dodger rallies in games one and two were enough to turn the series, and now the front office has to decide what the next version of this team will look like. While Wheeler is expected back in full health, it is never a given for a veteran pitcher, and Ranger Suárez is certain to become one of the most coveted hurlers in the market.
A similar situation will come with Kyle Schwarber, as plenty of teams will salivate at the opportunity to add his prodigious power. Catcher J.T. Realmuto is not the force he used to be, but he should still be valuable for a couple of seasons, and he will have suitors. Even as the Phillies fancy themselves in the same tier of the Dodgers, Yankees, Mets, and other big-market teams, it is also true that they could benefit from a soft reset that reinvents the mindset of this aging roster. Christopher Sanchez has emerged as one of the best lefties in the sport, Bryce Harper continues to age well, and the team finally has a top-tier closer in Jhoan Duran, so there are enough pieces to build a title contender. In a division with the Mets and Atlanta looking for revenge, the Phillies need to be really smart in how they approach 2026.
Notable Free Agents: Shota Imanaga (mutual option), Andrew Kittredge (team option), Kyle Tucker
Following their first playoff series win in nearly a decade, the Chicago Cubs took the top-seeded Brewers to a winner-take-all Game 5, ending what became a memorable season around Wrigley Field. It is important to remember that the Cubs had spent their post-title era losing their famed homegrown core gradually, as fan interest dwindled and the front office failed to act like the big-market team they are. However, year two of the Craig Counsell era produced plenty of positive developments, and they should become the foundations towards a new era of Cubs baseball.
Words cannot begin to express the gratitude we have for all of you.
You are, and always will be, the best of us, Chicago. 💙 pic.twitter.com/c6ayORdNrw
— Chicago Cubs (@Cubs) October 13, 2025
While ownership and the front office committed to an aggressive trade for Kyle Tucker last offseason, their potential push him to re-sign him may be an indication of how the team views itself going forward. Tucker is almost sure to command a bidding war among the league’s free spenders, but the Cubs would seem to have the upper hand after a solid year in the North Side of Chicago. The nucleus of Pete Crow-Armstrong, Michael Busch, Nico Hoerner, and Dansby Swanson represents a lite version of the team’s title core, but they could reach another level if Tucker signs a long-term deal to stay around for the next decade or so.
The Cubs will also need to rebuild their bullpen, though that may be an easier task. While veterans like Andrew Kittredge, Drew Pomeranz, Brad Keller, and Caleb Thielbar combined to create a reliable relief corps around the playoffs, their track records suggest that they can be replaceable. The emergence of Cade Horton as a frontline pitcher, along with the likely return of Justin Steele give Chicago a high floor in the rotation, but retaining Shota Imanaga is almost a no-brainer, especially as he should not command a top-dollar contract to return.
In the end, the Cubs look ready to spend the rest of the decade battling with the Brewers atop the NL Central, as both teams look a clear step ahead of their counterparts. However, if Chicago wishes to contend for more than division titles, an aggressive hot stove season would be a great start.
Notable Free Agents: Jack Flaherty (player option), Gleyber Torres, Kyle Finnegan, Tommy Kahnle
It will be an offseason full of regrets in Detroit, even if the overall result can be considered a success. Losing a massive division lead deprived the Tigers of a possible first-round bye and an easier playoff path, ultimately leading to a heartbreaking loss in a 15-inning thriller in Seattle. This marked the second straight season with an exit in the ALDS for the Tigers, creating a tough situation in which the core will start to get expensive, but as part of a roster that still looks a few players away from reaching the league’s upper echelon.
The Detroit Tigers are 17th in payroll this year. They have $91M committed to 2026’s payroll and $28M committed to 2027’s payroll.
There is zero reason they do not pay Tarik Skubal. If they don’t, don’t villainize the team that gives him a record deal. Villainize the Detroit… pic.twitter.com/Mq5EB4qW1n
— BallPark Buzz (@BallParkBuzz) October 12, 2025
While the likes of Gleyber Torres and Jack Flaherty could be intriguing free agents, most of the chatter around the Tigers will happen around a 2027 free agent. Tarik Skubal is in line towards a second straight Cy Young award, and his playoff performances reminded everyone of his greatness. The Tigers may be several years removed from the time they had top-tier payrolls, but this roster could provide the motivation for ownership to break the bank and build around their most talented player. With a respected manager in AJ Hinch and playing in a soft division, there is a scenario in which the Tigers become the dominating team in the AL Central for several years to come.
On the flip side, if Skubal decides to test free agency after next season, he will likely be priced out of Detroit, and so this offseason will also require a number of contingency plans. The Tigers have finally seen many of their once-prized prospects develop into solid hitters, and they should continue to be the core for the foreseeable future. If the Javier Báez contract is no longer a complete bust, the front office could decide to invest even more money in the free agent market for solid complementary players, which could be enough to propel Detroit in 2026 regardless of what happens with Skubal in the long run.
