Biggest questions facing MLB's eliminated division series teams
The playoff field has once again halved as four more teams fell in the LDS and now turn their attention to the offseason. Here are the biggest questions facing the New York Yankees, Chicago Cubs, Detroit Tigers, and Philadelphia Phillies this winter.
In the Bronx, the attitude has always been championship or bust. Well, it's now been 16 years - the second-longest championship drought in the franchise's storied history - since the Yankees paraded down Broadway. This isn't to say they're about to rebuild, but their latest loss leaves them at a major crossroads heading into 2026.
The major players will all be back next season. Aaron Judge remains New York's centerpiece and isn't the problem here. Offensively, he'll continue to form a fearsome tandem with Giancarlo Stanton (health permitting), and Ben Rice should take over first base full time going forward. Starting pitching will also continue to be a strength for the club, led by Max Fried, Carlos Rodón, a more experienced Cam Schlittler, and a returning Gerrit Cole.
Everything else is a question mark. Considering the manner in which the Yankees crashed out of the playoffs, it's time for the organization to take a long, hard look in the mirror and ask some serious questions. The basic miscues in the field, the lack of awareness, the inability or unwillingness to work counts and be patient at the plate - none of that can happen again. In order to return to the mountaintop, the Yankees need to reimagine themselves.
Since this is the Yankees we're talking about, they'll be linked to almost every major free agent. Poaching Bo Bichette from the team that just eliminated them would be a great start to their offseason. Yes, Bichette has some defensive issues at shortstop, but his hitting style is exactly what the lineup needs. New York has enough power hitters who strike out a ton; it needs a Bichette to consistently put the ball in play at the top of the order, no matter where he's playing defensively.
Re-signing Cody Bellinger needs to be a priority for general manager Brian Cashman as well. The former NL MVP may never return to those heights, but he's a perfect fit for this team and should age well at Yankee Stadium. New York also has to finally decide whether former top prospect Spencer Jones, whom it's hung onto through the last several trade deadlines, is finally ready for the show. If not, it's time to trade him. Ditto for Jasson Domínguez, who was the Yankees' primary left fielder in 2025 but got just one plate appearance during the postseason.
Then there's the bullpen, where David Bednar in the ninth inning is now the only sure thing. Luke Weaver, a 2024 playoff hero, has probably pitched his last game in pinstripes after falling back to earth this postseason. Devin Williams' rocky year leaves his return in question, although he could probably be had at a reasonable price. Most importantly, New York's 'pen needs stability and consistency alongside Bednar. Expect the team to chase the likes of Taylor Rogers, Raisel Iglesias, or even Edwin Díaz if he opts out.
The Yankees will be good again in 2026. Judge will likely lead them back to the playoffs, and they could win the division. But is that all they want? What they do this winter will tell us everything we need to know.
Orion Kerkering's unfortunate season-ending error may have closed the door on the Phillies' championship window. It's clear that executives Dave Dombrowski and Preston Mattingly have their work cut out for them. Still, all is not necessarily lost here.
With an aging and expensive core, Philadelphia has no choice but to continue going all-in on winning. The first step is obviously to re-sign Kyle Schwarber. From there, everything else can fall into place. Retaining J.T. Realmuto at a reasonable cost would be helpful given the hole he'd leave behind the plate, and Harrison Bader could be brought back to solidify left field.
The pitching side is where things get a bit dicey. Owner John Middleton has never been shy about spending money, but will he do it to retain Ranger Suárez? You can never have enough starters, and Suárez is excellent at his job. Keeping him would also provide insurance if Zack Wheeler's recovery doesn't go as planned. But Suárez is 30 and spent time on the injured list with back issues each of the last two seasons. Signing him to a long-term deal presents another high-risk, high-reward proposition for a team with plenty of those deals already on the books.
The Phillies need to decide how big of a role their younger players will have in 2026. Top prospect Andrew Painter racked up strikeouts in Triple-A this season, albeit with an ERA above five. Is he ready for a rotation spot? Aidan Miller and Justin Crawford are on the verge of reaching the majors as well, and both could become major contributors either next year or in '27. Miller's path is more complicated, though, as he's blocked at shortstop by Trea Turner.
The bullpen will also look different. Jhoan Duran and Matt Strahm will be back. Expect Dombrowski to chase veteran arms to help deepen the team's relief corps. It's worth asking whether it's better for Kerkering, a reliable reliever for much of the last three years, to get a fresh start elsewhere after his memorable error.
Overall, there will be necessary change coming to Citizens Bank Park, but the Phillies can still contend. They just have to be more careful about balancing the present with the future.
The high-priced, big-market Cubs were bested for NL Central supremacy and then booted from the playoffs by their bitter rivals from a much smaller market. Now, they face a winter of uncertainty, and much of it is their own doing.
The most important question revolves around Kyle Tucker, the team's marquee addition last December. Tucker will command a large contract as one of the two biggest free-agent position players available this offseason despite having a rocky first (and perhaps only) season on the North Side of Chicago. Most of Tucker's All-Star production came in the first half; after the break, he slumped to .231/.360/.378 with just five homers and missed the majority of September with a calf injury. He returned for the playoffs and hit well during the club's NLDS loss, albeit as a strict DH.
The Cubs have the money to pay Tucker what he wants, so ownership can make a long-term union happen if that's what it desires. It could also wait Tucker out and hope he'll settle for a short-term bounce-back deal with player options if the down year suppresses his market. That avenue would allow the Cubs to either keep Seiya Suzuki as a full-time DH or trade the Japanese star for pitching, thereby opening a full-time spot for top prospect Owen Caissie.
And that brings us to the pitching staff, which is clearly their most pressing offseason need. Including those with club options, there are 10 pending free-agent pitchers on the Cubs' roster, meaning plenty of turnover is coming.
Left-hander Shota Imanaga represents the biggest pitching conundrum. The 32-year-old holds a $15-million player option for 2026. If he exercises it, which is likely, the Cubs then have to decide whether to pick up a two-year, $42-million club option to keep him through 2028. Imanaga was an All-Star in his first MLB season but struggled in the second half and was hit so hard by Milwaukee in the NLDS that Chicago passed him over for a bullpen day in the decisive Game 5. Still, he's been an important veteran starter on a team that's desperate for pitching.
Even if Imanaga sticks around, pitching remains a top priority. Strikeouts were a major issue for the Cubs, whose staff posted the fourth-lowest K/9 in the majors as a unit. Those issues continued into the playoffs, where their K/9 sits last among all postseason teams. They had only three healthy starters in October and relied heavily on their bullpen to push the NLDS to Game 5. The absence of potential NL Rookie of the Year Cade Horton, not to mention Justin Steele, was really felt during the division series, and it's part of why Chicago lost.
While the team should be in on any and all relievers, acquiring top-tier starting pitching - particularly starters who can rack up strikeouts - by any means necessary should be the No. 1 offseason priority. Horton looks like a future ace. Steele should return in the first half of next season. And the trio of Imanaga, Matthew Boyd, and Jameson Taillon is fine at the back end of the rotation (assuming none are traded). But the Cubs need help. Dylan Cease's strikeout power would be perfect for this rotation, and they should be all over him in free agency. Zac Gallen is another solid free-agent option. A need-for-need trade sending Suzuki to a pitching-rich team in exchange for a top-tier starter would also help, if he's willing to waive his no-trade clause.
All of this, of course, assumes the Cubs act like the big-market flagship franchise they are. Wrigley Field is a cash cow, and the Ricketts family has shown a willingness to spend in the past. Ideally, the loss to Milwaukee will be a wake-up call, and Chicago will flex its financial muscle to regain control of the NL Central. There should be no more excuses.
A Tigers season that started with such promise ended in the division series for a second straight year. Their latest exit was much more painful, though, and work needs to be done after the team blew a 15.5-game lead to lose a very winnable division.
Let's start on the mound, where the top of Detroit's rotation will look just as it did in 2025. Tarik Skubal and Casey Mize are still in town (we'll get back to them in a minute), while Jack Flaherty is a lock to opt in for 2026 after leading the AL in losses during his up-and-down campaign. Reese Olson, who missed most of the second half with a shoulder injury, should be healthy next spring. It would be shocking if Alex Cobb, who didn't throw a pitch after signing a $15-million deal last offseason, or Chris Paddack returned.
With Jackson Jobe unlikely to be back until late 2026 at the earliest, Detroit is left with one open rotation spot. The question is whether the team fills the void internally - Keider Montero and Sawyer Gipson-Long could compete for the job in spring - or spends money on a veteran starter. The Tigers' system isn't loaded with top-tier pitching prospects, so it wouldn't be a bad time for owner Chris Ilitch to show he's serious about fielding a winner and open his wallet for a Dylan Cease, Ranger Suárez, or Framber Valdez. Any of those frontline starters would form a fearsome duo with Skubal and improve Detroit's chances of advancing in October.
Speaking of Skubal and money ... it's almost time for the Tigers to pay up. The reigning AL Cy Young winner is entering his final year of arbitration, and his contract status will hang over the franchise well into next season if a deal isn't done. Securing their ace long term should be the absolute top priority for Ilitch and president of baseball operations Scott Harris. Skubal won't come cheap as a Scott Boras client, but he's worth every penny. Locking him up soon would send a message to other free agents that the Tigers are serious about spending and winning. They simply can't afford to let Skubal reach free agency.
Offensively, they have to decide what to do about Gleyber Torres. The All-Star had a solid first season in Detroit and should command a nice sum as the likely top available second baseman this winter. For as good as he was, though, letting Torres walk is something they can justify, and his money could be better spent elsewhere. The Tigers have a glut of infield prospects - led by No. 2 overall prospect Kevin McGonigle - who are knocking on the door, making it easier to part ways with Torres. On the other hand, they could choose to either retain Torres or chase a Bo Bichette and then use McGonigle as trade bait.
Under the late Mike Ilitch, the Tigers consistently spent big to build sustainable winners filled with superstars. It's time for his son Chris to do the same, both to help this iteration of the team reach the next level and to convince Skubal to stay long term. The front office and ownership should approach this offseason with a sense of urgency because, in many ways, time is running short. If they aren't prepared to do that, then it's time to shop Skubal and Mize, who's also a pending free agent, and sink back into a rebuild. It would be an absolute shame if that happened.