The path to the World Series was right there for the Yankees.
In a weak American League and with one of the best starting rotations in baseball, the Yanks had a chance to make it back to the Fall Classic and vie for their first championship since 2009. But another team bested them in the postseason.
For the second straight season, an AL East rival defeated the Yankees in the ALDS. This time, the Rays swept the Yankees, leaving GM Brian Cashman,Aaron Boone and the rest of the organization searching for answers. What will it take to get this core group of players led by Aaron Judge over the hump? What pieces are needed to fill in the holes to mitigate mistakes and come out on top against teams that, on paper, the Yankees are better than?
There are no easy fixes in baseball, especially with a looming lockout and a new CBA, and -- at the time of this writing -- since Cashman and the powers that be have yet to speak to the media following the ALDS loss, it's unclear what the Yankees plan to do this offseason to rebuild a roster that was formidable on paper and expensive -- third-highest in baseball. A team that had the second-best record in the league, but just couldn't defeat a team whose salary ranked 26th in baseball.
Wins in the regular season are great, but it doesn't mean much if the results in the postseason aren't there. As Judge said after the ouster by the Rays: "We're the Yankees. I feel like [the front office] should go all-in and do what they need to do. If we've got holes, if it's finding certain players or personnel, whatever we need, you got to go out there and get it. That's why I signed back here to play with the Yankees is to fight for a championship every single year and go all-in."
Well, if we had the keys to the Yankees machine, here's a step-by-step process of what we'd do to fix the roster for 2027...
Rebuild bullpen by bringing back core
Every offseason, the bullpen needs rebuilding, and this one is no different.
David Bednar, Paul Blackburn, Ryan Yarbrough and Tim Hill are the notable names heading to free agency, and will be tough to replace. That's why our first order of business is to bring back the core.
Bednar was essential to the success the 2026 Yankees had. Cashman doesn't usually give out big contracts to closers, but a qualifying offer for one season would help if he accepts. If Bednar doesn't, then Cashman needs to buck the trend and lock down the right-hander to a multi-year deal to ensure the Yanks have the closer they can trust and know can handle the big city.
If a deal cannot be made, the New York needs to pursue other options like Raisel Iglesias.
Of the other free agent relievers, Blackburn would be my choice to bring back. Whatever the Yankees did to revive his career as a reliever, they can hopefully duplicate. A reunion is something that both sides should want, and a one or two-year deal (with an option) could bring back their setup man.
Yarbrough and Hill, while good, don't necessarily have roles in the bullpen anymore. Yarbrough was used only in long-relief situations when games were already out of hand, and Hill's effectiveness as a left-hander dipped this past season. After pitching to a 3.09 ERA in 2025, Hill's ERA ballooned to 4.60 in 2026. Brent Headrick is now the left-handed specialist, and the Yankees can use any one of their former starters (Clarke Schmidt, Luis Gil, Will Warren) in the Yarbrough role.
Those former starters can also fill the spots used by journeymen Michael Fulmer and John Schreiber, who are also free agents. Schreiber was actually pretty solid for the Yankees when they acquired him later in the season (1.64 ERA, 1.09 WHIP in 11 games), so bringing him back for cheap isn't a bad option, either.

Get a right-handed hitting catcher
The biggest need for the Bombers in 2026 was a catcher who can hit from the right side. They started the season with lefties Austin Wells and J.C. Escarra, but that hamstrung Boone's options off the bench and made the bottom of the lineup a black hole.
It wasn't much better once Ali Sanchez was called up to be that right-handed bat, as he slashed .244/.275/.302 with an OPS of .577 in 51 games.
There are a few intriguing upgrades in the free agent market, with Ryan Jeffers the top catching free agent available. While he would fit what the Yankees need, he could cost them too much, which they wouldn't want to do in a platoon or bench capacity. I believe the Yankees trust Wells not only in his defense and how he handles the pitching staff, but also that the offense he was once touted for is still in there.
Over his final 10 regular season games, Wells increased his batting average from .177 to .186 while smashing four home runs. That carried over into the postseason, where he had an OPS of .761.
Perhaps Tyler Stephenson, a former first-round pick, could fit the bill of a bench catcher. While his numbers don't match what Jeffers brings, the 30-year-old would be an upgrade over Sanchez and not cost what Jeffers would get on the market -- or a draft pick if the Twins extend the qualifying offer to him.
The end of the line for Stanton
Giancarlo Stanton has one more year on his contract before the Yankees have a chance to exercise a club option on the slugger.
Stanton is owed $25 million for 2027, but the Marlins are on the hook for $10 million, which means if the Yanks move on from Stanton, they'd only be taking on $15 million of dead money. The Yankees have done this before. Most recently, with DJ LeMahieu, DFA'ing the All-Star infielder and taking on his $22 million when they released him back in 2025.
Aaron Hicks had about $27 million left on his deal when the Yanks cut him in 2023.
It's time for the Yankees and Stanton to part ways.

The Yankees would likely be comfortable with Stanton on the roster if he could stay healthy and there wasn't a logjam in the DH spot.
Ben Rice, the Yankees' young All-Star, was relegated to the everyday DH spot after they acquired Luis Garcia Jr. at the trade deadline. And while Rice could play first base, his defense isn't up to par with Garcia's. And against a right-handed pitcher, you'd want both Rice and Garcia -- who has one more year of arbitration -- in the lineup.
Judge will also need some games at DH, further complicating the roster construction.
With a trade partner highly unlikely, the easiest solution is to cut Stanton and open up the spot for another bench hitter who can play the field. It's a tough decision involving a clubhouse leader, but it needs to be done.
Let the kids play
George Lombard Jr. and Spencer Jones were forced into big league roles in 2026 thanks to ineffective play and injuries. And the Yankees are probably better off for it.
Lombard feels like the everyday shortstop moving forward after Anthony Volpe was demoted and returned as a second baseman, and Jones more than held his own at the plate and defensively, filling in when Judge and Trent Grisham were injured.
Now that Grisham is almost certainly not returning, an outfield of Cody Bellinger, Jones, and Judge -- with Heliot Ramos as the fourth outfielder -- feels like the natural progression for the Yankees outfield.
And while not necessarily a kid, Volpe should get every chance to win the everyday second base job in the event Jazz Chisholm Jr. signs elsewhere. Volpe and Jose Caballero can be the versatile infielders the team needs. And they both can give Ryan McMahon a spell at third base. Heck, perhaps the Yankees can work with Garcia to be a second base option -- which he has 480 starts in his MLB career -- to give more lineup flexibility.
And then we have Carlos Lagrange. The flamethrower should be ready to make an impact in the rotation or bullpen.
Leaning on the kids to start the season would give the Yankees more athleticism, versatility, and keep costs down.
Use surplus of pitching to explore trades
The Yankees have plenty of arms and while it helped them navigate numerous injuries in 2026, they are better served dealing one or two young arms to bolster the roster.
When healthy, the rotation will be Cam Schlittler, Gerrit Cole, Max Fried, Carlos Rodon and Warren/Weathers.
Warren and Weathers are young, controllable arms who could be dealt to help rebuild the bullpen or even make a bigger splash. Could the Rockies' Hunter Goodman be pulled away from the team to give the Yankees the right-handed catcher they crave? Perhaps CJ Abrams could be the Chisholm replacement at second base.
Even if it's to replenish the farm system, being smart and creative from a position of strength should be one of the priorities this season.













