What's next for Yankees? After ugly playoffs sweep, Aaron Boone, Aaron Judge face the biggest questions

Another year of Aaron Judge's career has passed without a World Series title. The New York Yankees lost to the AL East rival Tampa Bay Rays at Yankee Stadium on Wednesday (TB 4, NY 3), and were swept in the best-of-five ALDS. Judge was stuck being a spectator during the playoffs after a lingering September calf injury kept him off the roster for the entire postseason.

New York's World Series title drought is up to 17 seasons, tied for the longest in franchise history (1979-95). Seventeen seasons is nothing for many teams. For the Yankees, it's an eternity. The World Series drought puts enough pressure on the organization. The fact that Judge, the franchise's greatest player since Derek Jeter, is entering his mid-30s only ups that pressure.

The Yankees, Los Angeles Dodgers, and Milwaukee Brewers are the only teams in baseball to win at least 93 games in each of the last three seasons. That counts for only so much, though. Turn on the YES Network or walk into Yankee Stadium, and the Yankees are quick to remind you they're the 27-time champs. This franchise is defined by titles and this is now 17 seasons without one.

Every offseason is important and this one is especially important for a Yankees team that has several core players getting up there in age (Judge, Gerrit Cole, etc.), and will have to square their top-three payroll ($336 million in 2026, per FanGraphs) with whatever changes the upcoming collective bargaining agreement brings to the game's economic landscape.

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Here now are three questions facing the Yankees following their latest postseason elimination.

1. Will Boone and Cashman be back?

The Yankees have reached the postseason in eight of Aaron Boone's nine seasons as manager and, in those eight postseasons, they went 7-0 in series against teams with a worse regular-season record and 1-8 against teams with the same or a better regular-season record. That one series win was over Cleveland in the 2020 Wild Card Series, during the pandemic season. Boone's Yankees have bullied lesser teams and been unable to beat equal or better competition.

This is not solely a Boone problem -- the manager can't swing the bat or throw the ball for his players -- but it does reflect poorly on him, especially because it spans multiple generations of players across those nine years. The same goes for New York's unending defensive lapses and inattentiveness. The players change, yet the sloppiness remains. Again, it reflects poorly on the manager.

Boone has managed 1,355 regular-season games, seventh most in Yankees history and by far the most among managers who have not won the World Series. (Buck Showalter is second with 582.) Again, it's not all on Boone. The manager can only do so much. But at some point, this becomes your legacy. You're the manager who can't get his team over the hump and win a ring.

Nine years is a very long time for a manager. It's a very long time for a manager who has led his team to a World Series title (Joe Maddon got five years with the Chicago Cubs, for example), something Boone cannot claim to have done. The marks against him are mounting. The sloppiness persists, the inability to beat better teams in the postseason continues, etc.

There are three things working in Boone's favor, however. One: Boone has another year remaining on his contract. Two: GM Brian Cashman and owner Hal Steinbrenner are in his corner, or at least were coming in 2026. Maybe that has changed over the last seven months, but those are the two people you want in your corner in this organization. 

And three: This is a bad offseason to bring in a new manager. The seemingly inevitable lockout and truncated spring training mean there won't be much time this winter for a new manager to come in and build relationships with his players (team personnel, including managers, cannot have contact with players during the lockout). Those relationships are already in place with Boone.

As for Cashman, he just completed his 29th (!) season as general manager, and he has never built a losing team. His contract is up this offseason, so if the Yankees are going to make a change atop the baseball operations hierarchy, this would be the time to do it. That change could even come with Cashman being elevated to a president role, leaving someone else to handle the day-to-day.

I would bet the farm on Cashman returning next season. He is basically an honorary Steinbrenner. Hal Steinbrenner trusts him and the two are very close. Cashman is successful based on whatever metric Steinbrenner uses to define success (it isn't World Series championships, obviously), which is why he's remained the GM so long. I doubt those feelings have changed.

Boone's status is more up in the air. After back-to-back ALDS losses to an AL East rival, the Yankees could scapegoat someone, and the manager is often that scapegoat. And again, the persistent defensive lapses and inability to beat equal or better teams in the postseason reflect poorly on Boone, even if those are organizational failings more than managerial failings.

The easiest move would be to bring Boone back, let him play out the last season of his contract as a lame duck in 2027, then make a managerial decision during a non-lockout offseason. It does feel like things have gone stale, though, that the Boone era has run its course. If nothing else, a managerial change would not be difficult to justify.

2. Will Judge's role change in 2027?

Judge, the Yankees captain, will of course be written in pen into the middle of the lineup next season and moving forward. The bigger question is his role on the defensive side of the ball. Judge will turn 35 in April, and, like most players his age, he has slowed down in the field. He was once an above-average right fielder. Now he's closer to average, and maybe worse than that.

There is also a self-preservation component to this that I'd argue is more important than defensive value. No. 99 missed 99 games this year due to a fractured rib that he suffered diving for a ball in April. Two years ago, Judge ran through the Dodger Stadium wall and missed two months with a toe injury. He had a shoulder injury in 2017 that was made worse by a collision with the wall.

A soon-to-be 35-year-old player, especially one as large as Judge, moving from right field to DH is the natural order of things, and it's getting to be time for Judge to make that transition. I'm not sure I would call them obstacles, but there are a few things the Yankees must consider and work through ahead of such a transition:

1. Giancarlo Stanton: Stanton, 37 in November, is signed through 2027, though the Yankees owe him only $15 million (the Miami Marlins are paying the rest), which is a relative pittance given their payroll. The 2017 NL MVP did not play in the regular season after April 24 due to three separate calf injuries, though he was on the postseason roster as a pinch-hitter. 

The Yankees have eaten much more than $15 million to release post-prime players within the last decade (Jacoby Ellsbury, Aaron Hicks, DJ LeMahieu, Alex Rodriguez, etc.). They could do that with Stanton to clear DH for Judge, but Stanton is revered in the clubhouse. He is a team leader who was not on the postseason roster out of pity. He's still a power threat. He's just hurt a lot.

Also, Stanton's frequent injuries mean the DH spot may (likely will) open for Judge at some point next season that way. If the Yankees have insurance on Stanton's contract, that's another reason to keep him. They'll be reimbursed for some portion of his salary if he misses enough time. If Stanton is healthy, the DH spot likely won't be available for Judge.

2. Ben Rice: With Judge limited to 66 games, Rice was New York's best hitter this year. He slugged 41 homers during the regular season, more than the next two Yankees combined, and he was their best hitter in the postseason. Rice is, however, another DH. He started 95 games at DH, including 45 of the last 49 games (and all five postseason games), and only 53 games at first base.

The Yankees could simply move Rice to first base full-time to clear the DH spot for Judge, though Rice is a poor defender, plus they acquired first baseman and 30-homer man Luis García Jr. at the trade deadline. García is under control next season and is a superior defender to Rice. The best possible lineup includes García, Judge, and Rice (and Stanton). How do you make the pieces fit?

García and Stanton will be free agents after 2027. The easiest move would be to play Judge in right field one more season, then transition him to full-time DH in 2028 and move Rice to first. And if the DH spot opens via injury next year, the Yankees can give Judge at-bats there. Soon, though, the Yankees will have to move their captain out of the field to keep him on the field.

3. How can they upgrade their offense?

Two things are true. One: The Yankees badly missed Judge during his absence. Every team would miss their best player when he spends four months on the injured list, and, in this case, Judge has been the game's best hitter over the last half-decade. The Yankees missed him more than most teams would miss their best player because Judge is better than every other team's best player.

And two: New York's offense lagged significantly this year and you can't simply blame it on Judge getting hurt. He's one player. A great player, but still only one player, and one player can only take one out of every nine at-bats in a given game. Judge's absence does not explain the Yankees receiving little from catcher, shortstop, third base, and center field this season.

For all intents and purposes, Judge's season ended on May 31. He did play seven games between the rib fracture and calf strain in September, but was rusty after the long layoff (4 for 23) and essentially a non-factor. Here are New York's numbers on offense:

Plate appearances

2,222

3,775

Runs per game

5.17 (4th in MLB)

4.25 (23rd in MLB)

Homers per game

1.46 (1st)

1.34 (5th)

Batting average

.243 (13th)

.230 (29th)

On-base percentage

.334 (5th)

.297 (30th)

Slugging percentage

.436 (2nd)

.394 (23rd)

Those numbers cover thousands of plate appearances. This sport just doesn't work in such a way that one injury, even to a player as good as Judge, can cause a team's on-base percentage to slip 37 (!) points in-season or cause a team to score nearly one fewer run per game. Judge's absence contributed to the offensive decline, no doubt, but he alone doesn't explain it.

Jazz Chisholm Jr. and Trent Grisham, both of whom underwhelmed in 2026 after career-best seasons in 2025, are free agents and unlikely to return, creating openings at second base and in center field. The Yankees could fill those positions internally with Anthony Volpe and Spencer Jones, respectively, but they have an entire offseason to look for better, and they should.

Third base must be addressed. Ryan McMahon hit .213/.279/.357 despite being heavily platooned and given favorable matchups, and his once-Gold Glove-caliber defense has slipped now that he's into his 30s. The Yankees owe him $16 million next season, but that can't stand in the way of a move. Going from McMahon to even an average third baseman would be a big upgrade.

Second base, third base, and center field are three positions the Yankees should address this offseason. The free agent class is not strong at all -- Chisholm very well might be the best available position player -- which could push the Yankees to the trade market. In that case, they could deal from their rotation. Here is their rotation depth chart going into 2027:

1. RHP Cam Schlittler
2. LHP Max Fried
3. RHP Gerrit Cole
4. LHP Carlos Rodón
5. LHP Ryan Weathers
6. RHP Will Warren
7. RHP Clarke Schmidt (returning from UCL surgery and biceps neuritis)
8. RHP Elmer Rodríguez

Warren threw 156 innings with a 3.92 ERA and matching under-the-hood numbers (3.94 FIP and 4.34 expected ERA) this season. When that guy is your sixth-best starter, you're in a great place. Warren is under team control through 2030, and while he won't headline a blockbuster trade on his own, he has real trade value and would have plenty of suitors if dangled.

Trading rotation depth is always risky (Cole, Fried, Rodón, and Weathers all missed time with arm injuries in 2026), but the Yankees could do something like, say, trade Warren for a bat, then sign a free agent to backfill innings. I'm not sure any team wants to throw money at this group of free-agent position players. Signing a pitcher, then trading arms for bats is the more sensible move.

The Yankees also must figure out the back of the bullpen with closer David Bednar and top setup man Paul Blackburn hitting free agency, but they're pretty good at cobbling together relief corps on the cheap. The offense is a much more pressing issue. Judge will be back next year and will hopefully stay healthy. It's the supporting cast around him must be improved.