The New York Yankees' lineup should look very different by the start of the 2027 season.

Notably, two everyday players in the Yankees' batting order are hitting free agency: second baseman Jazz Chisholm Jr. and center fielder Trent Grisham. Both are expected to leave the Bronx over the winter. Chisholm could stay, but the writing is on the wall for Grisham after he severely regressed in 2026.

That being said, what appears to be a foregone conclusion for the Yankees actually creates multiple different routes for them to take. Grisham's departure will leave a vacancy in center field, thus creating yet another need to address, internally or externally.

How will the Yankees replace Trent Grisham?

The Yankees' outfield situation is in flux, with Cody Bellinger being the only sure bet to take one of the three spots. Aaron Judge's spot in right field is less certain because of his injury-riddled 2026 season, which may force the Bronx Bombers to deploy him more often as a designated hitter.

With Grisham expected to leave, the Yankees now face a decision regarding Spencer Jones. The 25-year-old showed improvement at the plate throughout his rookie season, and the best way for New York to continue his development is to play him every day. However, the question is whether he replaces Grisham in center field or Judge in right field.

Jones played 315.1 innings in center field in 2026, alongside 253.2 innings in right field. His center field metrics were rough. He totaled -4 Defensive Runs Saved and was worth -4 Outs Above Average.

Meanwhile, he looked a bit better in right field, recording zero Outs Above Average. Nonetheless, Jones has the speed and arm strength to become a plus defender at either position, which the Yankees are banking on, alongside further development as a hitter.

Alongside the Jones decision, the Yankees need to determine if Judge will primarily play right field or DH. Having Judge as the regular DH creates another question about Giancarlo Stanton's fit on the team. He's limited exclusively to that role, and if the Yankees removed Stanton as DH, it would effectively end his Bronx tenure.

If the Yankees want to stick with Jones in center and move Judge to DH, they would need a right fielder.

Heliot Ramos wouldn't be an adequate option, given his poor defense and platoon bat status. The best free-agent option would be Seiya Suzuki, who transformed into a Gold Glove finalist to complement an impact bat, but the Yankees might not want to offer him a long-term contract given his age.

If Jones moves to right, then the Yankees need a center fielder. In that case, the best option would be on the trade market, as the Cleveland Guardians could make Steven Kwan available. Kwan is in the final year of his contract and combines an excellent hit tool with great plate discipline and Gold Glove-caliber defense in center. However, he won't come cheap and is expected to be a rental for 2027.

All of these questions will need to be answered by the Yankees soon, because it's no secret that Grisham played his last game in pinstripes.

As strong as his 2025 season was, he failed to replicate that newfound offensive growth in 2026. Grisham also continued to decline in the field, which was exacerbated further by two separate hamstring injuries, putting him on the IL. Perhaps he can rebound in 2027, but Grisham simply isn't a good fit for the Yankees anymore, even if there's no clear answer to who replaces him at the moment.