Yankees Weigh Options for Left-Handed Batters

If Aaron Judge can switch it up and hit from the left side, he could solidify his status as the standout left-handed hitter the Yankees need to diversify their batting lineup.

While Brian Cashman has not ruled anything out, it doesn’t mean he’s actively pursuing left-handed bats at the moment.

One name on the radar is Jazz Chisholm Jr., who just wrapped up a remarkable season with 31 home runs and as many stolen bases. He’s having a productive year on base and has shown interest in a long-term stay in the Bronx, though talks about a contract extension seem unlikely. Expect other teams to be inquiring about him come winter.

Cashman was quite positive during last week’s winter meetings, noting, “I think he’s part of the solution right now.” He highlighted Chisholm’s athleticism and contributions since joining the team two days before the deadline. Cashman praised him as an All-Star second baseman with impressive skills ranging from offense to defense. Yet, the final outcome for the team still depends on various factors, including the performance of others, like Ryan McMahon at second base or Ben Rice behind the plate. They all add depth, particularly from the left side.

“We’re keeping an open mind,” Cashman added. “But remember, each of these players has their own individual strengths.”

The primary focus for the Yankees continues to be re-signing Cody Bellinger, who did exceptionally well against left-handed pitching last season.

As this unfolds, Cashman acknowledged existing gaps in left field and the bullpen. He’s also exploring ways to enhance the rotation and is contemplating some “challenge trades” to navigate through a roster that has become overly left-handed.

Should a team make an enticing offer for Chisholm in any of these areas, it could lead to a trade. However, losing him could create a significant gap at second base since he boasted a 4.4 fWAR, ranking fourth among his peers in 2025.

Cashman noted they are open to trading skilled players but acknowledged that it wouldn’t be easy due to their strong roster. Chisholm is projected to earn about $10 million in his final arbitration year, and despite mixed performances during his 18 months with the Yankees, he has mostly delivered. There was indeed a tough moment when he made an awkward play during a poor series in Miami, and he showed frustration when left out of the lineup against a challenging pitcher in the Wild Card Series. Still, his positive contributions have outweighed the negatives.

Manager Aaron Boone has consistently praised how the team has managed Chisholm since bringing him over from the Marlins at the 2024 trade deadline.

Some teams might look to snag a player likely entering his fourth arbitration season, especially if they’re not anticipating a contract extension. However, the Yankees are not poised to be in that situation.

Regarding potential contract extensions, the Yankees’ last significant offers were to Aaron Hicks and Luis Severino, both of which didn’t work out as hoped.

Cashman is undeterred by these past examples when considering new extensions. Efforts were made with both Judge and Juan Soto, but they didn’t pan out. Yet, Hal Steinbrenner has voiced a general hesitance towards extensions.

“I think it’s going to be more complicated because it could exceed the average annual value,” Cashman stated. “We’ve already got significant commitments to manage, so any new deals will complicate our flexibility moving forward.”