Jazz Chisholm’s next move could become one of the more interesting free-agency decisions of the winter, and the San Diego Padres have already been floated as a possible landing spot.
The Yankees second baseman is heading into an offseason where his future is up in the air, especially after he was left out of the starting lineup for some playoff games. Chisholm has said he wants to stay in New York, but his situation could still push him toward other options once free agency opens.
“Chisholm, an All-Star for the second time in 2025, endured a down year at the plate and struggled both offensively and defensively in four appearances in the playoffs. Manager Aaron Boone left Chisholm out of the Yankees' starting lineup for two postseason games, including their season-ending loss on Wednesday.
The fans at Yankee Stadium booed Chisholm after he fouled out to first base as a pinch hitter in the bottom of the seventh inning. Nevertheless, Chisholm would rather continue his career with the Yankees than exit in free agency," MLB Trade Rumors' wrote.
If he does leave New York, Bleacher Report’s Zachary D. Rymer sees San Diego as a strong fit.
“Starting pitching will need to be a priority, but another bat should also be a must. The Padres specifically need more left-handed thump after getting just a .385 SLG from that side of the plate.
They could also use more offensive production at second base, where Jake Cronenworth struggled in 2026. Also, does anyone else get the sense that San Diego would be a good spot for Chisholm's energy?
He plays with a chip on his shoulder, and that's been the Padres' whole vibe as they have fought the Los Angeles Dodgers for control of the NL West throughout the 2020,” Rymer wrote.
A pairing with Fernando Tatis Jr. would make for a compelling look in San Diego, and Chisholm’s high-energy style would seem to match what the Padres bring to the field. He would also arrive with the added appeal of having won a Silver Slugger not too long ago.
For a club that could use more production from the left side and at second base, Chisholm checks a few boxes if he becomes available.
In Other News...
Yankees Outfield Plan Is Starting To Take Shape After Grisham
The Yankees outfield picture is already starting to come into focus with Trent Grisham trending toward an exit after a disappointing season. Grisham did provide some pop with 18 home runs, but the overall package never quite clicked, and his poor defensive metrics only add to the sense that a reunion in the Bronx is unlikely once he reaches free agency.
Jacob Young could be one of the names to watch as the Yankees sort through their next move in center field. The Washington Nationals regular brings the kind of glove the club values, even if his offense has been modest, and the possibility of a platoon role suggests the Yankees may be looking for a different kind of solution than the one they got from Grisham. [Read more 🡒]
Yankees Fans Just Got The Answer They Feared From Hal Steinbrenner
A day after another postseason exit, Hal Steinbrenner spent an hour on Zoom with Brian Cashman talking through what went wrong for the Yankees, and the message out of that conversation was hardly a surprise to anyone who has followed this franchise closely. Steinbrenner pointed to the injuries that hit key players as part of the explanation for the early finish, while also casting doubt on the idea that harsh outside criticism would somehow be the thing that changes the clubs outlook.
Aaron Boone also addressed the situation separately, and the manager kept the focus on his own ability to guide the team moving forward even after New York again fell short of advancing. For Yankees fans, the bigger question now is not just what was said in these internal talks, but whether the organization is prepared to treat another disappointing October as a push for change or simply as another reminder of what went wrong. [Read more 🡒]
Hal Steinbrenner Just Sent Yankees Fans A Clear Aaron Judge Message
Brian Cashmans latest contract extension gave the Yankees a chance to reset the conversation around the front office, but Hal Steinbrenner used the moment to make clear where he stands with Aaron Judge and the broader clubhouse culture. In a joint press conference, Steinbrenner addressed Judges public call for the team to go all in, and framed his response around the standards he wants upheld inside the organization.
Steinbrenner said he spoke privately with Judge, while also backing the clubs approach to the captains injury situation during the postseason. The message was less about a public back-and-forth than a reminder that, in Steinbrenners view, the Yankees expect players to work hard and follow the rules the team has in place, even as the pressure to build a true championship roster keeps growing. [Read more 🡒]
