Jazz Chisholm Jr.’s free agency could send the Padres down a road they know all too well.
If there’s a familiar pattern in A.J. Preller’s offseason approach, it’s the willingness to chase a player who might not be a perfect fit on paper but still looks too tempting to pass up. That possibility is back in play with Chisholm Jr., who is coming off an uneven season with the Yankees and now enters the market with his future in the Bronx far from settled.
Chisholm Jr. saw several offensive numbers dip in 2026, turning what should have been a pivotal walk year into a disappointing one by his standards. Even so, he still managed 41 stolen bases and 69 runs scored, a reminder that the talent remains real even if the production backed up in spots. As a free agent, he would like to return to the Yankees, but the team and its fans may see things differently if his asking price climbs too high.
That’s where San Diego enters the picture.
The Padres do not exactly have an obvious opening for Chisholm Jr., who can play second base and third base. Jake Cronenworth and Manny Machado are already in place, which makes this more of a luxury pursuit than a roster necessity. But Preller has never been shy about adding a player first and figuring out the rest later, especially if the upside looks appealing enough.
For Padres fans, that kind of move would bring back some old memories.
The parallel here is hard to miss: Chisholm Jr. could become the latest big-name infielder to land a massive deal, much like Xander Bogaerts did four seasons ago when San Diego gave him 11 years and $280 million. That contract is still far from finished, and the Padres are already looking for ways to move it. Bogaerts’ legs have slowed, and his bat has lost some consistency along the way.
Chisholm Jr. would almost certainly come with a similar kind of financial commitment. He has two All-Star selections, the versatility to move around the infield and enough speed to rank among the quicker players at his position.
The early years of that kind of contract would likely look strong. The concern is what comes later, when a player reaches age 33 and the decline phase starts to take hold.
This past season already offered a glimpse of the volatility. Chisholm Jr. showed he can slide offensively, even if the rest of his game still gives teams something to like. The question is whether that risk would bother Preller enough to keep him away.
San Diego needs a major bat this winter, and that much is clear. Whether Preller goes all the way in on Chisholm Jr. is the bigger question. Another aggressive swing could be coming.
In Other News...
Padres Fans Just Got An Offseason Glimpse Of Rising Arm Bradgley Rodriguez
Bradgley Rodriguezs offseason started the way a lot of young pitchers in San Diego do, with a little bit of buzz and a lot of attention. The Padres right-hander, who debuted in 2025, has quickly become one of the more interesting arms on the roster, and after the clubs playoff exit at the hands of the Brewers, he gave fans a fresh look at how he spent the early part of the winter.
The update had nothing to do with mechanics or a throwing program. Rodriguez unveiled a full arm sleeve tattoo, a personal touch that stood out almost as much as his work on the mound this year. After a strong regular season and a steady postseason contribution, it was a reminder that even in the aftermath of elimination, one of San Diegos rising pitchers is already moving into the next chapter. [Read more 🡒]
Padres Offseason Push Starts With One Roster Problem They Can't Ignore
The Padres are heading into the winter with plenty to sort through after a strong late-season push ended with a National League Division Series loss to the Milwaukee Brewers. The bigger issue now is less about what went wrong in October and more about how much of the core that got them there can actually be preserved, especially with important rotation pieces nearing free agency or tied to decisions that could reshape the staff.
San Diego also has to think beyond the starting five, because the roster needs help in the outfield and the bullpen has its own looming questions. Keeping the relief group intact would go a long way toward maintaining one of the clubs biggest strengths, but that kind of continuity is rarely simple in an offseason like this, when the Padres are trying to protect both depth and upside at the same time. [Read more 🡒]
Padres Enter Crucial First Offseason Under Owners Facing Immediate Pressure
Jos E. Feliciano and Kwanza Jones are now officially in charge of the Padres after MLBs unanimous approval of their $3.9 billion purchase, ending the Seidler familys ownership run and putting the franchise into a new era with immediate expectations attached. The new group has already pledged to keep investing in the club and maintaining the organizations community focus, a reassuring message for a fan base that has grown used to ambition at the top.
The timing, though, makes this a far more demanding handoff than a standard changeover. San Diego has just come out of the 2026 postseason and now heads into an offseason loaded with roster uncertainty, from looming free-agent decisions to the question of how Joe Musgrove fits as he comes back from injury. For owners who arrive with pressure already baked in, the first winter is rarely about patience, and this one could set the tone for everything that follows. [Read more 🡒]