Yankees Could Face A Real Jazz Chisholm Problem This Winter

Will the San Diego Padres land Yankees All-Star Jazz Chisholm Jr. to bolster their roster and make a World Series run?

The San Diego Padres are heading into an offseason that sounds as ambitious as it is urgent, and one of the names already tied to them is a familiar star from the other side of the country.

AJ Preller made it clear this week that the Padres are not looking to stand still. Speaking on a conference call with reporters, the team’s president of baseball operations said the goal is bigger than just getting back to the postseason.

“I think we all understand that we have a few more steps we need to take, and the ultimate goal is to be playing at this time of year and be playing on the big stage in a World Series situation,” Preller said. “So everybody here at Petco [Park] - the commitment from ownership, from everybody, is going to be about how do we take another step or two and continue to get better."

He also laid out the broad areas San Diego could attack.

“I think there’s a lot of ways to get to that step," he added. "I think we’ll examine it all: improve the bullpen, improve the rotation, improve the offense.

But I think we’re in position to take advantage of that. We’ve got to probably take another step or two here to get where [we want] to get to.”

That offensive piece matters. The Padres have watched their lineup go quiet in the postseason for three straight years, and that leaves the front office with more than one hole to patch.

The starting rotation needs work, too. But if San Diego is going to add impact bats, one name to watch is Yankees free agent Jazz Chisholm Jr.

Bleacher Report’s Zachary D. Rymer ranked the Padres as the No. 3 landing spot for Chisholm in free agency, and the fit is easy to see on paper.

Back in 2025, Chisholm looked like he was lining himself up for a monster payday. The outfielder-turned-second-baseman put together a season with 31 home runs, 80 RBIs, 31 stolen bases and an .813 OPS. He made the All-Star team, won a Silver Slugger award and played elite defense.

His walk year, though, did not stay on that same track. Chisholm closed the season with a .711 OPS, his lowest in a full season, along with 19 home runs and 55 RBIs. Even with that dip, his glove stayed top-tier, and he added a career-high 41 stolen bases.

That swing in production means he won’t command the kind of contract he may have expected a year ago. Still, he remains one of the better position players available, and Spotrac projects a two-year, $34.9 million deal.

For San Diego, the appeal goes beyond the numbers. Chisholm will be 29 next year, and he would bring a jolt of energy to a roster that could use it. His speed would fit neatly into the way the Padres want to run offense, and his presence would add some life to Petco Park.

The main question is positional fit. Chisholm has played center field, second base and third base, but he is expected to stay on the infield. Center field is off the table in San Diego anyway, and third base is spoken for by Manny Machado for the foreseeable future.

That leaves second base, which would force the Padres to make a call on Jake Cronenworth. One option would be moving Cronenworth to first base if Ty France does not return, something the source makes clear would be a mistake. Another would be trading Cronenworth, though that would only make sense if a team was willing to take on the final four years and $50 million left on his deal.

Cronenworth is coming off the worst season of his career and will turn 33 in January. Swapping him out for a younger, more explosive player like Chisholm could give the Padres the kind of spark they need in 2027.

In Other News...

Preller Just Gave Padres Fans An Early Offseason Reality Check

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Preller also said the club wants to be more proactive in player acquisitions, which is exactly the kind of line Padres supporters will file away as they wait to see how aggressively the team operates. There were updates on reliever Jeremiah Estradas throwing program and outfielder Gavin Sheets injury management, and most of the coaching staff is expected back next season, though the exact shape of any staff changes still remains unclear. [Read more 🡒]

Padres Fans Have Every Right To Be Angry Over Manny Machado Snub

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Instead, Machado was left off the Gold Glove finalist list, with Alex Bregman, Javier Sanoja and Max Muncy getting the nod at third. The omission is a reminder that the award is not decided by advanced metrics alone, since manager and coach voting plays a major role alongside the SABR Defensive Index. For a player whose defense was strong enough to headline the position all season, the snub leaves San Diego with a fair gripe and a lingering question about how the voting process weighed his case. [Read more 🡒]

Padres Suddenly Have A Bigger Gavin Sheets Problem Than Expected

The Padres entered the winter expecting Gavin Sheets to be part of the conversation as a left-handed bench option, but his foot injury has introduced a new layer of uncertainty. While surgery is not expected this offseason, the real issue for San Diego is whether Sheets will be ready enough to count on when the season opens, or whether the club has to keep planning around his availability instead of his role.

That leaves the front office with a familiar kind of February problem: finding depth before it becomes a necessity. If the Padres want a safer left-handed bat on the bench, free-agent possibilities such as Nathaniel Lowe or Cedric Mullins offer more reliable health and offense on paper, which is why Sheets' status now matters more than it first did. [Read more 🡒]