Why Chicago Cubs Should Explore a Pillow Contract with Jazz Chisholm Jr.

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Jazz Chisholm Jr. had a tough final season with the New York Yankees. The svelte second baseman stole 41 bases, but his strikeout rate climbed, his OPS dropped by over .100, and when the campaign ended, the Yankees elected not to extend him a qualifying offer. A year or two ago, he looked like one of the marquee prospective free agents of the 2026-27 class. Now, he's unlikely to get a big payday this winter.

For the Chicago Cubs, though, that might all be good news. Both Seiya Suzuki and Ian Happ are free agents, and neither is particularly likely to return. The Cubs therefore need to make some major investments in the corner outfield market, but they can't afford to sign such a player to a long-term, high-dollar deal. Chisholm might just be the perfect fit for the team, on what would be a short-term deal with upside both ways.

In November 2022, the Los Angeles Dodgers non-tendered Cody Bellinger. The former National League MVP had fallen a long way in a short time, after separate injuries to his knee and shoulder hampered him and resulted in ugly offensive stat lines in 2021 and 2022. Bellinger's talent was still evident, but given his two-year slump and the big payday that would have avaited him in a final trip through arbitration, it was no big surprise that the Dodgers cut him loose.

The Cubs swooped in not long afterward, though, signing Bellinger to a one-year, $17-million contract that would turn out to be a boon for the player and a bargain for the team. On the North Side, Bellinger rediscovered his form and became a key cog in the team's resurgent lineup. When he hit free agency again the next winter, the sides got together again, on a more lucrative (but still short-term) deal that included an opt-out after 2025. It might be the best signing of the Jed Hoyer Era, on a strict value basis.

You can see where I'm going with all this. It's possible that Chisholm, who will turn 29 years old next February, will push for a long-term deal this month, while he's unencumbered by the qualifying offer. If, however, he's open to a flexible short-term deal whereby he would move to left field and try to establish a much better platform for a second run at free agency, the Cubs should be all over the opportunity.

Of course, that would represent a position switch for the Bahamian star, and it'd be a big move down the defensive spectrum. He came up as a second baseman, then moved to center field for a spell, and he's been back on the infield since the Yankees acquired him two and a half years ago. He rated very well at second base in 2026, too, according to Outs Above Average. In fact, his glovework at second is the only thing that kept him near star level this season, going by those numbers. But those numbers are liars. Chisholm's defense was solidly below average, according to Defensive Runs Saved (DRS) from Sports Info Solutions. He posted -6 DRS at the keystone this year, with poor range (especially to his right). When you watch him on tape, it's easy to tell which stat is right. Chisholm is not a plus defensive infielder.

He also wasn't a good defender in center field, but that was a while ago, and the Cubs don't need him to be a center fielder. In left field, Chisholm profiles quite well. Some of the best plays he made at second in 2026 even came on balls hit in the air, over his head. He might not be eager to make the change, but a move to an outfield corner would be good for his defensive value. It would also give him a chance to focus on fixing what went wrong at the plate in 2026.

In a nutshell, what went wrong at the plate was that the lefty swinger got pull-happy. After hitting 31 home runs in his first full season with the Yankees, Chisholm tried to produce even more power in 2026, and he ended up rolling over far too often. A whopping 27.7% of his batted balls were pulled on the ground, which was not only the highest share of his career, but the sixth-highest among the 274 batters who had at least 200 total batted balls in 2026. It was a waste of Chisholm's speed, and it also led to his increased strikeout rate.

On balance, he's still a dynamic offensive player. He stole 41 bases in 50 tries and hit 19 home runs. He drew 56 walks. To get back to the level of production of which everyone agrees he's capable, though, Chisholm will have to retreat a bit from his all-or-nothing approach. He's exactly the kind of hitter with whom John Mallee routinely does good work; he would thrive in the Cubs' hitting system.

A true one-year deal is unlikely, but there might be common ground on a structure whereby the Cubs guarantee Chisholm up to $60 million, but give him the chance to opt out of most of that and return to free agency after 2027 or 2028. If Chisholm is open to that, the Cubs should give it a whirl.

The final question would be about the player's makeup, and it's a legitimate one. Chisholm's play is stylish, but it often looks flippant, and he's rubbed multiple sets of teammates and coaches the wrong way. It's somewhat telling that the Yankees didn't extend him the QO, letting him leave for nothing. There's no question that Chisholm is a different kind of person than Alex Bregman, Dansby Swanson or Nico Hoerner. That's not necessarily a bad thing, though. The Cubs need a bit more varied a set of personalities in the clubhouse. They need some looseness and swagger to balance what is a tightly wound, very intense team. Chisholm might benefit, too, not only from interacting with the serious professionalism of Swanson and Bregman but from Pete Crow-Armstrong's combination of cocksure and intense.

Chisholm is the player whose talent outstrips his likely cost by the most this winter. There are reasons for that, but the Cubs need to be open to the idea that those reasons are market inefficiencies, rather than ironclad condemnations of Chisholm. He might be the player who can galvanize their team and leave room for all the rest of the work they need to do this offseason.