BALTIMORE, MD – SEPTEMBER 21:  Jazz Chisholm Jr. #13 of the New York Yankees hits a solo home run in the tenth inning during a baseball game against the Baltimore Orioles at Oriole Park at Camden Yards on September 21, 2025 in Baltimore, Maryland.  (Photo by Mitchell Layton/Getty Images)

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Jackson Roberts

By Jackson Roberts

Contributing Sports Writer

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If the New York Yankees are going to trade Jazz Chisholm Jr., they need to nail the return.

Whispers that Chisholm could be traded started early in the offseason, and although the Yankees aren't desperate to move him, they've kept an open mind to that possibility, as MLB.com's Bryan Hoch reported on Monday. He's a very productive player, but he's one of many lefties in the Yankees' lineup, and with a year to go before he hits free agency, his best long-term value to the Yankees might be as a trade chip.

That theory only works, however, if the Yankees pick up pieces that get them closer to their ultimate goal of a championship, whether that skews toward the short term or within the next couple of seasons. Which teams might possess the capital to make such a trade worthwhile?

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BALTIMORE, MD - SEPTEMBER 21:  Jazz Chisholm Jr. #13 of the New York Yankees hits a solo home run in the tenth inning during a baseball game against the Baltimore Orioles at Oriole Park at Camden Yards on September 21, 2025 in Baltimore, Maryland.  (Photo by Mitchell Layton/Getty Images)

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Bleacher Report's Zachary D. Rymer proposed an interesting hypothetical on Wednesday featuring two very different players from the Cincinnati Reds.

In Rymer's proposal, the Yankees would send Chisholm to the Cincinnati Reds for starting pitcher Brady Singer and second baseman Matt McLain, who constitute a very interesting balance of floor and ceiling.

"Whereas Singer is part of a pitching surplus in Cincinnati, he'd probably be the Yankees' No. 3 starter out of the gate if he were to land in New York," Rymer wrote. "He isn't going to be any more than that, but he would at least promise to give them innings at the back end of the rotation as the year went along.

"McLain would essentially be a lottery ticket for the Yankees. He'll be two years removed from shoulder surgery in March, and the hope would be that he can be the same guy who hit .290 and racked up 3.6 rWAR as a 23-year-old in 2023."

Singer, who has made 32 starts in each of the past two years, pitched to a 4.03 ERA this year, which equated to 3.1 rWAR. He's dependable, but he'll be a free agent in a year as well, so he's no more sustainable a piece than Chisholm.

That's why the Yankees' thoughts on this deal would hinge on McLain. He looked like a future star two years ago, and if New York believed his shoulder was hampering him this past season and would not be a factor moving forward, it would be appealing to swap out Chisholm for a replacement with four years of control.

As a thought exercise, this hypothetical deal is fascinating. In practice, though, we have no idea if it's on the table for either side.

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