About the Off-Season: All That Jazz

About the Off-Season: All That Jazz

By Tim Kabel

December 13, 2025

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Other than a Rule 5 draft selection from the Cardinals and a bargain basement pitcher with no Major League experience, the Yankees did nothing at the Winter Meetings. By the way, yesterday, they sign ed a fellow named Drake Fellows, who is a pitcher to a minor league contract. Nothing else that we know of actually came to fruition. I don't believe Brian Cashman went to Disney World or the beach or anything like that. I think he was making efforts to improve the roster. I suspect he was laying the groundwork for future moves.

Hopefully, that is the case. Even more hopefully, the future will very soon become the present.

Every now and then, I get feelings about something. Frequently, it's a piece of pie or a cookie, or a snowstorm brewing but not always. I'm starting to get one of those feelings now. I'm looking at the various hints and clues that have been dropped recently. 

Brian Cashman has talked a lot lately about “challenge trades." That's a relatively new term. Originally, I thought it had something to do with duels, but it doesn't. It's when a team trades an established player to another team for their established player. An example of this was when the Yankees traded Don Baylor to the Red Sox for Mike Easler in 1986. The fact that Cashman is discussing challenge trades might be an indicator that the Yankees are looking to trade one of their veteran players for another veteran., or at least an established Major Leaguer.

Brian Cashman has also stated fairly often that the Yankees are too “left-handed”. He indicated a desire to even out the line up a bit. Currently, the left-handed batters in the Yankees lineup are Austin Wells at catcher, Ben Rice at first base, Jazz Chisholm, Jr. at second base, Ryan McMahon at third base and Trent Grisham in centerfield. Jasson Dominguez is not an established Major Leaguer yet and he is a switch hitter, so we can leave him out of the equation. Let's take a closer look at the players mentioned above.

Austin Wells could fit in the category of an established Major Leaguer and a left-handed batter who could be part of a challenge trade. Trading him would necessitate the Yankees moving Ben Rice behind the plate full-time. I have advocated this but only under the condition that the Yankees re-sign Cody Bellinger or someone else to play first base. In the someone else category, Pete Alonso has already gone to the Orioles. Munetaka Murakami is a corner infielder who has been posted and has a signing deadline of December 22nd, which is a little more than a week away. He is a left-handed batter, but I suppose it could work if the Yankees made other moves. Kazuma Okamoto is also a corner infielder and is a right-handed batter. His signing deadline is January 4th, 2026.

Ben Rice had a breakout year in 2025 but I wouldn't exactly call him an established Major Leaguer quite yet. He is on the cusp of becoming one. I also think the Yankees value him very highly and would be reluctant to trade him.

Ryan McMahon is a candidate to be traded but because of his offensive deficiencies, it might be a bigger challenge to find someone to take him in a challenge trade. I think he could very well be traded but he might only bring back a marginal Major Leaguer or some prospects.

Trent Grisham is on a one year $22 million contract because he accepted the Yankees’ qualifying offer. He could conceivably be traded. However, Grisham has an expensive contract and there are questions regarding his performance due to his postseason swoon and the fact that last year was the only year he was even really effective offensively. I don't believe he would bring much back in a trade.

That brings us to Jazz Chisholm, Jr.. Jazz joined the 30/30 club last year and has been a solid and somewhat flashy player for the Yankees since he arrived at the trade deadline in 2024. He has shown a willingness to change positions when asked.  I know some fans feel Jazz is a bit high maintenance and dramatic, but I don't have a problem with him at all. He plays hard and he plays well. However, he has one year left on his contract before becoming a free agent. The Yankees did not sign him to an extension after he arrived in 2024. I don't know if the team will attempt to sign him to an extension now or even if they have an interest in doing so. When Cashman was asked about the possibility of trading Chisholm, he described him as a “good get” and “above average”. He also said that the Yankees are open-minded when it comes to Jazz. That is not exactly a ringing endorsement.

The Yankees could trade Jazz for an established player and then sign Bo Bichette to play second base. Perhaps they will sign Bichette and Okamoto and trade Jazz and McMahon. That would bring in two right-handed bats. It would not replace Volpe. However, Volpe might not be able to return until May, at the earliest. That presents Jose Caballero with an opportunity to seize the position if the Yankees do not acquire another shortstop.

Think about it this way, if the Yankees went with Okamoto at third, Caballero at shortstop and Bichette at second base, as opposed to McMahon, Volpe, and Jazz, they would be less left-handed, and the overall salary difference might be tolerable for Hal Steinbrenner. How about if the Yankees traded Jazz to the Cardinals for Brandon Donovan. Donovan could play second, and Caballero and Okamoto could play shortstop and third base, respectively. There are a lot of different ways the Yankees could go.

Obviously, I'm not 100% sure certain but, my artificial hips have been aching a bit. That either means that there's a snowstorm coming, or Brian Cashman is about to trade Jazz Chisholm.