Inside The Pinstripes

Yankees Must Prepare for Disappointing Outfield Possibility

Everything still feels possible for the New York Yankees, but they need to prepare for a disappointing possibility with two free agent outfielders.
Oct 2, 2025; Bronx, New York, USA; New York Yankees catcher Austin Wells (28) and outfielder Cody Bellinger (35) shake hands following game three of the Wildcard round for the 2025 MLB playoffs against the Boston Red Sox at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images
Oct 2, 2025; Bronx, New York, USA; New York Yankees catcher Austin Wells (28) and outfielder Cody Bellinger (35) shake hands following game three of the Wildcard round for the 2025 MLB playoffs against the Boston Red Sox at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

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The New York Yankees' slow offseason is worrisome, and while there is plenty of time left, the team needs to prepare for the possibility that they miss out on at least one of their top targets.

Rumors are circling that Scott Boras, a sports super agent who represents Cody Bellinger and pitching target Tatsuya Imai among many others, may wait until free agent outfielder Kyle Tucker inks a deal before he makes a commitment with Bellinger. This should concern the Yankees for multiple reasons.

Brendan Kuty of The Athletic shared the news from a source that Boras might wait it out, and MLB's Bryan Hoch recently suggested in a Reddit AMA that the Yankees should prepare for the real possibility that they could lose Bellinger in free agency. After his banner season in pinstripes, Bellinger would be a serious loss, and the waiting game would mean the Yankees lose out on Tucker as well.

Originally floated as a backup plan for the Yankees if they can't land Bellinger, the conversation about pursuing Tucker seems to have subsided since the recent MLB Winter Meetings, and they seem unlikely to chase the more expensive slugger first over their reunion with a superior defender.

What if the Yankees Lose Both?

New York Yankees left fielder Jasson Dominguez
Aug 22, 2025; Bronx, New York, USA; New York Yankees left fielder Jasson Dominguez (24) catches a fly ball hit by Boston Red Sox first baseman Nathaniel Lowe (37) (not pictured) during the ninth inning at Yankee Stadium. Mandatory Credit: Gregory Fisher-Imagn Images | Gregory Fisher-Imagn Images

All that said, if the Yankees lose both sluggers, they don't seem to have a clear pivot. The current options are Jasson Dominguez and Spencer Jones, neither of whom can quite hold a candle to the stronger options at the moment.

Jones' strikeout rate in the minors would be the highest in the majors if they do promote him, and Dominguez is not the left fielder they need out there, with -10 outs above average placing him in the second percentile among defenders. Both young men are expected to improve with time and, according to Cashman, have earned a shot at the position if the opportunity is there, but it leaves the Yankees in a tight spot.

New York Yankees second baseman Jazz Chisholm Jr.
Oct 2, 2025; Bronx, New York, USA; New York Yankees second baseman Jazz Chisholm Jr. (13) runs of the field between innings during game three of the Wildcard round for the 2025 MLB playoffs against the Boston Red Sox at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

Both Jones and Dominguez are trade possibilities as well, and the Yankees aren't ruling anything out in a nebulous offseason that has fans baffled so far. They might also trade Jazz Chisholm Jr., and while speculation suggests they would prefer to trade for a starting pitcher rather than pick one up in free agency, the Yankees may ultimately choose to flip the script there, picking up a free agent starter like Tatsuya Imai and trading for a powerful outfield bat.

All that said, they are unlikely to do much better than the two free agents on the table, and the market is tightening quickly.

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Published
Erin Shapland
ERIN SHAPLAND

Erin covers the New York Yankees for On SI, reporting on all aspects of the championship chase that comes with a storied franchise. A fan of all storylines, who's looking to bring the latest news and updates to one of professional sports' greatest fanbases.