Inside The Pinstripes

Yankees Dropped The Ball With Kyle Tucker

The New York Yankees made a mistake in the Kyle Tucker sweepstakes.
May 1, 2025; Pittsburgh, Pennsylvania, USA;  Chicago Cubs right fielder Kyle Tucker (30) circles the bases on a solo home run against the Pittsburgh Pirates during the fifth inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
May 1, 2025; Pittsburgh, Pennsylvania, USA; Chicago Cubs right fielder Kyle Tucker (30) circles the bases on a solo home run against the Pittsburgh Pirates during the fifth inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

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The New York Yankees were never among the main clubs in the mix for Kyle Tucker's services in free agency, instead residing on the periphery at best, but that's exactly their problem in this situation.

In what appeared to be shaping up as a battle to land the four-time All-Star outfielder between the Yankees' two rivals in the Toronto Blue Jays and New York Mets, it was the back-to-back World Series champions Los Angeles Dodgers who arose from their brief slumber and inked Tucker to a four-year deal worth $240 million.

Signing Tucker wasn't a necessity for the Yankees, especially given their ongoing negotiations with Cody Bellinger, but their seeming lack of true interest in the former was puzzling and has put them at a disadvantage.

Chicago Cubs right fielder Kyle Tucker
Oct 9, 2025; Chicago, Illinois, USA; Chicago Cubs right fielder Kyle Tucker (30) reacts after hitting a home run against the Milwaukee Brewers during the seventh inning for game four of the NLDS round for the 2025 MLB playoffs at Wrigley Field. Mandatory Credit: David Banks-Imagn Images | David Banks-Imagn Images

Why Yankees Messed Up with Tucker

The Yankees' miss on Tucker has extended their streak of missing out on premier position player free agent targets, which has become a constant theme over recent years.

This was a unique case to be uber-aggressive considering where Tucker's market landed, and who is to say whether or not the Yankees would have had a real chance to add him over the Dodgers, but we'll never know the answer to that question.

For many years now, the Yankees haven't necessarily operated like the Yankees of old. Sure, they still carry one of the top payrolls in the game and are perennial playoff contenders, but it's a far cry of the version of the club that existed in the late 1990s and early 2000s that was winning World Series left and right.

The Yankees are likely thanking their lucky stars that Tucker ended up in Los Angeles instead of Toronto since it keeps the path to an AL East title and AL pennant less convoluted, but that line of thinking becomes a bit peculiar when you realize that they could've just pursued the star outfielder themselves and paired him with Aaron Judge.

Yankees Now Need Bellinger

The Yankees' outfield is in good shape with Judge, Trent Grisham, Jasson Dominguez and even Spencer Jones, but they have remained in contract negotiations with Bellinger over recent days.

Again, the Yankees don't necessarily need Bellinger in order to feel good about where they stand at this point of the offseason, but bringing him back would qualify as a strong response to the Dodgers and keep them afloat as a potential contender to take them down in the Fall Classic this year.

If Bellinger heads elsewhere, there's no clear pivot for the Yankees, which is a sobering thought for the club.

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Jack Markowski
JACK MARKOWSKI

Jack is a New Jersey native who graduated from the University of Pittsburgh as a Media & Professional Communications major in 2024 who is now covering the Pittsburgh Steelers and New York Yankees for On SI.