Inside The Pinstripes

Yankees Insider Calls Out Frustrating Offseason

This New York Yankees insider is beyond frustrated with the team's quiet offseason.
Aug 15, 2025; St. Louis, Missouri, USA;  New York Yankees manager Aaron Boone (17) looks on from the dugout before a game against the St. Louis Cardinals at Busch Stadium. Mandatory Credit: Jeff Curry-Imagn Images
Aug 15, 2025; St. Louis, Missouri, USA; New York Yankees manager Aaron Boone (17) looks on from the dugout before a game against the St. Louis Cardinals at Busch Stadium. Mandatory Credit: Jeff Curry-Imagn Images | Jeff Curry-Imagn Images

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It has been literal months since the New York Yankees have made a major move in the organization. Yankees fans are fed up, and rightfully so having waited since July for a move to be made.

Even with the ongoing Cody Bellinger contract talks, that doesn't make up for the lack of moves that have happened elsewhere. Bellinger doesn't keep this team running, and the 27-time World Champs would be just fine without him.

During all of this, the Yankees have lost out on key free agent signings time and time again. There's a world where they enter the 2026 season with a worse roster than the year prior, something that didn't even seem possible.

Yankees insider Stanzo recently discussed their horrible offseason and where they've went wrong with all of these free agents. He raises some great points, and it's well worth a listen for any Yankees fan who expresses the same frustration.

Yankees Can't Be Afraid To Spend Money

"If you give a free agent a fair offer, prepare to finish in third place for that free agent," Stanzo said. "You're going to have to get a little bit uncomfy to get these coveted guys who are at the top of the sport.

He continued, "When you look at the end of the season and who's coming up big in crucial playoff and World Series games, it's these guys. The Ohtani's, the Vladdy's, the Judge's."

"The Yankees have a chance to acquire one of these guys in his 20's after they didn't try for Harper and Machado, they don't go for Seager, they don't go for Freddie Freeman, they try and miss on Juan Soto, it's not very often these guys come available."

Kyle Tucker Linked To Yankees

Kyle Tucke
Oct 2, 2025; Chicago, Illinois, USA; Chicago Cubs designated hitter Kyle Tucker (30) celebrates with teammates after scoring during the second inning against the San Diego Padres during game three of the Wildcard round for the 2025 MLB playoffs at Wrigley Field. Mandatory Credit: David Banks-Imagn Images | David Banks-Imagn Images

Stanzo finished the clip by saying "it makes no sense the Yankees aren't even entertaining the idea of Kyle Tucker," which raises a valid point. After they were finally linked to Bo Bichette, only can only imagine what other names they could've been linked to all this time had they actually tried to make something happen.

Tucker spent the majority of his career in Houston before joining the Chicago Cubs. He's coming off a solid all-around season and could be a valuable outfield asset should Bellinger and the Yankees decide to go their separate ways. Even if they're able to bring Bellinger back after all of this, they could ultimately end up just trading him anyways should they smarten up and realize Tucker has been the better option all along.

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Jordon Lawrenz
JORDON LAWRENZ

Jordon Lawrenz is a writer for On SI, part of the Sports Illustrated Network. Jordon is an accomplished writer for NFL, MLB, and college football/basketball. He contributes to PFSN’s and Heavy’s NFL coverage. Having graduated from the University of Wisconsin - Green Bay with a Sports Communication and Journalism degree, Jordon fully embraced the sports writing lifestyle upon his relocation to Florida.