Mr. October points finger at Yankees for his Bronx departure, keeps the door open

Yankees legend Reggie Jackson is with Gerrit Cole at Yankee Stadium in 2023.

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Reggie Jackson, a legendary figure forever linked to the New York Yankees with his “Mr. October” nickname, finds himself in a situation with divided loyalties. Since May 2021, Jackson has served as a special advisor to Houston Astros owner Jim Crane. This affiliation naturally creates some conflicting emotions when the Yankees face the Astros.

Despite his new role with the Astros, the Yankees remain a team deeply ingrained in Jackson’s baseball journey. With the Yankees, he experienced some of his most iconic moments, solidifying his place in baseball history. However, in February 2021, Jackson’s relationship with the Yankees came to an end after serving as an advisor for nearly three decades. His decision to depart stemmed from a perceived lack of value placed on his experience and insights by the organization.

Jackson recently elaborated on his reasons for leaving the Yankees during an appearance on “The Show” podcast, hosted by New York Post writers Jon Heyman and Joel Sherman. He specifically mentioned feeling disregarded when offering his input on free agents, player development, and overall organizational direction. This sense of being undervalued ultimately led him to pursue a new opportunity with the Houston Astros.

Reggie Jackson unhappy to leave the Yankees


According to Jackson, the decision to leave the Yankees had been brewing “for a couple of years.” He felt his role within the organization gradually diminishing and expressed a desire for a more substantial say in long-term strategy. Jackson envisioned himself contributing to identifying potential replacements for players like Gleyber Torres at second base, ensuring a smooth transition in the future.

Conversations with Yankees general manager Brian Cashman proved frustrating for Jackson. He felt his perspectives on roster decisions and minor league development weren’t being given due consideration. While not seeking absolute power, Jackson yearned to contribute his vast experience and insights to the team’s success.

Despite his departure, Jackson’s legacy with the Yankees remains undeniable. During his five-year tenure as an advisor, they secured two World Series championships, adding to his own impressive tally of five rings. He also secured a second World Series MVP title in 1997, further solidifying his place in Yankee lore. Jackson’s regular-season statistics boast a commendable .281 batting average, 144 home runs, and 461 RBIs, further etching his name in the team’s record books.

Manager Aaron Boone with ex-Yankees great Reggie Jackson at Yankee Stadium.

In contrast, Jackson finds his role with the Astros to be more active and fulfilling. Working under owner Jim Crane, he appreciates the organization’s focus on winning and its commitment to an inclusive leadership style that values diverse perspectives. Jackson highlights Crane’s respect for individuals, something he values greatly.

Interestingly, Jackson emphasizes that his relationship with the Steinbrenner family, the Yankees’ owners, remains strong. He describes it as a “family relationship” and acknowledges the possibility of returning to the Yankees someday. This enduring bond underscores the multifaceted nature of his baseball journey and the lasting impact he’s had on both franchises.

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