Yankees’ Legend Leaves Astros Front Office; Could New York Bring Him Back?

Hall of Fame outfielder Reggie Jackson has left the Houston Astros after spending four years with the organization as a special advisor.

Mar 29, 2024; Houston, Texas, USA; New York Yankees designated hitter Giancarlo Stanton (right) talks with former player Reggie Jackson before the game against the Houston Astros at Minute Maid Park. Mandatory Credit: Troy Taormina-Imagn Images / Troy Taormina-Imagn Images

"Mr. October" has not been spotted much in the Bronx in recent years, but that could soon change.

On Friday, New York Post columnist Jon Heyman reported that Hall of Famer Reggie Jackson is leaving the Houston Astros after four years as a special advisor to owner Jim Crane. From 1993 until February 2021, Jackson held the same role with the Yankees, where he played five seasons, won two World Series titles, and saw his No. 44 retired.

Jackson, 78, told the Post he plans to spend more time with family in California after years of being a fixture at Astros spring training, select road trips, and behind the batting cages at Minute Maid Park on game days. However, he would not rule out a return to baseball or to New York, which Jackson said has "always been a home for me," adding, "I’m a Yankee. I’m still a Yankee."

The former 14-time All-Star and five-time World Series champion outfielder did not leave the Yankees on the best of terms in February 2021, saying in interviews that he felt he did not feel valued or listened to by people like general manager Brian Cashman.

“Nobody had any interest in what I had to say about free agents or about players or about the organization,” Jackson told The New York Post’s Jon Heyman and Joel Sherman on The Show podcast in April 2024.

Just months after his departure, he joined the Yankees’ bitter rivals in Houston, where he was given a greater voice in the decision-making process. As expected, some Yankees fans were not pleased to see Jackson in an Astros hat.

Despite everything that transpired, Jackson said earlier this year that he has a “family relationship with the Steinbrenners” and could “go back there tomorrow” if he chose. The Post reported that Jackson visited Yankees owner Hal Steinbrenner at a World Series game in New York last month.

There is no job offer on the table yet for Jackson, who oversaw five more championships as a member of New York's front office. However, the Yankees are reportedly not ruling out a return.

For now, Jackson’s focus is on spending more time with his daughter, three grandkids, and five siblings, four of whom are in their 80s.