Howard Stern makes Reggie Jackson confess to women in his playing days: ‘I cheated a lot’

Trusting Reggie Jackson on the plate was one thing. Trusting him on the road was an entirely different thing.

Mr. October admitted to his womanizing while promoting an upcoming Amazon documentary about his life in an interview Howard Stern Wednesday.

“It wasn’t hard for me to open my heart, but it was hard for me to be faithful,” said Jackson, 76. “As a man, I cheated a lot.”

A powerful left-handed player who won three World Series championships with the Oakland Athletics and two more with the New York Yankees, Jackson’s Hall of Fame career was defined by his clutch hitting and uncanny knack for grabbing the media spotlight. He was also known to party at trendy clubs, such as Studio 54, where he was frequently involved with beautiful women.

“I wouldn’t blame him for any excuse,” he said. I just cheated. I saw a pretty girl and tried to sleep with her… I had access and took advantage of it. I’ve missed two wonderful women in my life, and that’s my fault.

Jackson was married once, but he and Jenny Campos divorced in 1973, while he was still playing for Oakland.

Refusing to make any excuses for his behavior in the ’60s, ’70s, and ’80s, Jackson appears to be a much different person now. He is currently in a relationship with a woman, and will likely end up getting married.

“She’s a great friend,” he said, “I love life and spending time with her.”

Jackson also has a daughter, Kimberly, from a previous relationship.

He said, “I have a wonderful daughter.” I was not married when I had her, but what an incredible experience it was, she gave me two grandchildren – two sons, and one of the children, the poor son, looks exactly like me.

Jackson would get a job as a special advisor to the Yankees after his playing career, and was even interested in becoming the team’s owner at some point.

But as he revealed to Stern, Jackson said then-MLB commissioner Bud Selig prevented him from buying the A’s in 2005 and instead turned the team over to one of his old college teammates.

As Jackson explained, a group of investors including Microsoft co-founders Bill Gates and Paul Allen planned to buy the team, offering $25 million more than the nearest offer. That should have been enough to seal the deal, Jackson said, adding that he “fully believes” that Selig intervened on behalf of his friend, Lew Wolfe.

“[Selig] He said, “Reggie, stay with me, I’ll walk you through, I’ll do it for you, don’t worry,” Jackson told Stern. Then all of a sudden, it turned out that the A’s had been sold to a guy by the name of Lew Wolff – Bud Selig’s college classmate.

Jackson was so upset with the sale that he nearly sued Major League Baseball, but was shut out by league insiders, in part, because he was concerned about being blackballed.

“I never introduced it,” Jackson said. I was afraid of some people in baseball. They said, “Reggie, the first thing you need to do is quit baseball, from the Yankees, and you’ll probably never get hired again.”

Wolf eventually bought the A’s for $180 million in 2005, but sold his shares over the years and stepped down as managing partner and co-owner in 2016.

Amazon’s documentary about Jackson, “Reggie,” premieres Friday on Prime.