Howard Stern gets Reggie Jackson to admit to womanizing in his playing days: 'I cheated a lot'

Trusting Reggie Jackson at the plate was one thing. Trusting him on the road was something different, entirely.

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

‘It wasn’t hard for me to open my heart, but it was hard for me to be loyal,’ said the 76-year-old Jackson. ‘As a man, I cheated a lot.’

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

‘I won’t blame it on any excuse,’ he said. ‘I just cheated. I saw a pretty girl and I tried to sleep with her… I had access and I took advantage of it. And I missed a couple of wonderful ladies in my life and it’s my fault.’

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

Refusing to make any excuses for his behavior in the 1960s, 70s, and 80s, Jackson appears to be a much different person now. He’s currently in a relationship with a woman, whom he will ‘probably’ end up marrying.

‘She’s a tremendous friend, I love the life and spending time with her,’ he said.

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

‘I have a wonderful daughter,’ he said. ‘I wasn’t married when I had her, but what an unbelievable experience, and she’s given me two grandchildren — two boys, and one of the kids, the poor son of a gun, he looks just like me.’

Jackson would take a job as a special advisor to the Yankees following his playing career, and was even interested in becoming a team owner at one point.

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

As Jackson explained, a group of investors including Microsoft founders Bill Gates and Paul Allen planned to buy the team, and offered $25 million more than the nearest bid. That should have been enough to get the deal done, Jackson said, adding that he ‘absolutely believed’ Selig intervened on behalf of his friend, Lew Wolff.’

‘[Selig] said, ”Reggie, stay with me, I’ll guide you through, I’ll get this done for you, don’t worry about,” Jackson told Stern. ‘Then all of a sudden, it came out that the A’s were sold to a guy by the name of Lew Wolff — Bud Selig’s college buddy.’

Jackson was so upset over the sale that he nearly sued Major League Baseball, but was talked out of it by league insiders, in part, because he was worried about being blackballed.

‘I never filed it,’ Jackson said. ‘I got scared away by some people in baseball. They said, ”Reggie, the first thing you’ll have to do is resign from baseball, from the Yankees, and you probably won’t get hired again.’

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

Amazon’s documentary about Jackson, ‘Reggie,’ premiers Friday on Prime.