Baseball Legend Reggie Jackson Talks Wedding Bells, Pitch Clocks, and Who Stopped Him From Buying His Own Team

Mr. October also predicts which team will win the 2023 World Series

March 22, 2023

Hall of Fame slugger Reggie Jackson came prepared when making his long-awaited Stern Show return on Wednesday morning. Not only did the charismatic baseball legend bring in a box of his own chocolate bars, but he also came equipped with fascinating stories about his incredible life, incomparable baseball career, and upcoming documentary, “Reggie.” The doc covers many of the 14-time All-Star’s on-field accomplishments, including the five World Series rings that earned him the nickname Mr. October. It also shines a spotlight on Jackson’s life outside the foul lines, which has at times been fraught with feuds and controversy. In his conversation with Howard, the former New York Yankees great and current executive assistant to the Houston Astros didn’t shy away from speaking his mind about challenges he’s experienced both within baseball — including one which prevented him from owning his own team — and away from it.

Reggie, who grew up near Philadelphia, felt the effect of racism at an early age. “Most of my friends were white,” Jackson told Howard. “That made a problem for me and my white friends because their parents did not want them to associate with me.”

His worst run-in with racist parents occurred at the age of 11 or 12 years old, when a friend lent Reggie his bike so he could make it home before dark. “I was riding home [and] his stepdad was coming up the street. He saw me riding the bike and he pointed to me to stop. He pulled over and told me to get off the bike and walk it back to the house,” Jackson recalled. “I never forgot that … I remember tears coming out of my eyes on the way home.”

The celebrated right fielder told Howard the experience shaped the man he would become. “I honestly think that it made me stronger. It made me so much more sensitive and aware of feelings – I can be in the room with a hundred people … and feel a racist on the other side of the room,” Reggie said.

The incident also continues motivating Reggie to this day, whether he’s helping underserved communities through the Mr. October Foundation or speaking openly about his experiences on the Stern Show. “This is a powerful way to help people through life,” he told Howard of their honest conversation. “How you’re expressing what you feel about me and how I’m responding to it is tremendous for people.”

Bud Blocked

Jackson made a name for himself as one of Major League Baseball’s best home run hitters in the late 1960s and early 1970s while playing for the Oakland A’s. He was traded away in 1976, but that’s not where his story with the franchise ended. When the A’s went up for sale in the early 2000s, he and a small group of investors — including multi-billionaire Microsoft co-founders Bill Gates and Paul Allen— attempted to purchase the ballclub.

“I sent a letter to Ken Hoffmann, who owned the A’s, [saying] ‘I’m willing to pay $25 million more than any bid you get,’” Reggie told Howard. He then had a conversation with M.L.B. Commissioner Bud Selig, who apparently assured him the sale was as good as approved. “He said, ‘Stay with me. I’ll guide you through [and] get this done for you — don’t worry about it,’” Reggie recalled.

“Then all of a sudden it turns out the A’s were sold to a guy named Lew Wolff — Bud Selig’s college buddy,” Jackson said. “It broke my heart. I went into a depression for about six months.”

Considering how Jackson’s candor had sometimes rubbed management the wrong way, Howard wondered if the other owners had conspired against him and prevented the sale.

“I absolutely believe that, and I absolutely believe Bud is the guy involved who denied me from getting the team,” Reggie said. He told Howard it even led him to draft a 100-page lawsuit along those lines, but he ultimately decided not to file it. “I got scared away by some people in baseball,” he said, explaining they told him he’d have to resign from his position with the Yankees and probably wouldn’t get hired again.”

“I should have sued, and I didn’t. It’s obviously still in my craw,” Jackson lamented, explaining there was still no reasonable explanation for why the league wouldn’t sell him a team when he was offering the most money and bankrolled by literal billionaires. “I could’ve bought the National League,” Reggie concluded with a laugh.

Stirring Drinks With Thurman Munson

Plenty of ink has been spilled about Reggie’s longtime rivalry with Yankees catcher Thurman Munson, but on Wednesday morning Mr. October finally set the record straight.

“Thurman Munson was a great guy,” Reggie said of his former teammate, who died tragically in an aviation accident in 1979.

According to Jackson, Thurman had encouraged Yankees owner George Steinbrenner to sign Reggie as a free agent. “He was part of the reason why I came [to New York],” Jackson said. However, the catcher’s opinion of him apparently changed after Steinbrenner gave Reggie a top-dollar contract but refused to bump Munson’s pay accordingly.

“Thurman and I had a meeting, and I told Thurman what I was making … and that was part of it,” Reggie said, explaining their rift only deepened after a reporter misquoted Jackson as having said “Munson thinks he can be the straw that stirs the drink, but he can only stir it bad.”

Their relationship was turbulent for a bit after that, but Reggie said the two eventually worked things out. “We patched up our differences and [got] together,” Jackson told Howard, revealing they grew so close he’d sometimes fly with Munson in his plane.

Wed October?

Mr. October may be done hitting home runs, but he can still go deep in matters of the heart. He opened up about his love life Wednesday morning, saying he’s in a relationship with a woman he’s known for about 30 years.

“She’s a tremendous friend. I love our life [and] spending time with her,” Reggie said, adding, “I’m not anti-marriage … I probably will get married.”

“There’s an exclusive!” Howard exclaimed. “Was it hard for you to open your heart to someone?”

“It wasn’t hard for me to open my heart, but it was hard for me to be loyal as a man. I cheated a lot,” Jackson admitted. “I won’t blame it on any excuse. I just cheated. I saw a pretty girl and I tried to sleep with her.”

He said past cheating had caused him to miss out on relationships with “a couple of wonderful ladies” in his life, but he’s learned his lesson and now he’s ready to focus on both his possible bride-to-be and his daughter from his prior marriage. “I have a wonderful daughter,” Reggie beamed. “What an unbelievable experience. She’s given me two grandchildren, two boys.”

Reggie’s Favorite Yogi Berra Quotes

Jackson crossed paths with countless Yankee legends over the course of his playing career, including Hall of Famers Joe DiMaggio, Mickey Mantle, Whitey Ford, and Yogi Berra. While many let their play on the field do the talking, he said Berra could always be counted on to deliver an unforgettable quip.

“Yogi probably said more than anybody, and he said it with Yogi-isms all the time,” Reggie said before sharing a locker room yarn from their playing days, which saw Yogi raving about his accommodations during a road trip to Chicago. “When we went to play the White Sox in the Windy City we stayed in the Regis Hotel … It was really nice,” Jackson said while in character as Yogi. “The only thing was the towels were so thick I couldn’t hardly get ‘em in my suitcase and get ‘em home.”

Reggie had anecdotes from after their playing days were over, too. He recalled once standing next to Yogi before an “old-timers” game as the scoreboard paid tribute to recently deceased ballplayers. “He’s putting his elbow in my ribs [and] says, ‘Boy, you know, I hope I don’t ever see my name up there,” Jackson remembered with a laugh.

Whoa, Whoa, Whoa – Start the Clock

Photo: Getty Images

Baseball has never been known for evolving quickly, but the sport underwent a major overhaul this season with the addition of a pitch clock, which limits the time in between pitches. Howard was curious if Reggie was a fan of the new pitch clock or if he was a baseball purist who preferred an old-school approach to the game.

“Old school is good, new school is good. Just remember: Your ass is always in school, no matter what you think,” Reggie joked.

In truth, Reggie was in favor of the pitch clock as well as fewer batter timeouts and pretty much anything else which might help with tempo. “The game needs to be sped up,” he said. “Three hours? Give me a break – that’s horrible!”

Who Will Win the 2023 World Series?

Howard was curious who Reggie believed would win the 2023 World Series. Jackson felt there were a handful of contenders, including the New York Yankees, the Atlanta Braves, the L.A. Dodgers, the Philadelphia Phillies, and his current team, the defending champion Houston Astros. He was less convinced by the New York Mets, however, and predicted their pitchers might struggle to stay healthy.

In the end, Reggie, one of the greatest hitters of all-time, told Howard great pitching would be the difference-maker this year. “We have the best pitching I believe in baseball,” Reggie said of his Houston ballclub. “And when you pitch, you don’t need a lot of offense.” “We’ll win 92 or 93 [games] and be [there] in the end, and if we get to the end we’re going to out-pitch you,” he continued. “If I’m going to pick a winner, I’m going to pick the Astros.”

Game Recognizing Game

Before signing off, Howard, co-host Robin Quivers, and Reggie exchanged very kind sentiments. “Reggie Jackson – listen, you’re the greatest,” Howard told his guest.

“It’s nice to be in company that I think is the greatest as well — and I’ve gotta give some props to Robin,” Jackson responded.

“You have no idea what this means to me,” Robin said.

“I will say that this is maybe my favorite interview, ever,” Jackson concluded. “I look forward to this again – and thank you very much.”

“Reggie” arrives March 24 on Amazon Prime Video.

You Give us your email Address we'll give you even more howard!

By signing up, I agree to receive newsletters and marketing emails from the Howard Stern Show and accept the Terms of Use and Privacy Policy