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Charles Barkley and Madonna: the ’90s Couple That Never Was

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Inside a juicy rumor that just refused to die.

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As Charles Barkley embraced Oliver Miller and Tom Chambers walking off the court in Game 7 of the 1993 Western Conference Finals, NBC announcer Dick Enberg noted the unbridled happiness of the sport’s antihero, musing that for as angry as Charles could get at times, his smile was so electric that it could power the city. No one on the Seattle SuperSonics could contain Charles. He finished with 44 points and 24 rebounds, shooting 12-of-20 from the floor and 19-of-22 from the free throw line in forty-six minutes.

“I tell people that 44–24 game is probably the best game I ever played in my life,” Charles said in 2018.

Phoenix’s 123–110 win over Seattle had Suns owner Jerry Colangelo in tears, his team going for its first title in the franchise’s silver anniversary season. Amid the handing out of purple T-shirts, Kevin Johnson couldn’t stop smiling, saying the win was “like I’ve dipped my hand in a honeycomb and tasted something sweet.” Miller was hoarse. Chambers was rejuvenated. Danny Ainge was beat up, but ready for the fight that awaited. Though he was already looking ahead to Chicago and all the golf he was going to play with Michael Jordan, Charles’s more pressing matter was obtaining a six-pack to drink in his Jacuzzi. After the game, he walked over to backup point guard Frank Johnson.

“He said, ‘Frank, I told you not to worry about it,’” the backup guard recalled decades later.

The day before the game, Jordan had called him to wish him luck and urged him to take the ball to the hoop over and over again. Now he’d see him soon. But Charles got another call the night before from someone who was about to be linked to him for reasons other than basketball.

Madonna.

Read more about Barkley in Timothy Bella’s new biography.

Courtesy of Hanover Square Press

An avid soccer fan, chef Tony Hamati only started liking basketball because of Charles Barkley—but the free tickets to the games didn’t hurt either for the star’s favorite Italian restaurant manager. “When they’d score, I’d yell, GOOOOOOOOOAAAAAAL!” Hamati recalled. “That night, Charles came in and said, ‘This is not soccer.’ I told him it was the same thing.”

After he cooked for King Hussein of Jordan, the royal family funded the continuation of Hamati’s culinary training at the Culinary School of the Sorbonne in Paris. Arriving in Phoenix in 1985, Hamati quickly became one of the premier culinary figures in the Valley. As manager at Tomaso’s, the intimate Italian hotspot near Camelback Mountain, Hamati’s big personality suited his high-profile patrons. Hamati took a shine to Charles from the first time Colangelo brought him into Tomaso’s.

One night in late May 1993, Charles introduced Hamati to a woman the chef had never expected to meet.

“He stuck his head in and said, ‘Tony, this is Madonna,’” the chef remembered. “She didn’t look like Madonna, but it was actually her.”

While it’s unclear how Charles and Madonna connected, they had kept in touch in the weeks leading up to the playoffs. She was even spotted courtside with comedian Rosie O’Donnell and late-night host Arsenio Hall during one of the Suns’ playoff games against the Lakers in early May. Hall recounted years later that it was something of an unannounced double date-type setup. “Charles Barkley was Madonna’s date and I was Rosie’s date,” Hall recalled years later to VladTV, still surprised by the arrangement.

Her public infatuation with Charles came through in an interview that year with O’Donnell, her friend and co-star in “A League of Their Own,” in Mademoiselle magazine. The Q&A, which included the pop star asking the comedian whether getting your period or watching an episode of the daytime talk show Sally was more annoying, had Madonna pose another question to O’Donnell. If you could have your choice, who would you pick to father your child: Denzel Washington, Damon Wayans, or Charles Barkley? O’Donnell picked Wayans, saying he was the funniest and cutest to her. When she turned the question around on her friend, Madonna came to a different conclusion.

“Charles Barkley is God,” Madonna said. “Denzel Washington is married, and you know what? I think Charles is probably married. See, all the good ones are taken…but that doesn’t mean they can’t father your children!”

After the dinner, it wouldn’t take long for the media to approach Hamati, including Inside Edition and Entertainment Tonight. He claims he was offered $50,000 to spill on TV about Charles and Madonna at his restaurant. The manager had already seen a couple of the reports that framed the flirtatious couple as having played footsie, which he thought was fabricated. When speaking to Ann Gerhart in her “Tattler” column for the Philadelphia Daily News, Hamati denied seeing them altogether. He turned down the money offered to tell the story, even if there wasn’t a lot to tell, out of what he said was loyalty to his customer and friend.

All of this was playing out right before Charles and the Suns faced off against Jordan’s Bulls. A manager with The Roxy, a popular Phoenix nightclub, told the Phoenix New Times about how the pair danced the night away and hung out at a roped-off section. (Charles maintained that the reports were false, saying he had never shared dance moves with Madonna.) Unsubstantiated reports of Charles’s limo being parked overnight outside her hotel filled newspapers.

The pop star played coy about the details of the alleged tryst, replying, “Who’s Charles Barkley?” Outlets couldn’t help scrutinize the potential pairing. “She’s awfully short. He’s awfully married. He’s said he’s an emotional man, can’t open his eyes when he makes love. We know she’s a voyeur, can’t keep her eyes closed when she makes love,” Gerhart wrote in “Tattler.”

“He may retire; she’ll never retire. She’ll be stripping in the old-age home.”


Amid Barkley’s incredible season, rumors swirled around his love life. Charles and wife Maureen were separated at the time, and the reasons were never made public.

There was a separate matter in which gossip columnists reported how Connie Colla, the morning news anchor with Phoenix’s NBC affiliate, had been seeing Charles. Years later, Colla maintained that was never the case. The two were working with each other on the weekly Suns show, and a couple times each month, they would shoot stories about everyday life and goofy bits, such as, “What if Charles had hair?” featuring Barkley in a mohawk or Princess Leia buns. They had grabbed lunch one day as they often did, but this time, a gossip entry reported them as having an “intimate lunch.” The Montana native called Charles to see if he was rattled. He wasn’t. “Listen, Montana, when you’re in the spotlight, people are going to say all kinds of things about you. As long as they spell your name right, it’s all good,” he said to her, she recalled. “It means you’re important enough to sell their paper.”

But those two lines ended up changing everything for Colla. The rumors had hit a point where she had to end the friendship with him, and hasn’t spoken to him in nearly twenty years.

“After a while, it became obvious people really believed this, so I told Charles, ‘This is nuts.’ I’d never in my life told someone to go away and not be my friend, it was really painful,” Colla recalled. “I think he was stunned by it, too.” Through it all, Charles became the most popular athlete the city had ever seen. At 62–20, the league’s best record, Charles, the league’s MVP, had given the team and Phoenix exactly what it needed at exactly the right time. And now it called for a championship.

But the headlines and gossip columns took a toll. Speculation surrounding Charles and Madonna had become so constant that Ellen Blumhardt, his mother-in-law, had suffered a heart attack. “She has had a lot of stress from the jokes about me and Madonna [dating] and has been harassed with people calling the house. She’s not doing well right now and that’s a major concern,” he told reporters of the heart attack, which appeared to have happened the same day as Game 7 against Seattle. “I only met [Madonna] one time when she was in Phoenix. We don’t date. We don’t have a relationship.”

For the first time, Charles said he felt how bright and hot the limelight was for stars like Jordan and Magic Johnson. Through the Madonna coverage, Charles also got a taste of what it was like for Jordan to block out the media entirely after his gambling habits had been called into question. Charles, who admitted to being telephone pals with Madonna, would say the questions about her didn’t bother him, not when he had more pressing matters at hand. Yet there was something about her celebrity he admired.

“I’m going to be on NBC at least four times, and Madonna won’t be,” he said ahead of the Finals. “I’ll get more pub than her. Of course, she’s got her movies. I’ve got to win a ring first, then I can make a movie. I’m on a mission.”

The story of Mad-Char eventually faded, but it resurfaced less than a year later during Madonna’s legendarily contentious interview with David Letterman.

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The plan was for Madonna to hold Letterman’s feet to the fire on some of the jokes he had made at her expense. By the time she arrived at the Ed Sullivan Theater, however, Madonna had already smoked a joint, she later admitted. Unbeknownst to the public, she was privately dating rapper Tupac Shakur, who she said had her riled up about life when she stepped on stage in a floor-length black dress and combat boots for The Late Show with David Letterman.

The interview featured Madonna saying “fuck” fourteen times in what became probably the most-censored late-night broadcast in television history. Madonna, who said Charles did not understand “the meaning of friendship,” gave suggestive answers throughout the memorable segment.

Charles said to reporters he didn’t see the Letterman interview, but was curious.

“What did she talk about?” Charles asked a radio host.

“You,” the commentator replied.

Charles could only offer a one-word answer: “Good.”

Adapted from Barkley @ 2022 by Timothy Bella, used with permission by Hanover Square Press.

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