The Hidden Truth Of Dennis Rodman

Dennis Rodman carries a cultural cache that extends well past his 20-year career as a professional basketball star. Indeed, the eccentric celebrity oddly nicknamed "The Worm" is known as much for being one of a few weird basketball stars off the court as he is for winning five NBA championships with the Detroit Pistons and the Chicago Bulls. But for all the icon has done — in sports or otherwise — there are still several areas of Rodman's quirky and challenging existence that even diehard fans may not know about.

Undoubtedly, most with a firm grasp on Rodman's life and career can list some of his more widely reported highs and lows. For example, some might recall Rodman's infamous trip to Las Vegas amid the 1998 NBA Finals, when he went missing in action after overstaying his allotted timeframe for his time in Sin City.

Fans also likely know about one of Rodman's lowest points in February 1993, when the Pistons star was found by police carrying a loaded rifle in his vehicle amid a welfare check outside the team's home stadium in Michigan, as detailed in his 1996 memoir, "Bad as I Wanna Be." But there is much more to Rodman — a hidden truth to the sports icon that informs his character as one of the most distinctive celebrities to ever grace pop culture.

Like anyone coming into a newfound fortune, Dennis Rodman had to navigate his way through wealth after he was selected by the Detroit Pistons in the 1986 NBA draft. By the 1988-89 season, he was pulling in a salary of $550,000 — roughly $1.5 million in 2024 dollars. That figure only went up as his playing career continued.

How did Rodman respond to the money? For one, he started opening his wallet to those less fortunate. In true Rodman fashion, however, he did it in his own unique way: he began handing out cash to the unhoused people he would see on the street. His generosity was best exemplified by the kindness he showed to a pregnant woman, who asked him for spare change for food as he was walking back from a restaurant.

"I had $250 in my pocket, and I gave it all to her,” Rodman told The New York Times in 1990. ”If I had $1,000, I would have given her that, too. There are a lot of people out there that are more worthy of this money. People without houses. People living on the street. I was lucky to come upon this — what I have now." He added, ”I gave a lot of money to the homeless this year. I go to downtown Detroit and give out $50 bills or $100 bills. You can't help everybody, but you can help some people.”

Dennis Rodman showed the world he enjoyed dressing up like a woman when he arrived at a 1996 event promoting his book "Bad as I Wanna Be" in a luxurious, French-made wedding dress. Saying he was bisexual and claiming he was marrying himself, he traveled to the promotional stop at a New York Barnes & Noble in a horse-drawn carriage. It wasn't the first or last time Rodman would publicly wear women's clothing — a year earlier, he donned a sparkly women's top to the 1995 MTV Video Music Awards.

But Rodman's cross-dressing goes back even further than that, all the way back to his childhood. In his autobiography, the star divulged that it began by playing dress-up as a youth, and he connected that lineage to the flamboyant outfits he would curate throughout his public career.

"I grew up around women, and as a kid I would sometimes dress up as a girl," Rodman writes in "Bad as I Wanna Be." He explains, "You play house, you play doctor — everybody does that, but some people like it more than others. You play by dressing up and acting like a woman. I think a lot of kids have done that. I used to go through the whole routine — dress up, wear makeup, act like a girl. When I cross-dress now, it's just another way I can show all the sides of Dennis Rodman. I'm giving you the whole package."

Even on the eve of an NBA championship, it wasn't all wine and roses for Dennis Rodman. During the 1997 NBA Finals, when the Rodman-imbued Chicago Bulls faced the Utah Jazz, Rodman received the NBA's then-biggest-ever player penalty — $50,000 — for twice disparaging Mormons in expletive-laden remarks. Utah has the highest Mormon population of any U.S. state, and Rodman evidently had qualms with how that was represented in the stands.

Before the NBA announced the fine, Rodman had already publicly apologized. Still, the then-commissioner of the league, David Stern, came down hard on Rodman with the monetary punishment. Of course, Rodman was no stranger to controversy that caused significant backlash — earlier that same season, he'd been suspended for 11 games and fined $25,000 – the maximum NBA fine at the time — for kicking a courtside camera person. But his remarks directed towards Mormons got him in even bigger trouble.

”I have indicated in previous actions that insensitive or derogatory comments involving race or other classifications are unacceptable in the NBA,” Stern said in a press release when the NBA announced the penalty. ”Dennis Rodman's comments were exactly the kind of offensive remarks that cannot be tolerated or excused.” For his part, Rodman indeed seemed remorseful for the outbursts. But he also indicated that he didn't quite realize the remarks had spiritual weight: "If I knew it was a religious-type deal, I never would have said it," Rodman outlined in his apology.

At the height of his fame in 1994, Dennis Rodman had a relationship with the pop superstar Madonna. It was one of the athlete's most highly publicized flings, but they were together for only a few months. Still, Rodman dedicated an entire chapter in his 1996 memoir to their pairing. And he later revealed that she offered him big bucks if he would impregnate her.

"She asked me — if I got her pregnant, she'd pay me $20 million," Rodman told the nationally syndicated radio show "The Breakfast Club" in 2019. "That's if the baby was born," he clarified, saying he was flown last-minute from gambling in Las Vegas direct to New York in an attempt to conceive with her.

Rodman felt that his star power helped raise Madonna's profile at a time when the singer who found worldwide fame in the '80s was, by his estimation, beginning to stagnate. "It's the other way around," Rodman responded when "The Breakfast Club" asked him if the Madonna relationship made him more famous. He explained, "In 1993, I think her career was declining. And she said that the reason why she dated me was because I was a 'bad boy.' But I was going up, and she was leveling off."

It's exciting to think that Dennis Rodman could be a CIA operative. After all, the American former NBA player famously has ties to North Korea. He reportedly first met Kim Jon Un, the leader of the totalitarian dictatorship in the East Asian country, in 2013, and he's since been on several more trips to North Korea. Rodman is something of an ambassador, it would seem, but the results of his many visits to the country still aren't entirely clear.

According to State Department officials, Rodman's reported fifth trip to North Korea in 2017 was purely a personal visit and not in the name of statesmanship. However, his first trip to North Korea was with a "Vice" documentary film crew and three Harlem Globetrotters in tow. The subsequent "Vice" television special about the trip, "Basketball Diplomacy," premiered in June 2013, and simply added to the many bizarre things to originate from North Korea.

But could Rodman's visits to North Korea have actually been done in cooperation with the CIA (Central Intelligence Agency)? Unfortunately, we'll never know for sure, as despite a FOIA (Freedom of Information Act) request submitted by the nonprofit investigative journalism concern MuckRock, the U.S. federal government's civilian foreign intelligence service would "neither confirm nor deny the existence of the requested documents."

Though Dennis Rodman might have surprised some with his endorsement of Donald Trump for president in 2015, those who watched Trump's reality TV series "The Apprentice" knew that Rodman and Trump were already in each other's orbit. In 2009, Rodman was a contestant on Season 9 of "The Apprentice" — then called "The Celebrity Apprentice" for its full docket of celeb players — and he was the fifth contestant fired out of 16 total players. So it wasn't a stretch to guess that Rodman and Trump were already friendly.

Ahead of the 2016 election, Rodman said on X (formerly known as Twitter), "[Donald Trump] has been a great friend for many years. We don't need another politician, we need a businessman like Mr. Trump!" Trump responded on X, saying, "Thank you @DennisRodman. It's time to #MakeAmericaGreatAgain! I hope you are doing well!"

But the real shocker was that Rodman didn't endorse Trump in the 2020 presidential election. In a nearly unintelligible video message Rodman posted on Instagram that October, the former NBA player wears a "Vote Kanye" shirt and appears to endorse Kayne West, the hip-hop star who had announced his bid as a third-party candidate. In the clip, as Rodman unboxes shoes the rapper sent him, he mispronounces Kanye's name several times before being corrected by someone off-camera, the unseen person echoing the charge to "Vote Kanye." Rodman, his rapid speech somewhat difficult to understand, seems to agree.

Notwithstanding what could be theoretically clandestine purposes for his many visits to North Korea, Dennis Rodman does have diplomacy at least somewhat on his mind when dealing with the country's figurehead, Kim Jong Un, and the totalitarian government that rules over one of the world's most secretive societies in the East Asian locale. After all, Rodman has suggested that he's in tune with the North Korean supreme leader.

In June 2018, Rodman attended the widely reported North Korea–United States Singapore Summit between Kim and then-U.S. President Donald Trump, seemingly using his friendship with Trump in an attempt to help smooth tensions between the two countries. Indeed, the former NBA star subsequently said that he thought an agreement between the U.S. and North Korea could actually come to fruition.

"I think that it could still work," Rodman told Reuters of possible peace talks between the U.S. and North Korea. "I just think that we need to stay on the right path to make it work." He added, "So, I think that people should not give up on the U.S. trying to engage with North Korea in a good, safe manner. [...] I think Kim Jong Un wants peace. I know him very well, I think he wants peace. I think people don't realize that he wants to move on into the 21st century. I think he doesn't want to give up his country. I don't blame him."

It's abundantly clear that Dennis Rodman has become more comfortable with himself after so many years in the spotlight. But he was never one to hide his emotions in the name of saving face in the first place. And that includes the 6-foot-7-inch sports star shedding a few tears when the time is right — even if everyone is watching.

In 1990, when Rodman won the NBA's Defensive Player of the Year award, the basketball player got so overwhelmed that tears flowed down his face as his Detroit Pistons teammates consoled him. But Rodman is individualistic to the core, and he has no qualms if people see him cry.

”I don't care what people think of me,” he told The New York Times just days after earning the pro sports accolade. ”It doesn't make you less of a man or more of a man because you cry." Rodman explained, ”A man's going to cry if he does it in public or he's not in public. You feel emotion. I'm not trying to get pity or want people to like me because I cry. I do it because I feel so good inside. It's like when you go to church, and you feel something hit you. The spirit hits you, and it's in a good way. By God, you are going to show emotion.”

Dennis Rodman completed his primary NBA career by playing 12 games for the Dallas Mavericks in 2000, before landing on a couple of American Basketball Association (ABA) teams and subsequently moonlighting on squads in Mexico, Finland, and elsewhere. Even lesser known, however, is that when Rodman was with the Mavericks, he shacked up with famous businessman and "Shark Tank" personality Mark Cuban when Cuban was the Mavs' principal owner, with Rodman staying in Cuban's guest house.

"It's true — he had lost his driver's license," Cuban told "All the Smoke" in 2019. "I have a guest house behind my house. I'm like, 'Just stay there; I can take you' — it was funny. I love D-Rod, right? He would come up to my house, and he would just sit there watching cartoons all day." Impressively, Cuban even said that Rodman taught him much about marketing, and the billionaire entrepreneur praised the athlete for his commitment to making exciting public appearances.

Cuban explained, "I learned more from Dennis Rodman about PR and marketing than I learned in any NBA class [or] anything I've ever done. The man was a master of marketing. [...] We'd go someplace, and there'd be masses of people just excited to see him. He'd be like, 'You just gotta keep refreshing, and coming up with new stuff, and letting people know you're going to be there.'"

Dennis Rodman isn't just a basketball star — he has also participated in the exaggerated world of professional wrestling. For World Championship Wrestling (WCW), he became a member of Hulk Hogan's NWO (New World Order) wrestling group in 1997, making his official debut in the ring at that July's "Bash on the Beach" pay-per-view event in a tag team match with Hogan (then going by Hollywood Hogan) against Lex Lugar and The Giant. However, Rodman had first briefly reared his head in a triangle elimination match with Hogan at WCW's "Uncensored" event earlier that year.

The NBA player only delved further into the pro wrestling sphere from there, even getting one of his fellow basketball stars in on the action: At 1998's "Bash at the Beach," Utah Jazz power forward Karl Malone partnered with Diamond Dallas Page in a tag team match against Rodman and Hogan, truly merging the NBA and the WCW in a way never before done. The match came only weeks after Rodman and Malone had faced each other in the 1998 NBA Finals when Rodman's Bulls defeated the Jazz for their sixth total NBA title.

After his time in the NBA, Rodman continued to dip his toe into pro wrestling, appearing on "Hulk Hogan's Celebrity Championship Wrestling" in 2008. And Rodman continued doing it — as recently as 2023, the now former basketball player appeared on a September episode of AEW wrestling's "AEW Collision" show alongside the AEW wrestling stable The Acclaimed.

In a 2016 installment of Vice TV's "Party Legends," Dennis Rodman shockingly admitted that he had "broke [his] d**k" three different times during sex over the years. The basketball star recalled the final instance as being officially diagnosed with a penile contusion, and also claimed that as many as eight different medical professionals in the emergency room had come over to look at it with bewildered curiosity. After all, Rodman's penis — or any penis, for that matter — "don't bend that way," the former NBA player said one doctor had told him. But for Rodman, at the time, "it don't bend at all," he purported the practitioner also said.

Rodman also had to deal with some unnecessary medical extortion after that last emergency room trip. He said his girlfriend got a call from someone claiming to be with the group of medical personnel, saying they would sell the medical photos that were taken of Rodman's contusion to a tabloid if he didn't pay up. Rodman claimed that his girlfriend said to the person attempting to blackmail him, "Go ahead and do it," and then hung up the phone.

But it's all water under the bridge now, and Rodman can seemingly still engage in sex. "I'm good to go now," he concluded. "I'm good to go, man, it's all good. [I] take a pill. But that's three times I did that — broke my d**k."