As brilliant a basketball player as Dennis Rodman was, his grip on actual life wasn't as tight as his grip was while grabbing loose balls. From his relationships to his finances to his brushes with the law to his image, he didn't have many things in his life tied down.
Rodman's life was so chaotic that, according to his own agent, Dwight Manley, Michael Jordan wanted to step in, hoping to help steer him onto a more stable path.
Rodman shone as a star for the Detroit Pistons in the 1990s. While Isiah Thomas often took the spotlight, the Pistons' two championships wouldn't have been possible without Rodman's impact, particularly on defense. A two-time Defensive Player of the Year and a five-time All-Defensive First Team selection, Rodman's mastery on the court brought him both fame and fortune.
Unfortunately, he wasn't able to hold onto his money for long due to his legal troubles, which were bleeding his bank account dry. From sexual assault settlements to noise complaints lodged against him for partying deep into the night at his restaurant, Josh Slocum's, Rodman was seemingly handing out money every chance he got.
"Man, all these lawyers are bleeding me. It can't go on much longer, 'cause I ain't got much left," Rodman said in a New York Times piece in 2003. "I've lost almost everything . But the only person I have to blame is Dennis Rodman. That's O.K. by me. Money doesn't mean a lot.''
Picked 27th overall in the 1986 NBA Draft, the first impression that Rodman left on Pistons head coach Chuck Daly was one of shyness. An introvert who did whatever was asked of him, he soon outgrew his timidity and became the bombastic player that fans loved and opponents hated to tangle with.
Sadly, Daly at times didn't agree with the path Rodman chose and the persona he's had to embrace.
"He's lost himself; he can't see where one starts and the other ends. He's convinced he has to play up to that. I know that's not him. The shy kid I met is who he is," he remarked.
One person who shared Daly's sentiments was Manley, who believed that an intervention would help turn Rodman's life around. And he had Jordan's support.
"I've talked to Michael Jordan. He said he'd do anything to help, and I'm trying to reach Chuck Daly," Manley relayed.
Jordan and Rodman had a complicated relationship. They started as rivals — the central figures in the legendary Bulls -Pistons feud — and later became teammates, helping lead the Bulls to their second three-peat from 1996 to 1998.
Friendship, however, didn't come easily.
Jordan admitted that Rodman's signing with the Bulls felt like a slap in the face . He immediately said he had no intention of becoming friends with his new teammates. The two never even talked to each other off the court. But over time, the hatred grew into respect. And based on Manley's words, the respect eventually grew into friendship — of sorts.
Jordan was willing to step in and help Rodman, just as he had offered support to Scottie Pippen with his contract issue . But some things were beyond even Jordan's reach — and Rodman's situation proved one of them.
Rodman did meet with Manley, and the encounter was deeply emotional.
"We went into the back and he told me, 'I'm going to lose everything — please, please help me.' He was crying so hard, the snot was pouring out his nose," Manley recalled.
"I told him to make the first step, to call me, but he never did. He's just a shadow of what he was. It breaks my heart," he added.
Rodman ultimately managed to escape bankruptcy. Despite earning over $27 million in salary alone during his 14-season NBA career, his net worth today is estimated at $500,000. But he continues living life his own wild, unpredictable way — the same fearless spirit that made him a basketball legend.
Related: Dennis Rodman never regretted not shaking hands with Michael Jordan and the Chicago Bulls
This story was originally published by Basketball Network on Apr 10, 2026, where it first appeared in the Old School section. Add Basketball Network as a Preferred Source by clicking here.
