In 2019, Dennis Rodman claimed on 105.1's The Breakfast Club that Madonna once offered him $20 million to impregnate her. While Mr. Rodman isn't known for being a shining example of honesty, it wasn't his first time making those claims.
In a 1995 ESPN interview with Roy Firestone, before he joined the Bulls, Rodman confirmed that he had a thing with the pop music icon.
Firestone: "I just wanna know, how well do you know Madonna?"
Rodman: "I didn't know her that well. I mean I knew her but we talked a lot and that was about it."
Firestone: "Did you have a fling?"
Rodman: "I mean, you know, we had a fling. We had a fling."
Firestone: What do you think she understood or had a better understanding of that most people don't?
Rodman: Probably nothing. She'd probably slap me for saying this right now. She's an individual that we got along real well and it's still the same right now, we're friends, and that's it."
It sounds almost contradictory that he would claim he doesn't know her "that well" that while also saying they used to have a fling. Either he uses the word "fling" loosely or he knows her way better than he was letting on.
Either way, it seems that they have some history together. Whether or not the real truth of the said relationship has been completely expressed is something we'll probably never know for sure, but it sounds like Rodman's business anyway.