The 64-year-old star has been involved in a high-profile feud with the US president in recent years, and she's now opened up about the origins of their relationship, revealing that she attended Trump's 1993 wedding.
Speaking on the Bleep! with Ana Navarro podcast, O'Donnell said: "I first met him at his wedding to (Maples).
"I was invited because Jason Opsahl, who has since passed away … he was a leading man with Marla in Will Rogers Follies, and then he went to do Grease with me as Kenickie and I was Rizzo. And so he was invited to the wedding. I went as his plus-one.
"And it was like a kick because I thought to myself, 'This is the guy that I grew up watching his planes be repossessed off the runways at LaGuardia, watching him declare bankruptcy all the time, [watching] him arguing with Forbes magazine about that he was richer … but they always said, 'Sorry, we're not putting you on the list because we can't quantify your income.'"
Trump once made a silent, cameo appearance on The Rosie O'Donnell Show, the talk show that ran from 1996 to 2002.
O'Donnell recalled: "I waved from my desk and then I never spoke to him. So, the first time I saw him or was in his presence was at his wedding."
She described Trump, 80, as a "grifter", a "con man", and a "snake oil salesman".
She explained: "If you grew up on Long Island as I did, or in New York City, you knew this your whole life. This was not a surprise."
O'Donnell is also bemused by the idea that Trump is seen as a "moral compass for 20-year-olds in America".
The outspoken star said: "He annoys me on a multitude of levels. He left the first wife, had an affair, left the second wife, had an affair, had kids both times, but he's the moral compass for 20-year-olds in America.
"Donald, sit and spin, my friend. I don't enjoy him."
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