"I know her very well. That would be a painful experience for her".
But he harkened back to when he and his family were interviewed during the final weeks of "The Oprah Winfrey Show" in 2011.
Winfrey, however, didn't let Trump's insults get the best of her.
"We had you, we had the Obamas in the White House, so even on a bad day, you had a north star - you had some hope", said Jones. "Wouldn't we love to run against Oprah?"
But in recent months he's called on Winfrey to run - just because he thinks he can beat her.
"My grandfather took in people from the Freedom Riders in MS and risked his whole family and home", Winfrey said on the show, referring to civil rights activists who were attacked while trying to desegregate public bus transportation in 1961.