In fact, Trump knows her so well he named Oprah as his ideal running partner back in 1999 on Larry King Live.
As fans took to social media to encourage Winfrey to consider a bid, CBS News host and close friend Gayle King revealed on Tuesday that Winfrey is "intrigued" by the idea. I do think that the speech was a different moment for her.
What do you think of Oprah Winfrey's press room speech?
"Yeah, I'd beat Oprah", he said. I did one of her last shows ...More news: Dog walks 40 miles to find her former owners
More news: CONCACAF chief responds to Trump 'shithole' slur
More news: Bombshell Claims in the Leaked Testimony on Trump and Russian Federation
"I'll tell ya, she's really a great woman, though".
Years ago Trump talked about Oprah as his potential running mate if he were to ever run, and yesterday he continued to express his admiration for her. Trump boasted that he had been a guest on one of Oprah's final shows.
Paying tribute to Recy Taylor, an African American woman who daringly reported her 1944 gang rape by white men and died last month just short of her 98th birthday, Winfrey deplored "a culture broken by brutally powerful men".
"She loves this country and would like to be of service in some way", King said.
Winfrey was a popular surrogate for President Obama.
Meryl Streep also reiterated her support of the idea, stating: "Whether she is leading us to the candidate we need of whether she herself is a candidate, she sets the bar pretty high on campaign talk".