"I never want to rule it out totally, because I really am exhausted of seeing what's happening with this country, how we're really making other people live like kings, and we're not", he said.
"A lot of people think Oprah belongs in government". "I think one of the arguments against Oprah is 45".
Mr Trump himself has lavished praise on her over the years, including in 2015 when he said he would consider her as a running mate on his Republican ticket.
"Oprah is denying any political ambitions, but two of her close friends told CNN she is "actively thinking" about running for president".
And here's a suggestion she might want to look at...
But after her acceptance speech for the Cecil B. DeMille award - an honorary award for outstanding contributions to entertainment - celebrities and social media users started to rally around the idea of a Winfrey presidential campaign.
She used the show's success to build a media empire encompassing movie production, magazines, cable TV, and satellite radio, becoming one of the world's richest women. I support that as I think everyone should and I think Oprah has a tremendous capacity for human empathy.
If Donald Trump made it clear that a person with high name recognition who sells a coherent narrative to a core demographic can get elected president, irrespective of his total lack of qualifications or relevant experience or knowledge or intelligence, the longing for a charismatic left-liberal celebrity who can reorient America's political compass goes back at least to the Reagan era. "I think we'd win easily, actually", Trump told ABC News at the time.
At the Oval Office meeting on Tuesday, Trump reminded reporters that he had been on one of Winfrey's last shows.
"That said, given the choice between Oprah and our current president, I'm on the bus with Oprah travelling the country encouraging people to sign up and vote", he said. She has a grasp of the issues as she used to cover local politics.
Winfrey brought the typically rowdy crowd to silence and tears with her speech.
In the meantime, as Oprah promised, "a new day is on the horizon" - and it's up to all of us to make sure it dawns.
Peoples reported from NY.