"A year ago, I would've agreed", he said, throwing a subtle jab to President Trump.
Saying the "law of averages" will see all entrepreneurs fail at some point, Winfrey advocates getting beyond disappointment and into determination. "I think Oprah would be great". But it was her support of women calling out sexual harassment that fueled talk among Democrats in states where presidential runs usually begin, Iowa and New Hampshire. "Their time is up".
Following her rousing and poignant speech at the 75th Golden Globes on Sunday night, a number of celebrities and luminaries called for Oprah to launch a campaign for 2020.
But if politics is a money person's game, then the odds are still long.
Some of Winfrey's confidants have been privately urging her to run, the sources said. Her exalted name is often hurled into the bonfire of wishful politics.
However, the new poll suggests 48 per cent of likely USA voters would opt for Ms Winfrey if she did enter the fray, compared to 38 per cent who said they would vote for Mr Trump. This idea gained traction after Winfrey's partner, Stedman Graham, was quizzed about the possibility of a presidential bid and promptly contradicted all of her past denials.
"It is the insatiable dedication to uncovering the absolute truth that keeps us from turning a blind eye to corruption and to injustice, to tyrants and victims and secrets and lies", she said. Winfrey's denial of any plan to seek office. But in a post-Trump political landscape, that traditional path may not matter. The dieting company's shares jumped 12.2% in trading Monday to close at $52.62, up $5.71. That's a drop in the bucket for her net worth, which Forbes has estimated at $2.8 billion.
But some would argue the similarities end there.
Mr Trump said this week he did not think Ms Winfrey would run for the White House, noting that he knew her "very well" and had appeared on one of the final episodes of The Oprah Winfrey Show.
"I want all the girls watching here and now to know that a new day is on the horizon", Winfrey said.
Might that foster a better relationship with the press than the Trump or Obama administrations? Being president isn't like hosting a talk show or running a media brand.
"All this stuff about what people usually do is out the window", he said.
"Oprah has read books, she knows how to identify talent. Oprah Winfrey just fired a warning flare in the sky for anyone who still doesn't get that the parties no longer control their own nominations".
So far, Rep. John Delaney of Maryland is the only Democratic politician to have declared his candidacy for president in 2020, and it's unclear what other big-name politicians may enter the race.
Some responded on Twitter with photos of Winfrey with film producer Harvey Weinstein, who has been accused of raping and sexually assaulting multiple women.
"Oprah. I love Oprah. Politically there's a lot of tough terrain for her to scale before she can be realistically thought of as a candidate for president".
But look, I get it. Democrats have been traumatized by recent events, and one of the responses is to throw up your hands and say, "Fine then".
"In 2011, I told some jokes about our current president at the White House Correspondents Dinner, jokes about how he was unqualified to be president".
And in a 1999 interview with Larry King, he said she would be "always be my first choice" for a running mate.
"She's certainly a bigger celebrity than Trump ever was, especially in terms of connecting with her audience".
She won a lifetime achievement award and delivered an impassioned speech about women's empowerment. "It would be a pretty good ticket".