Amid widespread calls that Oprah should run for presidency in 2020, an extract from Donald Trump's book has resurfaced, detailing how much the businessman-turned-politician wanted to have her work with him at the White House.
Friends said private discussions had been ongoing for months, adding that she was "actively thinking" about running for President.
After two days of heightened speculation, Mr Trump said he did not think she would end up running but thought he could defeat her if she did. She was just walking home from the church service she'd attended in Abbeville, Alabama, when she was abducted by six armed white men, raped, and left blindfolded by the side of the road coming home from church. And she was the one person who could do it so strongly.
Holding court in the VIP row of tables up front, Winfrey sat with Gayle King and Wrinkle in Time director Ava DuVernay, their seats turned toward the stage, where word of the internet campaign reached her.
"We welcome the challenge, whether it be Oprah Winfrey or anybody else", said Mr Hogan Gidley.
After college, she went into journalism before reigning for 25 years as queen of the U.S. talk show, ushering in an era of confessional television before becoming the first black woman to own a television network.
Oprah also branched out into acting. She was cast as Sofia Johnson in the Steven Spielberg-directed film, which saw her nominated for a best supporting actress Oscar in 1986.
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"I also know, after years of watching the Oprah show, you always have the right to change your mind". Yes it is. May we all greet it with hope, resolve and faith.
"I do think she's intrigued by the idea, I do think that", King said on the CBS This Morning program.
"She's certainly a bigger celebrity than Trump ever was, especially in terms of connecting with her audience".
Singer and producer Brad Walsh wrote: "She is quite literally the Antitrump".
On an evening when women at the awards show wore black in solidarity with those who have suffered sexual harassment , Winfrey, 63, said: "She (Ms Taylor) lived as we all have lived - too many years in a culture broken by brutally powerful men".
Weight Watchers, which was hammered by free fitness apps and years of subscriber losses, has mounted a comeback since Winfrey bought a stake, joined the board and agreed to pitch the brand in 2015.