When Oprah Winfrey endorsed Barack Obama in 2008, it was a big deal. Today, the Democratic Party is trying to turn Kamala Harris into Obama 2.0, and naturally, the party thought it was a good idea to un-retire Oprah the billionaire from irrelevancy to give a speech at the Democratic National Convention and gush about the most unpopular vice president in history.

Naturally, Trump had an epic response to Oprah's DNC speech endorsing Harris. He shared a handwritten letter to him from Oprah, dated Jan. 11, 2000.

Donald, I received the book excerpt. I have to tell you, your comments made me a little weepy. It's one thing to say and live a life of integrity—still another to have people like yourself notice.

Thank you,

Oprah

Too bad we're not running for office. What a team!

Oprah's letter to President Trump: pic.twitter.com/QY1kYifPJS

— Trump War Room (@TrumpWarRoom) August 22, 2024

Years before that letter, in 1988, Donald Trump was also on her famous talk show, during which she suggested that he run for president.

"You took out a full-page ad in, major U.S. newspapers, last year criticizing U.S. foreign policy. What would you do differently, Donald?" Oprah asked him during the show.

Trump responded by expressing his frustration over the U.S. being a "debtor nation" and how we were unfairly treated by its allies. He specifically cited Japan for benefiting from American markets without reciprocating, calling it "not free trade" since selling American products in Japan was nearly impossible. 

He also pointed out that countries like Kuwait, which benefit from U.S. military protection and oil sales, should be paying more for the privileges they enjoy. He suggested that allies need to pay their fair share, as the U.S. couldn't sustain its economic losses indefinitely.

Related: CNN Contributor Drops Major Truth Bomb About the DNC's Messaging

"This sounds like political presidential talk to me, and I know people have talked to you about whether or not you wanna run. Would you would you ever?" Oprah asked.

"Probably not," he said. "But I do get tired of seeing the country rip off."

"Why would you not?" she asked.

"I just don't think I really have the inclination to do it," he replied. "I love what I'm doing. I really like it."

Oprah later pointed out Trump had said previously that if he did run for president, he believed he would win.

"Well, I don't know. I think I'd win," he said. "I tell you what. I wouldn't go in to lose. I've never gone in to lose in my life."

FLASHBACK: President Trump on Oprah’s show in 1988 talking about countries ripping America off in trade.

She even suggested that he may run for president some day. 👀
pic.twitter.com/iWiCWeOzO2

— Trump War Room (@TrumpWarRoom) August 22, 2024

And the receipts keep coming. Oprah even promoted JD Vance's memoir, "Hillbilly Elegy," in her book club.

Boosted by Oprah’s Book Club, among other notables, Vance suddenly became a sought-after Trump translator on talk shows in the fashion of “Luther,” President Barack Obama’s fictitious “anger translator” created by the “Key & Peele” comedy team.

Not surprisingly, Hollywood wanted a piece of this action. Popular filmmaker [Ron Howard] brought cast and crew to Middletown — including stars Amy Adams as Vance’s drug-addicted mother and Glenn Close, his memorably profane but tough-minded grandma.