Oprah and the Oval Office

Headline NY Daily News October 1999 Donald Trump Wants Oprah For His Vice President in Presidential run

Long before Julia Louis Dreyfus served as Americas favorite Vice President, another TV celebrity with mega watt star power was seriously considered for the second banana spot. Well sort of, if you consider the top banana spot was to be filled by a megalomaniac best known for bankrupting casinos.

Today  that mega watt star Oprah Winfey’s name is  being bandied about not as Veep but as POTUS to run against that same megalomaniac, President  Donald Trump.


The thunderous applause at the Golden Globes had not even quieted before twitter erupted in a cacophony of tweets imploring Oprah to run for president in 2020. After her rousing speech accepting the Cecil B. DeMill Award  #Oprah4Potus began trending on twitter.

A gushing Meryl Streep told the Washington Post “She launched a rocket tonight. I want her to run for President.”

The prospect of these two titans of TV, Winfrey vs Trump clashing for the coveted title of President of the United States in 2020 seems irresistible and tailor-made for social media.


Ironically, our current Reality TV President seriously once considered the Queen of Talk as his potential running mate when the real estate mogul eyed a run for president in 1999.

Our political landscape has changed as dramatically as our culture has since the end of the Twentieth Century.

At that time we were still buying CD’s at Tower Records, that is when we weren’t waiting hours to download one song off of Napster and praying you wouldn’t be knocked off the internet while it downloaded. Not only did we carry both a beeper and a cell phone, we checked our email maybe every few days because we were so busy driving from Blockbuster to Blockbuster in search of a new release we wanted.

Oh, and we read actual books primarily because Oprah recommended them.

Some things from that year sound eerily familiar – the national tragedy of a mass school shooting at Columbine, talk of Presidential impeachment and speculation about Vladimir Putin. The last year of the century began with President Clinton’s acquittal in impeachment proceedings  and ended with Boris Yeltsin resigning as President of Russia elevating Prime Minister Vladimir Putin to acting President.


In 1999  The Donald had yet to reach his reality TV level of fame which was a good 5 years off into the future. Oprah on the other hand was a major TV star, a force to be reckoned with and  far richer than the N.Y. builder could ever hope for.

Their paths had crossed many times including interviews on her show,  and when Trump toyed with the idea of running for President on the Reform Party ticket he wanted Oprah as his running mate.

Trump told anyone who would listen his choice was Oprah. “I think,” he told TV host Larry King “we would be a very formidable choice. I love Oprah. Oprah would always be my first choice.”

Oprah and Trump a Media Match Made in Heaven?

The America We Deserve Book by Donald Trump

Written by Donald Trump and author Dave Shiflett the book was published in January 2000 while Trump was considering running for president in that year’s election on the Reform Party Ticket

Foreshadowing his MAGA campaign in 2016, he released a book called “The America We Deserve,” not unsurprisingly a stream of consciousness whirlwind of free association, self-aggrandizement, and pseudo policy proposals that shift and be bop around erratically from one side of the ideological spectrum to the other.

In the book he wax’s poet about Oprah.

Trump goes on to cheer Oprah as “a literary kingmaker and queenmaker” who catapults “authors featured by her book club” to “the bestseller list.” These qualities, Trump wrote, are what make Oprah his ideal running mate.

“In early October I announced formation of a committee to explore a run for the presidency. At the time I announced that my first choice for vice president would be Oprah Winfrey,” he wrote. “If I can’t get Oprah,” Trump added. “I’d like someone like her.”

At the time, representatives from Winfrey’s camp politely declined Trump’s offer.

The Winfrey speculation was rampant enough that the media weighed in.

“We’ve no doubt Ms. Winfrey could offer many fine traits as vice president—chief among them the athletic ability to wrest Mr. Trump’s hand away from The Button—yet, we like to think the office requires slightly different skills from those of talk-show host,” argued an op-ed in the Newark Star-Ledger.

At the time, the idea of a TV Talk show host as vice president of the United States seemed as ludicrous and laughable as well,  that of a Reality TV star being President.

No one is laughing now.

The Hunger Games

The adoration and appetite for celebrity and the total disregard for experience that has become our new norm in the age of Trump, has brought us to this  place in history now.

It has been a recipe for disaster.

American politics and American governance is more than “uplifting” moments no matter how inspiring they are. With all due respect to Oprah, our hunger for her Presidential run points more to how severely undernourished we are for  real, substantive leadership.

Lets use our 20 20 hindsight in 2020.

Copyright (©) 2018 Sally Edelstein




  1. American politics and American governance is more than “uplifting” moments no matter how inspiring they are. With all due respect to Oprah, our hunger for her Presidential run points more to how severely undernourished we are for real, substantive leadership.

    Lets use our 20 20 hindsight in 2020.

    Hear hear Sally! I was dumbfounded when America put another silver-screen actor into our highest office in 1981 — the biggest disaster from that administration was a Wall Street and Corporate America unfettered, running wild, greedy, and corrupt thru Deregulation Galore — and he lead us into the first round of insanity called the “Savings & Loan Crisis 1989!” And we still didn’t learn our lesson.

    Yes, let’s stop all the disastrous HYPES getting into our key offices in Washington D.C.

    With all that said, Oprah absolutely spoke to a LOT of people’s hearts, to change, and to SPEAK YOUR TRUTH women!!! Don’t stop speaking it! My eyes were welling up listening to her. She is a phenomenal woman/spokesperson for great causes… hands down. ❤

    Liked by 1 person

    • My heart swelled and I got goosebumps listening to Oprah’s electric speech at the Golden Globes and spoke of in yesterdays post. That said, let’s let Oprah be Oprah and allow a seasoned politician to govern us and develop policy

      Liked by 1 person

      • Yes! If I wanted to restore/rebuild a 1940 Supermarine Mk III Spitfire with a Rolls-Royce Merlin XX supercharged engine, I would NOT hire Tom Hardy, from the film Dunkirk who portrayed Farrier, one of the Spitfire pilots in the movie! But hey, that’s just me. Apparently many Americans are HAPPY to put an actor in the pilot’s seat of their airplane! Go figure. 😨

        Yes, Oprah is an “expert” in HER particular field. She would make a fantastic spokeswoman for a campaign/cause, no doubt.

        Liked by 1 person

      • Stevon Brock

        Who wants to be governed Sally,,we are free to choose,,


  2. Stevon Brock

    Oprah would be a disaster as Prez,and all this hype about women speak your truth what truth,all liberals seem to think women has no rights,crazy,Woman Power,Give me a break,,


  3. When I first read of this, I failed to whack my head against the wall only because I didn’t think of it.

    We need to get over this need to yell ‘So-and-so 2020!’ every time some celebrity says something remotely profound.

    No billionaires running because they think it would be fun to be President.

    No celebrities running because we STILL think amateurs should be in the highest office. If they want to be in politics, let them start local, or at least Congress.

    Vote for someone who knows the names and where the bodies are buried (so to speak) and can get things done.


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