Winfrey receiving the Presidential Medal of Freedom from President Obama in November of 2013. Photo by Evan Vucci/AP

“The truth is I try not to let other people define for me whether I have power or don’t,” Oprah Winfrey has said.  “I ended [my talk] show and then there were a whole bunch of people who said, ‘Oh, you don’t have power anymore.’  But the truth is I know who I am and the thing about power for me is that it’s connected to a source that’s obviously greater than myself. Any time you can connect to the source and understand that that’s where all of your energy and your creativity, your joy and your triumph come from, I consider that authentic power.”

Authenticity is the key to Winfrey’s rise to power from her humble childhood in Kosciusko, Mississippi, where she was raised by her grandmother Hattie Mae who taught her to read before Winfrey was three-years-old and where there is now an Oprah Winfrey Boys & Girls Club, which she established a few years before her Oprah Winfrey Leadership Academy for Girls in South Africa.  Through her time as a news anchor in Tennessee and Maryland – where her roommate was lifelong friend Maria Shriver – to her big break as a local morning talk show host in Chicago before going national, Oprah Winfrey’s most winning attribute has been her incongruously regal realness.  Unlike her weight, it has never fluctuated.  Indeed, even the fluctuations in her weight enamored her to her audience and made her one of them in spite of all the wealth she was accumulating.  It was a balancing act that called upon more than a graceful bearing which, thanks to Hattie Mae no doubt, Winfrey has always had in abundance.   It also needed the sure-footedness of someone who doesn’t like wearing heels.

Such sure-footedness was tested when, after ending her talk show, she created OWN, the television network which struggled to gain its own footing in the changing media landscape.  Winfrey lost her way a bit as she focused more on content at OWN than intent. Conceptualizing intent and then manifesting it has always been her talent as a teacher and conduit instead of a mogul, which itself is too mundane a monicker to describe her place in the country’s consciousness.  Winfrey’s stumble at the beginning of OWN was the first time since being fired from her anchor job in Maryland that she had ever experienced any sort of perceived setback in her charmed public life.  She had, among a myriad other triumphs, already had success syndicating other talk shows for Dr. Oz and Dr. Phil, creating a magazine for Hearst, bringing in needed profits for publishing houses with her book club selections, being nominated for an Oscar for The Color Purple, winning a Tony for  producing the musical version of it, and even helping elect the country’s first African American president with her endorsement of him.

Stepping into the national discourse in such a way was something Winfrey had always shied away from since she has always realized her audience is a diverse one politically.  In that, she preceded President Obama himself in the need, as the two most famous and respected African Americans,  to cultivate a precisely calibrated presence – by turns down-home and dignified – as they each threaded a cultural needle they still thread with their nonthreatening tenacity so as not to offend those who would be too readily offended, without even acknowledging it, by the momentous yet unsettling success of these two they profess to admire.  Black people have always attained fame in America but becoming a billionaire businesswoman and the country’s first black president disrupted norms in rather radical ways even as these two disrupters of the mainstream continue to distance themselves from any notion of radicalism itself.   Each a child of disruption in the most personal sense, they have not only sought a sense of safety in their rise to power but also in a more abiding and lasting way to be a source of safety themselves for others.

Service has been the driving force in each of their lives; power has been its byproduct.  Obama was a community organizer and Winfrey in her many media enterprises and platforms organizes her Oprah community in ways she hopes will better lives.  A recent business gambit was to be the spokesperson for Weight Watchers which conflated for her in many areas – her own aforementioned battle with weight (she lost over 40 pounds going on its program), her desire always to lead others toward their better selves, and her heralded business acumen.  She was not only the spokesperson for the company but also sits on its board and is its third largest shareholder with 6.4 million shares of the company — a stake now worth over $150 million which is a small percentage of her $2.9 billion fortune.   But talking about Winfrey’s worth in dollar amounts misses the whole point of how those dollar amounts got to be so impressive.  Oprah Winfrey’s mission was not to make a fortune but to own her life.  The fact that  OWN is the acronym for her network is one of those heightened coincidences that can only be explained by that source greater than herself  having a sense of humor, as Winfrey certainly does about herself. 

With Winfrey at a picnic in Los Angeles.

I once ran into her at a picnic thrown by a gracious married couple, both cultural machers themselves, on the grounds of their Beverly Hills home over Oscar weekend in Los Angeles and Winfrey has kindly allowed me, based on my own discernment, to share a bit of our visit that day.   The  picnic was the kind of sun-dappled afternoon affair where Sheryl Sandberg and Jeff Bezos watched movie stars mingle and Rupert Murdoch lined up for mac’n’cheese.  I had earlier sent Winfrey, at her request, my last memoir, I Left It on the Mountain, to read.  The book focused on my drug addiction and subsequent sobriety and I had hopes of being on her Super Soul Sunday show on OWN to talk about it.   We had discussed that it might be a possibility for me to do so.   I had, alas, never heard back from her but thought I might  run into her there at that picnic.  When I did, she walked right up to me, put her hands on my shoulders, and squared me in her sights.  “I didn’t like your book,” she bluntly told me.  “It was so loud.  I loved your first book, Mississippi Sissy.   But this one … I don’t know … I just didn’t respond to it and I didn’t think my audience would either.  I always have to think about the trust my audience has in me.  I wasn’t sure how this served that trust.”

I had already deduced that Winfrey hadn’t liked the memoir – it was a pretty rough road through drug addiction to get to the chapters about my own spiritual redemption – but it still was disappointing.  I bucked myself up though.  “You know,  I always said when that book was published that if it helped one person to find his or her way to sobriety  then it was worth writing it,” I told her.   “I met a young guy recently at one of my meetings back in New York who told me that the reason he was there was because he had read that book.  So I had to own what I had claimed.  I wish I’d been on your show, Oprah, but helping that one person meant the book had found its audience.”

Winfrey smiled.  “When the film of Beloved came out, I had such high hopes for it but it really wasn’t the hit I had hoped it would be.  I was despondent about it.   Gary Zukav was talking to me about it – and my despondency,” she said, mentioning the author and spiritual teacher whose book Seat of the Soul has served as an ur-text for Winfrey’s guileless, unerring, continuous journey toward enlightenment.  “He said that the film of Beloved had touched him deeply and that if the film could touch one person in the way that it had touched him then that was enough.  It had been worth doing it.    I thought about that.  Really thought about it.  And I decided, no, that’s not enough.  I want to touch more than one person.  So you’re a better person than I am, Kevin,” she joked.

As we laughed, I realized that was the basis of so much of Oprah Winfrey’s appeal.  For all her heartfelt New Age philosophizing, for all her hard-earned billions, for all her historical cultural pioneering, there is this: Oprah Winfrey does not bullshit.  It’s as simple as that.  And brilliant.  In a world where – sadly and maddeningly – deception and deceit increasingly pay and can move a decimal point a few zeroes over in the right direction when measuring monetary worth, which is itself a skewed measurement of self-worth,  it is even brave.  Oprah Winfrey speaks truth to power: herself.  Her source of power is the empowerment of others.  There is greatness in that. 

She’s got a nice laugh, too.

  • Kevin Sessums is the author of two New York Times bestselling memoirs, Mississippi Sissy and I Left It on the Mountain.

  • Show Comments

  • Ric Harrison

    I really enjoyed the story and totally believe that it is Oprah’s no bullshit that keeps her so authentic. I struggle with being authentic, sometimes i just have t0 bullshit them. But hey, I’m not dead yet.

  • Candice Blackman

    Sometimes I get upset that people hold Oprah with such reverence….you, Kevin, made me see her in a different way. I get it now, and like her MORE ❗️

Your email address will not be published. Required fields are marked *

comment *

  • name *

  • email *

  • website *