My visit with Oprah, Part One

In 1986, my assistant transferred a call to me from a press agent wanting to arrange a meeting with the Governor I worked for.  His client, he informed me, was a Chicago broadcaster who was poised to become “the next big thing” on the national talk show circuit.

As the Governor’s press secretary, I was used to fielding such requests. But this one had an urgency and quality about it that I paid more attention to than usual.

“Can you please pronounce her name again?” I asked, trying to spell and make sense of a name I’d never heard of before.  Orpa? Opha?

“It’s Oprah Winfrey. Oprah is a name from the Bible,” he patiently explained.

I granted the up-and-coming talk show host a 15-minute “meet-and-greet” session with the Governor.  She would be in town to promote the national launch of her show.

And, then I had to tell the Governor about the broadcaster he would be meeting with.

“What’s her name?” he asked, after I’d already told him. “Just call her Ms. Winfrey,” I suggested.

When the day arrived, I stood at the Governor’s office entrance waiting for the press agent and his client to arrive.  They came on a golf cart and out charged the biggest ball of energy I’ve ever met.

She was wearing yellow stretch pants, a sweatshirt and sandals. Her hair was big and flowing but small compared to her personality.  For three seconds, I worried whether I’d made the right decision in granting her time with the state’s high-ranking official.

While we waited for the Governor, she was talkative and fun and asked a hundred questions.  We gossiped about people in Chicago we knew in common.  I loved that she seemed to know about the love life of Chicago’s mayor as well as details about the movie star who was getting divorced.

Her energy and intensity were unlike any person I’d ever encountered.

I wish I could remember what was said during the 15 minutes between her and the Governor but I have no recollection at all.  What I do remember is this: when I signaled the end to the session, Ms. Winfrey rose from her chair, reached over, pinched the Governor’s cheek, and announced, “oh, you’re a cute one!”

I nearly fainted and worried that I would be in big trouble for setting up the meeting. I wasn’t! The Governor was a good sport and thought nothing of it.

She stayed a few minutes to chat, wondering how I thought the meeting went (“oh, great,” I said, biting my nails) and then off she went.  Bemused, I watched her leave and I thought, “wow, no grass is going to grow under that woman’s feet.”

Since then, I have met up with Oprah several times, but I had not been with her in a decade until last week when I went to Harpo to watch two tapings for OWN’s Life Class with Dr. Brene Brown. (More on that tomorrow!)

In Oprah’s office living room, with Dr. Brene
Brown and Brene’s twin sisters

Afterward, I was invited to her private quarters at Harpo and she graciously spent time with a small group of us.  She’d changed her clothes after the taping and came out in sandals and the same color of yellow blouse as were her stretch pants 27 years ago!

Side-by-side with Oprah last week after
first meeting 27 years ago!

I reminded her of that summer she traveled the country to promote her new show and met with the Governor.  She remembered by saying simply, “that’s what we had to do back then.”

In her company today, the atmosphere was relaxed and celebratory.  There was Champagne flowing and a roaring fire in her office fireplace.  She bounced from person to person chatting and laughing before coming to rest on the edge of her sofa.


Talk turned to her new movie Lee Daniels’ The Butler and she marveled at “the absolute glory” of Forest Whitaker’s acting and what he is able to do without even saying a word.

I told her my favorite part of the movie was (SPOILER ALERT!) when she was dying.  To my utter delight, in that moment, Oprah transformed into Gloria in her final scene and perfectly repeated the dialogue where she looks at her granddaughter’s photo.  It was an amazing moment!

What struck me is how in the 27 years that have passed, she has become a billionaire and one of the most powerful women on the planet – and she’s hardly changed at all!

She’s authentically herself – social, noisy, opinionated and full of questions, wearing sandals and her beautiful hair big.  Other than nicer quality clothes and make-up, she remains as always — a big ball of AMAZING energy!

Tomorrow: My visit with Oprah, Part Two — Dr. Brene Brown shares the power of vulnerability