The Ah Ha childhood of an Oprah Winfrey producer

With a lion’s head of hair and equally impressive roar, the baby of our family intimidated us all. We called my sister “Boomer” and often saw her stand toe-to-toe with our father, a physically imposing man. He had trouble punishing her, though, because she always made him laugh.

Undersized throughout her childhood, Jenny delighted in a good battle. I once saw her leap out of the house and sprint half a block to confront a junior high friend who had copied the outfit Jenny had selected to wear that day. Abashed, the young girl went home and changed.

A state-ranked though selectively competitive athlete, Jenny once rounded third base, heard an insult hurled at her from the opposing player, stop short midway to home plate, doubled back and threw a punch. Both players ended up ejected from that Little League game.

Little did we, her mellower siblings, know that Jenny’s feistiness and cheerful disregard for convention would lead her into a fascinating career.

For the past 16 years, Jenny has worked for Oprah Winfrey. She began as a production assistant (ironically tipped off to the job opening by her co-worker and recreational softball teammate back in 1996). Today she works as a co-executive producer for Oprah’s Next Chapter.

In her years with the Oprah Winfrey Show, Jenny has met countless celebrities and world leaders, and has travelled to exotic places. One March several years ago she called me, giddy, to announce that she was heading to the Bahamas for a show on Sexy Island Men. Exactly one year later, she found herself driving through frozen Canada in search of David, the boy who was raised as a girl. Such is the capricious nature of the television industry. Her work on the “Inside the Taliban” show landed her a lifetime spot on government watch lists and, to this day, she is consistently pulled from airport security lines. For a time,  she fielded emails from the Ayatollah’s office.

For many years she produced the annual Favorite Things show, a carnival of elaborate creativity. Two years ago, I stood in my living room with goose bumps on my arms and watched her successfully launch Oprah’s 24th season with an iconic flash mob featuring the Black Eyed Peas and 29,000 people. Last season Oprah launched the popular “Behind the Scenes” reality show and gave us all a glimpse of our little sister in her work environment, a view we found both impressive and hilarious.

Jeff Probst wrote a column recently about how to produce a television talk show.

The producer he describes? My little sister, Boomer.