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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.

With her closed cropped, red-haired curls, Jenny once won a Little Orphan Annie look-alike contest.

Jenny, our mom and me in a Brady Bunch moment.

Jenny was a pint-sized tennis phenom. I loved my wooden Chrissy Evert racquet. After we posed for this picture, I’m pretty sure the little punk soundly beat me on the public tennis court across the street from our house.

Here we are rocking the knee socks.

Jenny, featured here with family friend Kirsten Cline-Schubbe, in her Little League days. Don’t let Jenny’s smile fool you, she could throw a mean right hook.

It looks like Grandpa Fey (a Vince Lombardi look-alike here) is offering Jenny a few tips about her game during this college tennis match but I think they’re actually conferring on where to get a post-match piece of pie. While he loyally followed her tennis career all over the Midwest, my Grandpa didn’t know a thing about the game.

This is Jenny and Charlie at her college graduation. Today, she is a co-executive producer for Oprah’s Next Chapter and he is an associate producer for Anderson Cooper.

Here’s a recent photo of me, my sister Kathy and my sister Jenny. Kathy is a Wisconsin State Teacher of the Year, Jenny is an Emmy winning producer. I … write about them.

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Posted on July 2, 2012, in Jenna Kostelnik, Jenny Kostelnik, kostelnik, Oprah, Oprah producer, oprah winfrey show, Oprah's Next Chapter. Bookmark the permalink. 15 Comments.

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