When Oprah first became a household name, she got burned by people close to her who sold secrets to the tabloids. One thing that particularly devastated her was in 1990, when the National Enquirer reportedly paid her half-sister $19,000 for the story that Oprah had had a baby boy at age 14, and the child died at birth. Her sister Pat was reportedly furious at the talk show host because Oprah had cut off her $1200-a-month allowance, due to Pat’s alleged use of it to feed a drug habit. Oprah talked years later in O magazine about the betrayal, and how she “took to [her] bed and cried for three days” when the story came out. She also talked about how she was sexually abused during her childhood, and acted out with promiscuity before getting pregnant.
Oprah eventually had everybody who works for her, whether as an Oprah Winfrey Show employee, a vendor, or even people who helped with her dogs, sign a confidentiality agreement. (TMZ found a copy of it.) The document governs what can be said about her — not only while employed by her, but for life. This is why Kitty Kelley’s “tell-all” book about Oprah didn’t reveal much of the story.
For somebody who has made a living talking, it’s a bit strange that the people around Oprah are required to zip their own lips. Especially when in 1998, after she won the lawsuit that Texas cattlemen filed against her, over her comments about beef on the show. At the time, she proclaimed, “Free speech not only lives — it rocks!” But, considering the betrayal she has endured by those close to her, it is understandable why she would crack down on the gossip.