Oprah Winfrey's Tragic Real-Life Story

Oprah Winfrey, the Golden Globe lifetime achievement award-winning talk show host and media mogul, has built a billion-dollar empire, which ultimately landed her at the No. 1 spot on Forbes' 2017 list of America's richest female entertainers. A celebrity who seems to have it all — including oodles of cash at her disposal; a stable, long-term relationship with her partner, Stedman Graham; and a best friend, Gayle King, who never leaves her side — surely had an idyllic childhood as well, right?

Sadly, that's not the case. However, Winfrey was born with the gift of gab, and she always dishes out a dose of genuine compassion to everyone she comes in contact with. In her 2019 book, The Path Made Clear: Discovering Your Life's Direction and Purpose, Winfrey has advice for everyone who faces tragedies and challenges in life. "This is the lesson I hope you take away," Winfrey wrote (per CNBC). "Your life is not static. Every decision, every setback, or triumph is an opportunity to identify the seeds of truth that make you the wondrous human being that you are."

Inspiring words from an inspiring woman. But behind her gentle smile and kind heart lies a harrowing tale. This is Oprah Winfrey's tragic life story.

Oprah Winfrey's early years were chock-full of instability. It all began in rural Mississippi, where Winfrey lived with her maternal grandmother, Hattie Mae Lee. She was then shipped off to Wisconsin to live with her mom, Vernita Lee, when she was 6 years old. This move turned out to be the most dramatic of them all. "I suddenly land in a place that's completely foreign to me. I don't know anybody. I don't really even know my mother," Winfrey told HuffPost in 2015. "I walked into that space feeling completely alone and abandoned."

Before the future media mogul could get settled in Wisconsin, she was sent to live with her dad — or, rather, a man she presumed to be her dad — a coal miner named Vernon Lee, in Tennessee, before eventually returning to live with her mom once again. The constant changes in her surroundings definitely took a toll on her, but Winfrey told the publication that it was her faith that helped her push through. 

"I grew up with an understanding that there was this God — all-knowing, all-powerful — who loved me," Winfrey said. "The wonder of that, the magical mystery of that, is what carried me when I was separated from my grandmother and sent to live with my mother at 6 years old."

Born to teenage parents who conceived her after a one-time fling, Oprah Winfrey's early years were spent on her grandmother's aforementioned rural Mississippi pig farm, according to the New York Post, and life was less than ideal. 

She and her grandmother didn't have much money, so their home was lacking common amenities. Running water and electricity were scarce. However, Winfrey reportedly enjoyed the wide open spaces that were available, as it was in direct contrast to the tiny apartment she shared with her mother and two half-siblings, Patricia and Jeffrey.

As with most incidents in her early life, abuse sadly crept its way back into the forefront. This time, it was physical. "I went to a well to get some water and carry it in a bucket. And I was playing in the water with my fingers, and my grandmother had seen me out the window and she didn't like it," Winfrey once told David Letterman in 2018 (via News.com.au). "She whipped me so badly that I had welts on my back and the welts would bleed. And then when I put on my Sunday dress, I was bleeding from the welts. And then she was very upset with me because I got blood on the dress ... So then I got another whipping for getting blood on the dress."

These days, Oprah Winfrey has an entire team of stylists who get her all dolled up in gorgeous, red carpet-ready gowns, and her work closet at Harpo Studios in Chicago is filled to the brim with designers duds. But this self-made multi-billionaire didn't always have a collection of pricey, luxury goods to choose from. Growing up in extreme poverty, Winfrey had no choice but to wear hessian overalls made out of potato sacks. Her untraditional, makeshift outfits caused her to be crowned with the heartless nickname of "Sack Girl," according to The Guardian.

When describing her childhood on the farm, Winfrey told David Letterman (via News.com.au), "I grew up in an environment where children were seen and not heard." This household ethos caused her to retreat and look for engagement in other places. The Guardian reported that, instead of having the typical farm animals as her pets, Winfrey had pet cockroaches instead. And since her family couldn't afford a box filled with toys for her, she made her own babydoll from a dried corncob.

During the time she lived with her mom, Oprah Winfrey experienced intense colorism — a term used to describe intra-group prejudice that favors lighter skin.

Recalling the time she arrived at the home where her mother was renting a room, Winfrey told HuffPost, "I remember the first night entering into that house and being told that I wouldn't be able to sleep with my mother and I wouldn't be able to sleep inside the house." She said, "There was a little foyer/porch before you actually got inside the house. I was put outside to sleep there."

Winfrey was confused at first, but she later realized exactly what was going on. "My mother was boarding with this very light-skinned black woman who could have passed for white ... I could tell instantly when I walked in the room that she didn't like me. It was because of the color of my skin," the talk show queen explained. Instead of putting up a fight, the young Winfrey obliged and found solace within her sleeping arrangements, looking toward her faith for comfort. "I remember praying on my knees the very first night I had been removed from my grandmother," she said. "I don't remember ever shedding a tear about it because I knew that God was my father, Jesus was my brother, and they were with me." 

Oprah Winfrey's usually in the driver's seat when it comes to grilling her guests and getting to the bottom of important issues on The Oprah Winfrey Show and her later endeavors. However, the tables were turned when the talk show maven sat down for an interview with David Letterman and his Distinguished Professional Lecture and Workshop Series (via the Daily Mail). It was at this time that she opened up about her traumatic childhood, including the brutal rape she survived when she was just 9 years old.

Winfrey peeled back the layers of that experience even further in an issue of O, The Oprah Magazine. "I was living in Milwaukee that summer, staying at an uncle's home, when a 19-year-old cousin raped me. As I trembled and cried, he took me for ice cream and convinced me not to tell — and for 12 years, I didn't," she wrote. It wasn't the last time she would be violated as a child. Winfrey had told Letterman that she was also molested by various relatives when she was between the ages of 10 and 14.

After being sexually abused numerous times during her formative years, Oprah Winfrey's self-esteem and self-worth were beyond crushed. The Oprah Winfrey Network CEO later wrote an emotional piece for her publication, O, The Oprah Magazine, and explained, "It was a very long time before I understood how completely my life had been changed — how in one instant, I was no longer a child." She continued, "When you are sexually violated, it's not the physical act that destroys you. It's the weight of the secret you feel you have to keep, the person you have to become so no one will discover what you're hiding."

The traumatic experiences caused Winfrey to confuse "mistreatment with love." And it took her many years to come to grips with the entire ordeal, as she went on to add that she held the belief that she "had done something to cause the abuse" up until her 30s.

While chatting with CNN's Piers Morgan in January 2011, Oprah Winfrey revealed that, after getting pregnant at 14 years old, she tried to drink laundry detergent in an attempt to terminate the pregnancy (via New York Daily News). At the time, the future actress and talk show host tried to make sense of the turn her life had taken at an early age.

"Getting pregnant was a result of bad choices, not having boundaries, sexual abuse from the time I was 9, 10, 11, 12 and 13," Winfrey said, before explaining that she began doing "crazy stuff that you do when you're trying to get attention, when you're really just trying to cry for help."

Tragically, Winfrey would later lose her child shortly after giving birth (more on this below). A loss, of course, is often accompanied by some form of grief, but looking back on the way everything played out, Winfrey was able to find the silver lining. She later told Good Housekeeping UK, "I didn't want babies. I wouldn't have been a good [mom] for babies. I don't have the patience." She then quipped, "I have the patience for puppies, but that's a quick stage!"

In 2017, Oprah Winfrey told The Hollywood Reporter that, after she got pregnant at 14, she "hit rock-bottom." But things were far worse than anyone could've imagined. 

We've previously mentioned Winfrey's attempt to terminate her pregnancy by drinking laundry detergent, but that was only one part of her plan. "I became pregnant and hid the pregnancy. I'd intended to kill myself actually," she said in a heartbreaking statement. "I thought there's no way other than killing myself. I was just planning on how to do it. If I'd had the Internet, I might not be alive because now you can just Google how to do it."

Winfrey went on to explain that the reason for wanting to harm herself came after she was sent to live with her father in Nashville. At the time, he had no idea she was pregnant when she moved in, and he reportedly made the following heartless comment (via the New York Daily News): "I would rather see a daughter of mine floating down the Cumberland River than to bring shame on this family and the indecency of an illegitimate child."

If you or someone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline at 1-800-273-TALK (8255) or text HOME to the Crisis Text Line at 741741.

According to People magazine, Oprah Winfrey welcomed a son when she was 14 years old. But sadly, he was born prematurely and died in the hospital shortly afterwards. Additionally, when the teen worked up the courage to tell her family about the possibility of her favorite uncle being the father of her child, they brushed off her allegations. "Because I had been involved in sexual promiscuity," Winfrey told the media outlet, "they thought if anything happened, it had to be my fault."

Looking back on her early pregnancy, Winfrey told the New York Daily News that she had "no connection" to the baby whatsoever. So, in her eyes, losing the child was a blessing in disguise. "When the baby died, I knew that it was my second chance," she said about getting a new lease on life. Despite feeling detached, an Australian news reporter encouraged her to give her deceased son a name, and Winfrey obliged by telling a crowd at an event, "So I have named him, I had a little boy named Canaan ... And I named him Canaan because Canaan means new land, new life." 

Oprah Winfrey is an open book when it comes to sharing tidbits of personal information about her life, but the startling admission that she experimented with drugs was something she never intended to talk about. The media mogul had been filming a program about drug addicts who were in recovery back in January 1995 (via The Washington Post). After one woman shared her story of smoking crack cocaine, Winfrey reportedly said she also went through a period of drug use with an ex-boyfriend.

She later decided to dive a little bit deeper into the topic in an interview with the Today show. However, she admitted, "I had used drugs in my 20s with this boyfriend and I was more addicted to the boyfriend than I was to the drugs." When former Today show host Billy Bush asked if her drug of choice was crack, Winfrey answered, "Yeah, well it wasn't called crack at the time. It was called freebasing. It was before crack was crack."

As she soared to fame and became known as one of the most prominent television figures, some of Oprah Winfrey's less-than-loyal kin attempted to cash in on her celebrity clout. One family member in particular, a now-deceased half-sister, was the one who spilled the news about Winfrey's teenage pregnancy in exchange for a $19,000 payout, the New York Post reported.

And, years later, it was Winfrey's own dad who attempted to make an easy buck by penning a tell-all book about his daughter. Once the talk show host found out about his plans, she told the New York Daily News in 2007 that she was "shocked" and "disappointed," especially since she had just seen him a few months prior and he didn't even let on that he had a book in the works. "The last person in the world to be doing a book about me is Vernon Winfrey," she told the publication. 

With family members like these, who needs enemies?

On Thanksgiving Day of 2018, Oprah Winfrey lost her mother, Vernita Lee. She was 83. TMZ was the first outlet to report the sad news, which a spokesperson for Winfrey later confirmed (via HuffPost): "The family of Vernita Lee are saddened to share of her passing ... at her home in Milwaukee, Wisconsin."

Despite Winfrey's rocky relationship with her mother early in her life, the two eventually reconciled. Less than a month after Lee's death, Winfrey opened up to People about spending time with her mother during her last days in hospice care. "I sat with my mother. I said, 'I don't know if you're going to make it. Do you think you're going to make it?' She said, 'I don't think I am,'" Winfrey explained. "I had a conversation with her about what that felt like, what it felt like to be near the end. I started telling all the people who cared about her that, 'She knows it's the end, so, if you want to say goodbye, you should come and say goodbye.'"

After everyone traveled to say their "sacred and beautiful" goodbyes, Winfrey did the same. "I stood in the doorway and I said, 'goodbye,'" she told the outlet. "I knew it was going to be the last time we said goodbye." Winfrey added that one of the last things she told her mother before she passed was, "'Thank you. Thank you, because I know it's been hard for you.'"