How Oprah Winfrey Spends Her Billions

Oprah Winfrey is known as the queen of the talk show world, and she has an estimated $3.5 billion net worth to show for it. Her extreme success is even more admirable because she is self-made, and she's the only Black female billionaire in the United States, per Forbes. "The Oprah Winfrey Show" was an undeniable hit for the 25 years it was on the air. Winfrey went on to launch her cable television network OWN in 2011, and she even tried her hand at acting, starring in the award-winning 1985 film "The Color Purple" (which earned her Oscar and Golden Globe nominations), and "A Wrinkle in Time" in 2018. Winfrey told Wellesley College graduates in 1997, "Turn your wounds into wisdom," and nothing could be truer for the famous host. 

The OWN founder was born in rural Mississippi, according to the Academy of Achievement. She had a rocky childhood and was a victim of child sexual abuse. Oprah moved from her grandmother's home to her mother's in Milwaukee before being homeless at just 14 years old. Finally, she stayed with her father in Nashville, Tennessee. "As strict as he was, he had some concerns about me making the best of my life, and would not accept anything less than what he thought was my best," Oprah said. A beauty contest win granted Oprah her first job with an African American radio station. At 19 years old, she was Nashville's first female Black news anchor

While she enjoys the fruits of her works, this star is also philanthropic. We're breaking down how Oprah Winfrey spends her money.

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A sprawling Maui estate

What better way to bask in the glory of being Oprah Winfrey than doing so in the Hawaiian sunshine? According to AD, the famous talk show host purchased two properties on Maui in 2003 at about $5.3 million, giving her over 163 acres of lush green landscape. Per her website, the media mogul bought her ranch-style home after her personal trainer found available property on the island, which was his favorite vacation spot. Concerned that the land might get snatched up to develop condos, he convinced Winfrey to buy in the remote, countryside region of the island facing the sea. Winfrey also owns her own private road, one that connects two towns on Maui, and one that could ease a lot of traffic if the public was able to access it, according to MauiTime

But Winfrey's charming Maui ranch home is just one of her many luxurious properties. The media mogul owns a 23,000-square-foot-mansion in Montecito nicknamed the "Promised Land." It's part of a much larger compound that the Daily Mail estimates is now nearly 80 acres and worth $90 million due to expansions over the years. Winfrey even sold Jennifer Aniston her next-door farmhouse in 2022. Per the Los Angeles Times, Oprah's main manse was not on the market in 2001 when she bought it, but the star made an irresistible offer of an estimated $50 million. 

Winfrey also owns a state-of-the-art Telluride mansion next to the ski lifts, and she formerly held property in Washington State on Orcas Island

Oprah is incredibly philanthropic

No matter how much success Oprah Winfrey has achieved, the OWN founder always gives back in major ways. Winfrey was the first-ever honoree of the Academy of Television Arts and Science's Bob Hope Humanitarian Award. In 2011, she received the Jean Hersholt Humanitarian Award. She's a crusader for human rights, and she champions the Oprah Winfrey Charitable Foundation (OWCF), which serves underprivileged communities, families, and youth. 

Oprah loves to give toward education, and she heavily increased her scholarship endowment at Morehouse, a historically Black college in Atlanta, in 2019. Her previous donation reportedly paid for nearly 600 students to attend the university over three decades (per NBC News). "I was really surprised to learn that it's been 30 years since I made that $12 million donation to Morehouse, and so today, I would like to add $13 million to that," Winfrey said at the time.

Winfrey made a big impact when she donated $12 million in COVID-19 relief funds in 2020. The OWCF gave grants to five areas the media mogul once called home, which included Nashville, Milwaukee, Baltimore, Chicago, and her hometown of Kosciusko, Mississippi. Winfrey told The Associated Press, "Look in your own neighborhood, in your own backyard to see how you can serve and where your service is most essential. That is the real essential work, I think, for people of means." She added, "What this pandemic has done is made me think about giving differently. How I give and who's on the receiving end of that, and how do you do that in such a way that sustains people?"

Her private plane

Oprah Winfrey's billionaire fortune affords her certain advantages, like having her own private jet. Winfrey revealed to British Vogue that her "greatest luxury" is owning the airplane, which she was driven to purchase after a less-than-pleasant interaction at an airport. "A woman came up and she said, 'You're not acting like you do on TV.'" The star remembers this being the moment when she'd had enough airport inconveniences. Winfrey explained to The Hollywood Reporter that she immediately called up her lawyer and told him, "I'm going to get the plane. This is going to be my last time waiting four hours in the Chicago O'Hare Airport." 

Winfrey had a hard time justifying the $25 million dollar check she wrote for her G4. Her former pal Bill Cosby attempted to soften the blow by telling her that no justification existed for the "true luxury" of owning her own wings. Eventually, the OWN founder came to terms with her purchase. "I remember I had seen Camille Cosby at Teterboro when I was chartering a plane," Winfrey told The Hollywood Reporter, "... So I get on Mrs. Cosby's plane and Mrs. Cosby is on the plane with a pair of overalls and diamond stud earrings and she's on her way somewhere to work on her doctorate and I said, 'Where is everybody?' And she said, 'There's only me.' I said, 'You're going to use this whole plane?' And she said, 'I'm worth it.' Just like that. And I went, 'Well, if she's worth it, maybe I'm worth it.'

Jet-setting with her bestie

It's a good thing that Oprah Winfrey has a private jet, because the media giant loves to travel. Her best friend of 46 years and fellow television personality Gayle King is Winfrey's plus-one most of the time, and they've certainly gone the distance in their past travels together. In 2006, they opted for a less lavish excursion and took a 10-day cross-country road trip together in a Chevrolet, traveling from Santa Barbara all the way to New York City. The journey was documented on Oprah's website to commemorate "The Oprah Show's" 20th season. 

Her inspiration was a car commercial jingle that sang "See the U.S.A. in a Chevrolet" when Winfrey was growing up. "It was 30 seconds that really stuck with me for several decades," the host said. Her trip went off without a hitch, other than Winfrey learning how to pump her own gas for the first time in years: "I thought maybe they'd changed the pumps since I last pumped." Billionaire problems, anyone? 

The dynamic duo knows how to have a good time, and they even jet-setted to Ibiza to party alongside The Black Eyed Peas' and Disney CEO Bob Iger in 2015. Gayle King posted an Instagram snap of their Spanish island vacation, where Winfrey showed off her work-hard-play-hard lifestyle. "They say it's better in Ibiza!" King wrote, adding, "@oprah leads @jimmyiovine in tequila shots! Good times good friends." Winfrey's even been truffle hunting in the Italian region of Umbria, where she posted an Instagram among her fellow hunters, noting that this was a bucket list item.

She has sponsored vacations with her staff

Oprah Winfrey has a big heart, and if you're lucky enough to work for the media mogul, she might even fly you to Hawaii. She did just that in 2016 when her staff members took a trip to her second home on the picturesque island of Maui. The Emmy winner posted a Facebook pic of the occasion with the caption, "Dreaming with the dream team in Maui." The group, which must have exceeded 50 by the looks of her post, celebrated Winfrey's birthday with a sunrise hike on the majestic Valley Isle. 

It's not just Hawaiian vacations that have us filled with boss envy; the talk show host also sponsored a Mediterranean cruise for her lucky staff members in 2009. According to the Daily Mail, Winfrey paid over $600,000 for the 10-day getaway, which stopped in Turkey, Spain, Italy, Greece, and Malta. "The cruise is a gift from Ms. Winfrey to her staff for their sacrifices..." an Oprah spokesperson supposedly told the New York Post at the time. The OWN founder was reportedly nice enough to allow her employees' families to tag along for the lavish, all-expense-paid trip.

Oprah's Weight Watchers investment

If you're an Oprah Winfrey fan, you've probably seen the famous "I love bread" ad that the talk show host did for Weight Watchers. That same ad, launched with a single tweet by the television personality, earned her $12 million dollars, according to MarketWatch. While most of us can only imagine a reality where we make millions by tweeting about bread, Oprah lives it. "I believe in the @weightwatchers program so much I decided to invest, join the Board, and partner in #wwfamily evolution," Winfrey tweeted in 2015.

Winfrey turned Weight Watchers into a major success, buying a 10% share in the company for over $43 million in 2015, per USA Today. Those dollars equated to a $400 million dollar investment by 2018, according to CNN Business. That year, thee company's stock increased by 70%, and it was trading at $75 a share, up from $7 a share when Winfrey came on board. But in typical Oprah fashion, she gave her charitable foundation 361,000 shares, and they reportedly sold them for $22.6 million. 

Winfrey frequently advertises her Weight Watchers lifestyle on her Instagram, even giving her fans some encouragement over the holidays. At the start of 2022, she posted an IG video throwing away her best friend Gayle King's birthday cake. "We ate every day, like food had just been invented," she said. 

She bought her own television network

On the heels of the award-winning "Oprah Winfrey Show," she decided to get her feet wet by giving her brand its own channel. OWN (named after Winfrey), debuted in 2011 and was the first cable network dedicated entirely to a person's brand. At the time, Winfrey said the decision to start the network was terrifying. "I have never felt such fear in all my life...I was afraid of failing...I was afraid it wouldn't be what 'The Oprah Winfrey Show' has been, and has meant, for all these years," she shared in "O" magazine (via Reuters). 

She launched OWN with Discovery (who contributed $100 million) in an equal partnership, per Forbes. The business venture got off to a rough start, however, and initially reported losses. With the world of streaming introduced and cable networks struggling to compete, it's no surprise that the television mogul sold off most of her shares in her own company. 

According to Bloomberg (via Business Standard), she sold more than $36 million in stock to Discovery, which has a 95% stake in OWN at the time of this writing. The network focuses on lifestyle and entertainment programming for Black women and African Americans, according to Winfrey's website. The visionary has spoken out on the importance of representation on-screen for people of color. With the launch of Discovery+ in early 2021, Winfrey also entered an exclusive content streaming deal there. 

She's an investor in True Food Kitchen

Oprah Winfrey expanded her investment portfolio by adding True Food Kitchen restaurant to her list of equities. The restaurant chain announced in 2018 that the famous talk show queen made a notable investment in the company, keeping in line with her passion for health and wellness, as per Eater. True Food Kitchen is a health food restaurant franchise that boasts an anti-inflammatory approach along with sustainability and organic ingredients.

In addition to having a stake in the company, Winfrey also has a spot on the board of directors. With the help of her investment, the health-based chain was able to expand into cities like New York, New Jersey, and Jacksonville. "It's not only a partnership from a financial point of view, but it's also a partnership where she as a great business woman will be lending her thoughts on the market and how we evolve," said True Food Kitchen CEO Christine Barone. The venture appears to be ongoing, as a Miami location opened in summer 2022.

Her luxury cars and classic rides

Oprah Winfrey doesn't just give away cars, she drives them, too — luxury ones, of course. In 2015, she added a Tesla to her collection, captioning an Instagram post, "Test driving my new Tesla with dealer Dan. Love it!!" Winfrey has been vocal about how much she cares for the environment, writing on her website, "I love land. Aside from my own body, it's the physical thing I value most." The Tesla purchase is in line with her values, given that the eco-friendly car runs on electricity. There's no telling what other luxury vehicles this woman owns.

The television personality reportedly has an eye for classic cars, and she once owned a 1954 Mercedes-Benz 300 SL Gullwing, a 1988 Rolls-Royce Corniche II Convertible, and a 1997 Aston Martin DB7 Volante, according to Sports Car Digest. All three of the classic cars were sold at auction to benefit the Oprah Winfrey Leadership Academy for Girls.

She made a huge donation to the Smithsonian

Oprah Winfrey paid it forward in a major way when she made the largest donation in history to the Smithsonian's National Museum of African American History and Culture. In 2013, the philanthropist donated $12 million to the museum, up from her $1 million dollar investment in 2007. Winfrey has been a member of the Smithsonian's advisory council since 2004, and in appreciation for her donation, a theater in the museum was named in her honor. "I am so proud of African American history and its contributions to our nation as a whole," Winfrey shared in a statement, per The Washington Post. "I am deeply appreciative of those who paved the path for me and all who follow in their footsteps. By investing in this museum, I want to help ensure that we both honor and preserve our culture and history, so that the stories of who we are will live on for generations to come."

The media mogul made the large gift three years before the museum opened, a testament to her belief in the project and unwavering support. Founding director for the museum, Lonnie G. Bunch, told the newspaper, "Every donation, whether $25 or a $10 million corporate donation, is important. But truly, there's only one Oprah Winfrey." The National Museum of African American History and Culture debuted in 2016, and it is the only national museum dedicated solely to documenting "African American life, history, and culture," according to its website.

Oprah Winfrey owns a school in South Africa

Oprah Winfrey advocates strongly for education — so much so that she decided to open her own academy. The idea originated in 2002 from a meeting with the late former South African President Nelson Mandela. After they shared their beliefs in education as a tool to conquer poverty, Winfrey shared her desire to open a girls' school in South Africa, and Mandela vowed to put her dreams in motion. 

In 2007, the philanthropist founded the Oprah Winfrey Leadership Academy for Girls (OWLAG). Winfrey spent more than $40 million to build the facility, per her website. The school boasts a 52-acre campus, state-of-the-art classrooms and computers, and a 10,000-volume library for those lucky enough to study on the grounds. OWLAG only accepts one percent of the 6,000 girls that apply annually, and 90% of the school's graduates go to college, including renowned universities such as Oxford, Stanford, and Spelman. 

Winfrey frequently funnels funds into the school, putting her own proceeds from auctions toward her academy. In 2015, the media mogul auctioned off her designer clothing, furniture, paintings, and other possessions from her Chicago home to benefit OWLAG, the AP reported. Winfrey has a long list of life accomplishments, but OWLAG is closest to her heart. "This school is my greatest legacy," she said, per the Oprah Winfrey Charitable Foundation