8 Most Expensive Gifts Oprah Winfrey Has Given to Friends, Family and Her Staff

8 Most Expensive Gifts Oprah Winfrey Has Given to Friends, Family and Her Staff
Cover Image Source : Getty Images | Photo by Rachel Luna

Oprah is known for her generosity of spirit, but here are 8 times she outdid herself!

Image Source: Jon Kopaloff | Getty Images
Image Source: Getty Images | Jon Kopaloff 


Oprah Winfrey has been one of the most well-known figures in the media for several decades, and because of all the tales about her generosity, many people are curious about the most costly presents she has given over the years. Fans of Winfrey are well aware of her generosity; just ask anybody who was there at a recording of her program and wasn't left with an expensive car or anything else. She has, nevertheless, occasionally surpassed even herself. Here are eight examples of when she not only did something heartwarming but hit it out of the park with how costly it was.

1. Oprah built a school for South African girls in 2002

Image Source: Getty Images | Raymond Hall
Image Source: Getty Images | Photo by Raymond Hall


Oprah is not one to sit silently after knowing about a problem. In 2000, shortly after discussing the situation of education in South Africa with President Nelson Mandela, she took action two years later, per Nicki Swift. Winfrey started an initiative in 2002 that eventually led to the creation of the Oprah Winfrey Leadership Academy for Girls, a school whose mission is to educate and provide opportunities for academically brilliant but disadvantaged girls. The school was fully funded by Winfrey, who spent $40 million on its design, construction, equipment, and general furnishings. Winfrey is still a supporter of the institution, which is situated not far from Johannesburg. According to their mission statement on their website, OWLAG upholds the idea of leadership by emphasizing "the ideals of humanity, compassion, and service to others."

2. Oprah's famous car giveaways

Image Source: Getty Images | Matt Winkelmeyer
Image Source: Getty Images | Photo by Matt Winkelmeyer


Over the years, Oprah Winfrey came up with several memorable catchphrases, but nothing comes close to "You get a car! You get a car! Everybody gets a car!" In 2004, the producers of The Oprah Winfrey Show hand-selected audience members in need of a car, and the end, The Oprah Winfrey Show gave 276 audience members keys to a brand-new Pontiac G6, which was valued at $28,500 and cost approximately $7.8 million. 2010 saw her surpass herself. Hand-selected by her producers, Winfrey stunned her audience once more by choosing folks in need of a car. This time, Winfrey gave some audience members brand-new 2012 Volkswagen Beetles. It came to slightly more than $5.1 million in all.

3. Oprah took her staff and their families on a luxurious Europe trip

Image Source: Getty Images | Arturo Holmes
Image Source: Getty Images | Photo by Arturo Holmes


In 2009, Winfrey covered the costs of a 10-day cruise and European holiday for her Harpo employees and their families. They started their journey with a Mediterranean cruise that stopped at ports in Malta, Italy, Greece, Turkey, and Spain. For transportation, Winfrey spent $5,400 per passenger, or around $9.18 million. To ensure that everyone could enjoy their holiday without worrying about the paparazzi wanting to take pictures of the personnel and their families, arrangements were devised to keep the media at bay.

4. Oprah rehomed hundreds after Hurricane Katrina

Image Source: Getty Images | Emma McIntyre
Image Source: Getty Images | Photo by Emma McIntyre


Days after Hurricane Katrina claimed hundreds of lives in 2005, Oprah Winfrey visited the area to evaluate the damage. Oprah Winfrey assisted in rebuilding the homes of sixty-five families who were relocated to Houston, Texas, by using her charity, Oprah's Angel Network and Habitat for Humanity. The TV host donated $10 million of her own money to support the construction of the new homes in Texas. Oprah's Angel Network promised to find new homes for 250 families that were uprooted by Hurricane Katrina, so Houston was just the beginning. The NBA player Kevin Garnett donated $1.2 million to the charity, which helped raise millions of dollars for this project.

5. Oprah gave her half-sister a London house worth $490K

Image Source: Getty Images | Steve Jennings
Image Source: Getty Images | Photo by Steve Jennings


Although the two did not meet until 2010, Oprah Winfrey has a half-sister named Patricia Lofton. Winfrey presented Lofton to the public the next year, and soon after, she purchased a new house for her. Winfrey paid $490,000 for Lofton's home. "Patricia's greatest dream was to go to college and become a social worker," a Winfrey spokesman stated. "Oprah wants to support that dream."

6. Oprah gave her magazine staff an iPad and $10K each

Image Source: Getty Images | Jason Koerner
Image Source: Getty Images | Photo by Jason Koerner

Upon celebrating the tenth anniversary of Oprah's publication O, The Oprah publication, Winfrey didn't overlook the contributions made by her crew. A magazine spokesman told Reuters, "As a thank you for their hard work and dedication, Oprah Winfrey surprised the staff of "O, The Oprah Magazine" with an Apple iPad and a check for $10,000 to commemorate the magazine's 10th anniversary."

7. Oprah bought a warehouse full of her partner's books

Image Source: Getty Images | Tommaso Boddi
Image Source: Getty Images | Photo by Tommaso Boddi


In 1993, Oprah Winfrey and her longtime lover Stedman Graham almost tied the knot, but they decided to put off their nuptials forever. Due to a concurrent book contract, they took this action because Stedman didn't want it to dominate the wedding. The book and marriage never took place, but the couple didn't part ways. Instead, they stayed together. Once, Oprah purchased a warehouse and stocked it with her partner's book titles. She took this action to make sure the book reached the bestseller list, and it seems to have been successful.

8. Oprah gifted a live-in nanny to Her Best Friend Gayle King

Image Source : Getty Images | Rachel Luna
Image Source: Getty Images | Photo by Rachel Luna


Winfrey paid for the nanny to help out when King gave birth to her second baby, only 11 months after the first one. King related the incident on Watch What Happens Live, telling host Andy Cohen, "I could never have afforded it." Live-in nannies can cost up to $1,000 per week, but Gayle's time with the nanny was the true gift.

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