The Most Expensive Gifts Oprah Winfrey Has Given Away

Even if you never sat down to watch an episode of "The Oprah Winfrey Show," odds are you're at least familiar with "Oprah's Favorite Things." Items from the list of Winfrey's favorite items often become gifts given to her fans and friends. Because Winfrey is exceedingly wealthy and an incredibly generous person, she's given away luxurious items, cars, trips, and more, costing her hundreds of thousands of dollars.

Winfrey's generosity isn't news to her fans, as anyone who attended a taping of her show and received a car or something else extravagant knows all too well. Winfrey's been one of the most prominent players in media for more than a few decades, and there are tons of stories about her generosity, leading many to wonder what the most expensive gifts have been over the years.

The list of Winfrey's gifts is long, but not everything she's gifted breaks the bank. One of her favorite gifts is a simple journal, which holds more meaning than it does monetary value. Still, she's never been shy about sharing the wealth, and these are the most expensive gifts Winfrey has given away throughout her long and impressive career.

Oprah Winfrey shows her magazine and Harpo staff a lot of love via cash bonuses, extravagant gifts, and trips around the world, but she's got a lot of employees. Oprah employs numerous people in and around her home, including six housekeepers, and she doesn't forget about them whenever it's time to show her appreciation. Instead of buying them something specific, Winfrey pays for shopping sprees.

According to RadarOnline, Winfrey took her six housekeepers on a Santa Barbara, California shopping spree in 2014. An eyewitness heard the TV host from the front of the store yell out, "Alright, ladies! You have two minutes! Grab whatever you can! Two minutes!" This wasn't a local Walmart, but an expensive boutique stuffed with designer clothes and more.

Winfrey handed the cashier her credit card and explained she would pay for whatever the six women she brought wanted. Winfrey escorted her staff to the shopping spree in a limousine, so the whole affair was more of an elaborate event than a spur-of-the-moment spree. Winfrey has a penchant for gifting people shopping sprees and doled them out on numerous occasions, often as a charitable event to help people in need.

Oprah Winfrey appeared on the cover of Essence's March 2014 issue, wearing an ivory Brian Rennie for Basler feathered dress. The issue celebrates black entertainers' contributions and also features Michael B. Jordan, Forest Whitaker, and Chiwetel Ejiofor. Winfrey looks stunning on the cover, and she impressed user Snobaby Brandi on X, formerly known as Twitter.

Brandi reached out to Winfrey in a since-deleted tweet: "You look beautiful in that Essence cover pic. WOW. CAN I please have that dress? Cuz I know u won't wear again lol luv u" (via Outersparkle). Winfrey agreed, replying, "You're right. I won't wear [it] ever again. Contact my asst. and show her this tweet." One week later, Brandi expressed her gratitude in a since-deleted tweet.

Brandi wrote, "THANK YOU! Recv [sic] beautiful dress. Plan to wear at my wedding when I find a groom lol but will twt pic wearing it soon. Luv u to life!" The value of the dress isn't available, but a custom Brian Rennie for Basler gown goes for several thousand dollars. Add to that the fact that Winfrey wore it on a magazine cover, and the dress is likely priceless.

Oprah Winfrey nearly got married to her longtime partner, Stedman Graham, in 1993, but the couple postponed the wedding indefinitely. They did this because of a coinciding book deal, and Stedman didn't want it to overshadow the wedding. The book and wedding never happened, but the couple remained together despite the lack of nuptials.

While that particular book didn't happen, Graham published several books, some of which became bestsellers. In 2014, Winfrey's stepmother, Barbara Winfrey, spilled the tea on her stepdaughter, telling the Daily Mail all about Oprah's secrets with allegations of unusual behavior in her relationship with Graham and others. What she said is unsubstantiated, but that doesn't necessarily make it untrue.

One of the revelations Barbara made while airing all of her stepdaughter's dirty laundry related to one of Graham's books. According to Barbara, Oprah bought a warehouse and filled it with copies of her partner's books. She did this to ensure the book made it onto the bestseller list, and it evidently worked. The cost of such an exercise is anyone's guess, but the true gift of buying all of those books is getting Graham on the bestseller list, which isn't a gift many can give.

It's well-known that Oprah Winfrey's best friend is fellow TV personality Gayle King. The two became friends in 1976 and remained close ever since. Winfrey once told Barbara Walters (via ABC News), "She is the mother I never had; she is the sister everybody would want; she is the friend everybody deserves; I don't know a better person." That's exceedingly high praise, and Winfrey has repeatedly shown Gayle her love over the years.

While Winfrey has given her friend many gifts, one stands out as the most thoughtful. During an appearance on "Watch What Happens Live" (via Finurah) fans asked King about the many gifts Winfrey had given her. She discussed several, including a heart-shaped diamond pendant, which she considered to be very special to her. Another fan asked, "What is your all-time favorite, favorite thing from Oprah?"

King thought of a moment and said it was a live-in nanny. King gave birth to her second child 11 months after the first was born. Winfrey paid for the nanny to help out, and King explained to host Andy Cohen, "I could never have afforded it." Live-in nannies cost around $1,000 a week or more, but the real gift was the time the nanny afforded Gayle.

Dr. Maya Angelou turned 80 in 2008, and Oprah Winfrey was there to celebrate the event. Winfrey considered Angelou a "mentor-mother-sister-friend" and honored her with a three-day extravaganza held at Mar-a-Lago in Palm Beach, Florida. More than 500 people attended the three-day gala, celebrating the poet's birthday and many accomplishments throughout her life.

Winfrey convinced Donald Trump to close Mar-a-Lago for the duration of the party, ensuring it was an invite-only event closed to the public. Winfrey also arranged for some top-tier entertainment, including Tony Bennett and Donna Summer. Other attendees include Natalie Cole, Tyler Perry, Bryant Gumbel, Quincy Jones, Norman Lear, Andrew Young, Cicely Tyson, and Steve Wynn.

It's unclear how much the event cost Winfrey but renting out the entire Mar-a-Lago property for a weekend can't be cheap. Just the aspect of the gala likely cost several hundred thousand dollars, at the very least. Still, it's not the only party Winfrey threw the poet laureate. Winfrey threw lavish birthday celebrations for Angelou's 65th, 70th, 75th, 80th, and 85th birthdays. These include a party held at the Graylyn Manor in Winston Salem and a Caribbean cruise to see Mayan ruins for 150 people.

Oprah Winfrey has a half-sister named Patricia Lofton, though they didn't meet until 2010. The following year, Winfrey introduced Lofton to the world, and before long, she bought her a new home. Winfrey bought Lofton a house valued at $490,000. A spokeswoman for Winfrey said, "Patricia's greatest dream was to go to college and become a social worker. Oprah wants to support that dream."

The half-sisters share the same mother, but she gave up Lofton while Winfrey lived with her father, never knowing she existed. Lofton left the foster system at the age of seven after her adoption went through, and later in life, she searched for her birth mother. This led to the connection to Winfrey, and a DNA test confirmed their relationship.

Lofton discovered her famous sister after their mother, Vernita Lee, gave an interview disclosing her three children. After putting it all together, Lofton took some time to reach out to Winfrey. In addition to the new house, Winfrey also gave Lofton a monthly stipend so she could quit her job and return to college to become a social worker. She earned a B.A. in Sociology in 2017 from the University of Wisconsin-Milwaukee.

Oprah Winfrey built a media empire over the years, which includes television shows, a network, special events, a magazine, and more. Winfrey's magazine, aptly titled "O, The Oprah Magazine," launched in 2000, and it quickly became a successful periodical that remains incredibly popular and relevant today. When the magazine's tenth anniversary came around, Winfrey didn't forget her staff's contributions.

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." The spokesman didn't elaborate on the number of employees who received the cash and iPad, but surmising the amount is possible.

According to ZoomInfo, "O, The Oprah Magazine" has around 54 employees. Assuming the same was true in 2010, the total amount of cash gifted to Winfrey's employees was $540,000. The report doesn't indicate what kind of iPad Winfrey gave her employees, but the base model cost $499 when it launched in 2010, so the total bonus Winfrey gave her employees was around $567,000.

Oprah Winfrey knows her staff works hard, and she recognizes this often. For her birthday in 2016, Winfrey headed to the Hawaiian island of Maui, but she didn't go alone. Winfrey treated her staff to an all-inclusive vacation. Winfrey didn't just take her executives or other high-level employees; she took 407 employees and their families to stay in the luxurious Grand Wailea Maui resort.

The trip wasn't merely to celebrate Winfrey's birthday. It also marked the 20th anniversary of "The Oprah Winfrey Show," so she threw a Hawaiian-themed party for her staffers and surprised them with the trip. "There are hundreds of people who help me put this show on the air every day. To honor our 20 years in television, I wanted to thank my Harpo family for everything they do — going beyond commitment — to serve our viewers" (via Oprah).

While it's unclear how much the trip cost Winfrey per person, it's not unreasonable to put the figure at around $3,000, though that's a conservative estimate. This is based on the average cost of airfare and hotel accommodations. Since more than 500 people went, Oprah shelled out around $1.5 million for the trip.

Oprah Winfrey created several notable catchphrases over the years, but her best known is probably "You get a car! You get a car! Everybody gets a car!" Oprah surprised her audience in 2004 (via OWN) with a brand-new Pontiac G6 valued at $28,500. Producers hand-picked people for the audience who needed a car, and in the end, "The Oprah Winfrey Show" handed out keys to 276 audience members, costing some $7.8 million.

The show also paid for the sales tax and registration but not the gift tax, which amounted to $7,000. Anyone who couldn't afford it could take and sell the car, or if they wanted, they could refuse it. The car giveaway idea came from Gayle King, and initially, only 25 vehicles were to be given away, but Winfrey kept asking for more until Pontiac sent in 276 cars.

The cost of the cars fell on the car manufacturer, but that doesn't minimize the costs to "The Oprah Winfrey Show." The generous act of kindness was a ratings bonanza for the program, which makes sense since it instilled in viewers the possibility that attending a taping might result in a brand-new car, and they weren't entirely wrong.

Oprah Winfrey's 2004 Pontiac giveaway made her a legend, and in 2010, she outdid herself. Winfrey's producers hand-picked people who needed a car, and once more, she surprised her audience. This time, Winfrey handed out brand new 2012 Volkswagen Beetles, valued at around $19,000. While the car's value was less than the Pontiac, the show threw a cherry on top.

This time around, the show chipped in the costs for everything. Audience members got a new car, and this time, the show covered the costs of sales tax, gross income tax, registration, license, and destination fees. The only things people needed to pay for were gasoline and insurance. Winners also had the option to choose from four colors.

The total cost for the cars was a little over $5.1 million, which VW covered. The Beetle giveaway ranks slightly higher than the Pontiac one due to the added costs the show kicked in to ensure everyone walked away with a new car without the burden of additional fees. It took some time, but 126 VW stores nationwide delivered the vehicles to the lucky recipients within the year.

It seems that one of Oprah Winfrey's favorite gifts is wildly expensive trips for her friends, family, and staff. In 2009, Winfrey paid to take members of her Harpo staff and their families on an all-expenses paid 10-day cruise and European vacation. The trip began with a Mediterranean cruise, taking them to port calls in Malta, Italy, Turkey, Greece, and Spain.

This particular trip wasn't merely to honor her staff — it celebrated Winfrey's 55th birthday! According to the New York Post, Winfrey paid $5,400 per person for transportation, lodging, food, and special activities at the various ports. The total number of people who reportedly went on the cruise with Winfrey was 1,700, which included the Harpo crew and a seemingly massive number of family members.

Given the cost per person, Winfrey spent around $9.18 million for the European vacation. Because of the large number of attendees, Winfrey booked the cruise two years before the Norwegian Gem cruise ship set sail to Malta. Arrangements were made to keep the media away so that everyone could enjoy their trip without the burden of paparazzi trying to snap photos of the staff and their families.

In 2005, Hurricane Katrina wiped out many homes and businesses throughout the Gulf Coast, upending the lives of a million people. People were left with nothing as their homes, cars, and everything else washed away, and Oprah Winfrey was there days later to assess the damage. She made a promise never to forget the displaced families and worked to help as many as possible.

Using her charity, Oprah's Angel Network and Habitat for Humanity, Winfrey helped rebuild the houses for 65 families rehomed in Houston, Texas. The TV host didn't just offer thought and prayers to the families or make a few phone calls — she committed $10 million of her personal funds (via Oprah) to help build the new houses in Texas. Winfrey arranged everything through her charity and teamed up with Houston's mayor, Bill White, to oversee things.

The new homeowners pledged to work with Habitat for Humanity for 300 hours on constructing their homes. They put in the work, ensuring the houses weren't a gift but something they helped create. Houston was only the beginning, as Oprah's Angel Network committed to rehoming 250 families displaced by Hurricane Katrina. The charity raised millions for this endeavor, including a $1.2 million donation from NBA superstar Kevin Garnett.

In 2009, Oprah Winfrey partnered with Kentucky Fried Chicken for a giveaway promotion. It involved a coupon on Winfrey's website, entitling anyone who had it to a free two-piece grilled chicken meal with two sides. This created a problem because anybody in the U.S. could print the coupon and take it to a restaurant, and it was a catastrophe.

Millions of people lined up at KFC restaurants nationwide to receive their free meals, and KFC couldn't keep up. The restaurant issued a statement halting the promotion due to the overwhelming response, though it did offer a rain-check program so people could get their meal at a later date. People downloaded the coupon more than 10.5 million times, and by the time it finished, it cost $42 million (via CNN).

The campaign was a joint venture by Winfrey and KFC, so it's unclear how much of the bill rested on her shoulders. She may not have paid anything, but that hardly mattered because her name was all over the campaign, and as far as anyone cared, Winfrey bought a chicken meal for everyone in the U.S. willing to go out and get it.

Oprah Winfrey spoke with South African President Nelson Mandela in 2000 about the state of education in his country, and two years later, she did something about it. In 2002, Winfrey began a project that developed into the establishment of the Oprah Winfrey Leadership Academy for Girls, a school designed to educate and offer opportunities for impoverished, academically gifted girls.

The school was formally established in January 2007 with an inaugural class of 150 girls, and the student body increased to 450 girls in subsequent years. Winfrey funded the school, costing her $40 million for the construction, furnishing, outfitting, and everything else. She took some flak for adding luxuries that weren't entirely necessary, leading to some claims the money could have been used to educate more children.

Regardless, Winfrey continues to support the school located just outside Johannesburg. OWLAG's website mentions that their mission embraces the concept of leadership, focusing on "the ideals of humanity, compassion, and service to others." The school isn't the only gift Winfrey gave to South African children. In 2004, Winfrey and her crew also distributed 50,000 Christmas presents to impoverished children. The trip helped raise awareness and more than $7 million in contributions.