‘That Was a First!’: Here’s the Gift from Bestie Gayle King That Moved Oprah Winfrey

It’s not often Oprah Winfrey seems shocked. Someone actually gave the woman that has everything, something she had never gotten. That person was her best friend Gayle King.

The two were on vacation in Italy in April with a group of other women when the friends decided to go shopping.

Gayle King (left) and Oprah Winfrey (Image: YouTube screenshot, “OG Chronicles”)

When Winfrey went to pay for her items, the cashier told her that her clothes were paid for by King.

Winfrey had footed the bill for the vacay and invited King, King’s daughter, Kirby Bumpus, close friend filmmaker Ava DuVernay, and friend Urania. They took a girls trip to an Italian medical spa, The Palazzo Fiuggi.

King and Winfrey chatted about the trip on King’s web series, “The OG Chronicles.” The series consists of King and Winfrey answering questions from fans and chatting about trending topics. 

‘The OG Chronicles’

In the latest episode of the show, which posted on May 31, the two were asked about the most memorable vacation they have taken together. “This Italy one is top of mine. But we’ve been to some great vacations,” King answered, and added the Winfrey had treated everyone to the international getaway.

That’s when the shopping excursion came up. The group had stopped at one of Winfrey’s favorite stores in Rome.

“So we went on a shopping spree too, and I love a good shopping spree. Nothing better than to be able to shop and fit in the clothes, and y’all know I got new knees so I can fit in the clothes,” Winfrey said, reminiscing on what happened in the episode. “I was going to my favorite store and they had pulled out racks of things and I was [choosing] things, and at the end when I went up to pay the bill, they said Gayle had already paid. That was the first time that ever happened to me!”

Surely Winfrey could have paid for her own clothes, but she seems deeply touched by her friend’s gesture. And King seemed happy to be able to treat one of the world’s richest women.

“That was a first! I was so happy to be able to do that because I’ve never been able to do that before,” King said in response.

Lasting Friendship

Winfrey and King have been friends for more than 40 years, having met in 1976 when King was a 21-year-old production assistant at WJZ-TV in Baltimore, where Winfrey was a news anchor. 

The two women quickly bonded.

Over the years, Winfrey and King have supported each other through thick and thin. They have been there for each other through divorce, personal tragedies, and career highs and lows.

Winfrey’s net worth is estimated at $2.5 billion, making her the richest Black person of the 20th century, according to MarketWatch.

She is also the richest self-made woman in America and the fourth-richest Black person in the world behind venture capitalist Robert Smith, Nigerian billionaire businessman Mike Adenuga, and Nigerian businessman and industrialist Aliko Dangote.

King has an estimated net worth of $30 million. She is best known for her work as co-anchor of the CBS morning news program, “CBS This Morning,” and will soon be hosting a once-a-week program on CNN with Charles Barkley, “King Charles.” King will reportedly earn $12 million for the gig.

With her mega CNN deal, there might be more shopping sprees in the near future.

 “I’ve done a lot of shopping sprees for other people but no one’s ever done that for me,” said Winfrey, and added jokingly, “But now, you know Gayle, she’s on CBS and CNN.”

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