Bill Clinton was on Air Force One when he heard that one of his party's most precious donors called his marriage and ran off with Anna Wintour.
The then US President picked up the phone and called Shelby Bryan's long-suffering wife to express his deepest condolences.
That 1999 gesture highlighted the importance of Wintour's wealthy Texan lover and family to Clinton, not to mention their status in US public and political life.
When the dust settled on their scandalous business, Vogue editor-in-chief Wintour and telecommunications tycoon and entrepreneur Bryan became one of America's most powerful couples, a match that was seemingly made in heaven when it came to the worlds of fashion and business to connect and politics.
But now, 21 years after their passionate love affair made headlines on both sides of the Atlantic, it looks like it is all over.
In February of this year, Wintour reportedly "shone" and "looked happier than ever" when she was pictured with actor Bill Nighy. Pictured: the couple in January of this year
The news was published yesterday in New York, where the 70-year-old British magazine Supremo has been considered the most influential woman in fashion for more than three decades.
Given how much she and Bryan sacrificed to be together, it's not surprising that speculation about the cause of their split is rife.
There's also a question mark about whether the couple was ever actually married, and a well-placed source indicates that they never tied the knot and that the relationship has been over for some time.
According to multiple reports in the US media, the couple's romance began to cool back in 2013 when 74-year-old Bryan owed the IRS – the American equivalent of Inland Revenue – £ 1.2 million in unpaid taxes.
For some time there have been rumors and denials that Bryan could return to his former wife Katherine, whose future husband, the investment banker Damon Mezzacappa, died in 2015.
A source close to Katherine Bryan reportedly insisted the two simply remained friends because of their children.
Tongues also wag of Wintour's friendship with actor Bill Nighy – the two have been seen together at fashion shows, theaters and restaurants in New York and London since 2010.
In January of this year, Wintour is said to have been "radiant" and looked "happier than ever" when she and Nighy were seen eating together in New York – so happy that she even took off her sunglasses for a moment.
70-year-old Nighy has always refused to comment on whether their friendship is actually love.
Rumors have been circulating about Anna Wintour and Bill Nighy since 2015 when the two were spotted together at fashion shows, theaters and restaurants in London and New York City
When asked about it in 2015, he replied: “Of course I have nothing to say about it. There are a lot of rumors about me and probably about Anna Wintour. "
It has certainly been a while since Wintour – who has two grown children, Charles  and Bee  with her first husband, the South African child psychiatrist Dr. David Shaffer – Seen with Bryan.
One of the last times they were photographed together as a couple was at the US Open tennis championships in 2018.
On that occasion, the grumpy-looking couple barely appeared to be able to look at each other, and one photo shows Wintour leaning away from him – their body language is frosty.
The picture was a stark contrast to previous years, when Wintour was openly affectionate to Bryan.
The powerful couple began their romance in 1999, which caused a stir among New York’s elite after Bryan reportedly left his wife to be with Wintour. Pictured: Wintour and Bryan at the New York Children's Fall Gala in New York, 2002
Another shot that was taken again at the US Open 11 years earlier in 2007, for example, shows her with arms lovingly wrapped around him, her cheek resting on his hair.
In the early, heady days of their romance, the two are said to have been unable to keep their hands off each other.
Shortly after their relationship became public, the couple were spotted attending a party for his brother at the exclusive Bayou Club in Bryan's hometown of Houston.
There they are said to have behaved "like a couple of constant youths at a bottle spin party".
According to an observer, front row quoted in the 2005 Wintour Biography, "Shelby and Anna spent much of their group throating each other and sitting on a bench in a small foyer . "
Another compared the couple, both in their fifties, to a "young couple in love" and said they were the first on the dance floor: "They kissed and he was all over her."
Anna Wintour was spotted in New York for the first time since splitting up with Shelby Bryan on Thursday
The fashion guru was seen without rings when she stepped out in New York this week
The chemistry between the two was evident from the moment they met in November 1997 when they were seated next to each other during a New York ballet gala – both were married to other people.
At the time, Bryan was considered the Democratic Party's rainmaker after raising $ 1.5 million for candidates like Al Gore from fundraising drives at his Upper East Side home. He was also a member of the Clinton Foreign Intelligence Advisory Board.
He and Wintour were certainly more than a match for each other. The unabashedly ambitious Wintour was previously referred to as the "godmother" of the fashion mafia, while Bryan was described in a 1999 article in New York Magazine as "a conspicuous extrovert with undisguised social ambitions".
Their meeting came at a time when Wintour was showing an increasing interest in politics.
In December 1998 she had "the extraordinary Hillary Clinton" on the front page of Vogue at the start of the presidential impeachment in Congress.
A source speaking at the time her affair with Bryan went public said that "Shelby was a true Type A gamer and gave her access to a whole different world".
Inevitably, there were failures at home. Although it wasn't the first time Bryan, a father of four, cheated on his wife, it seemed like she was ready to forgive him again.
David Shaffer also seemed ready to work with Wintour to remedy the situation, although he was allegedly "upset and distraught" when he learned of his wife's affair from an answering machine message Bryan left him.
Wintour was previously married to David Shaffer from 1984 to 1999, pictured here in 1989
One of the last times they were photographed together as a couple was at the US Open tennis championships in 2018, when Anna Wintour was portrayed leaning away from Bryan
But in July of the following year, Wintour and Bryan were seen leaving New York's elegant Parc Vendome apartments together one morning. Wintour was wearing a chinchilla wrap that she had worn the night before.
Given their reputation for icy coolness, the scandal was greeted with glee by US gossip columnists.
Wintour's arch enemy Tina Brown, who was the editor of the now defunct Talk magazine, also published a damn piece that Wintour tried to stop, accusing Bryan of lacking transparency in his business affairs and borrowing millions to help his lavish lifestyle to finance "appalling" behavior towards women.
A British journalist who attended a party at Wintour's New York townhouse in 2002 described her as "starting the second act of her American dream with a rich new friend".
Wintour's divorce from David Shaffer had just come through, and as if to underscore the romantic change in her life, the party invitation was named Wintour and Bryan.
When asked about her relationship with Shelby, she simply said, “We are very happy” before adding that my main concern in breaking up with her husband was “the children. I just wanted to make sure it was as easy as possible for her . "
It was revealed that Vogue editor Anna Wintour has reportedly broken up with investor Shelby Bryan. Pictured: Shelby Bryan and Anna Wintour attend the Novak Djokovic Foundation New York Dinner on September 10, 2013 at Capitale in New York City
The couple kept their relationship largely private, though behind closed doors they are said to have bonded well with each other's children and maintained good relationships with their ex-spouses.
But then came a change in Bryan's once glittering professional fortune. In 2013, it emerged that he owed more than £ 1.2 million in property taxes and the IRS was slow to repay.
He reportedly lost much of his original $ 30 million fortune during the real estate recession.
The timing couldn't have been worse. After the couple raised millions of dollars for President Obama's re-election campaign, Wintour reportedly put their hopes on the US ambassador to the UK.
The appointment was not imminent.
On the professional networking website LinkedIn, Bryan, who attended Harvard Business School, describes himself as "self-employed" and has only 91 connections – a kind of defeat for the former CEO of ICG Communications who was once a major political figure.
Since then, the couple have been seen less together. It is not clear whether Wintour blames Bryan for not receiving Obama's nomination.
Of course, is it possible that the relationship just ran its course and that the lockdown only helped hasten its downfall?
But whatever the truth, the breakup takes place in the midst of something like an Annus Horribilis for Wintour.
Her former colleague and confidante André Leon Talley turned her on in May in his controversial treatise The Chiffon Trenches.
He accused her of using people and claimed that she frozen him because he was "too old, too overweight, too uncool" for her.
He went on to claim that there was an "endless" list of writers, stylists, and models she threw into a "shredded heap" during her powerful reign. He added: “She is immune to other than the powerful and famous who populate. . . Fashion.
"She has mercilessly turned her best friends into people who are the highest in their chosen fields."
Then, in June, at the height of the Black Lives Matter movement, Wintour had to apologize to Vogue publisher Condé Nast on allegations of racism.
In a memo, she admitted that during her 32-year tenure in Vogue, she had left "hurtful and intolerant behavior" unchecked and had not done enough to stand up for black workers and designers.
She added, “We have also made mistakes by posting pictures or stories that were hurtful or intolerant. I take full responsibility for these mistakes. "
Both professionally and personally, the world in which Wintour reigned supreme is changing rapidly.
For a woman known for consistency – daily tennis at 5:45 a.m., blow-drying twice a day, dozens of pairs of the same Manolo Blahnik heels – it must be nerve-wracking.
She will be 71 next month – an age at which she could be forgiven for putting her high-heeled feet up and enjoying the $ 35 million fortune she has amassed.
But on the way to the future, a single woman again, the woman nicknamed "Nuclear" Wintour – thanks to her bombproof reputation – does not seem to be showing any signs of slowing down.