The Scandalous Affair
...She met Shelby Bryan. The millionaire telecommunications tycoon and investor was reportedly seated next to her at the Benefit Ball for the New York Ballet in 1997 and the chemistry was instantaneous. The only issue? They were both still married. Cue a hot and heavy two year secret affair, darling.
At the time, Bryan was a bigwig political donor for the democratic party, raising over a million dollars for candidates including Al Gore with glamorous fundraisers held at his Upper East Side home. He was also on Bill Clinton's Foreign Intelligence Advisory Board. In a 1999 article, New York magazine described him as a "flashy extrovert with undisguised social ambitions."
When the affair went public, gossip columnists swooned. Apparently Bryan's wife was quite used to his cheating, but Wintour's hubby was "upset and disturbed" when he learned of the affair thanks to a message left by Bryan on their answering machine (seriously? rookie move there).
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