Now they are trying to raise more than $500 million to turn their chain into a globe-spanning empire, which would make the firm a behemoth with condos in West Palm and Miami, a resort in Uruguay, clubs in Madrid and Tokyo and restaurants in Dubai.

But its star power and ambitious plans belie a family business tarred by secrets and scandals, including tax evasion, mob ties, an ugly war with the Rainbow Room’s owners, Harvey Weinstein’s predation and a years-battle over who even owns the Cipriani name.

Taylor Swift in Cipriani.
A young Taylor Swift dining at Cipriani. The family-owned hospitality empire has courted celebrities, royals and presidents for nearly a including Ernest Hemingway and generations of Kennedys.
Patrick McMullan via Getty Images
Bella Hadid entering Cipriani.
Stars like Bella Hadid have graced Cipriani’s countless red carpets.
GC Images
Kim Kardashian and Kourtney Kardashian at Cipriani.
Dolce Vita-loving Kim and Kourtney Kardashian attended the amfAR Gala at Cipriani Wall Street in 2019.
Getty Images

Along the way the family, based between Italy and the US, has made themselves friends with the glitterati — but not always with other diners.