Cindy Crawford’s Family Connection to Amal and George Clooney Involves $1M Gift and Two Holiday Homes

George Clooney’s squad is the stuff of legend – Brad Pitt, Matt Damon, Julia Roberts, and of course, Rande Gerber and Cindy Crawford. But Cindy and Rande’s connection with George and wife Amal goes much deeper than just friendship, as their relationship has spanned four decades, a business deal, weddings, and children.

Cindy, the OG supermodel, married Rande in 1998, but Rande’s friendship goes back farther with George, with the pair meeting in the mid-1990s at Paramount Hotel hot spot, the Whiskey.

Over their years of friendship, they often vacationed together, with the group together in Italy in 2002 when George fell in love with Lake Como and decided to purchase his $100 million lakeside villa. In 2009, George, Rande, and Cindy also purchased a compound in Mexico, which featured two houses – one for each family – and were designed by famed Mexican architect Ricardo Legorreta.

The original plan was for the group to share one home, but Cindy reportedly encouraged them to build two homes on the same piece of land. ‘We have breakfast at my house, lunch at his, dinner at ours,’ Rande later joked, calling them ‘one big family’.

That family grew in 2013 when, as George and Rande began making plans to launch their tequila company Casamigos together, George was also falling in love with Amal Clooney, a human rights lawyer whom he met at a dinner party. Calling Amal a ‘great addition to the family,’ Rande once suggested that George’s perpetual bachelorhood was never about timing but about waiting for the right person.