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20. Flavio Briatore and Elisabetta Gregoraci
Fraudster, alleged tax dodger and former Formula One manager Flavio Briatore now owns the Billionaire Club and is personally worth $150 million. Back in the day the unlikely playboy had a penchant for supermodels, but he found domestic bliss in 2008 when he wedded Elisabetta Gregoraci, a model 30 years his junior.