The party known as Cocktails and Compliance—so called for mixing alcohol with tax advice—was thrown on a Friday evening in May, in a warehouse turned art gallery in Old San Juan. The host had kept his guest list confidential: It contained the names of hundreds of ultra-wealthy mainland Americans who'd moved to Puerto Rico to avoid paying taxes, most of whom were reluctant to advertise that fact. More than 1,500 mainlanders have established residency here since 2012, when the island rebranded itself as a tax haven, and the annual Cocktails is at the center of their social calendar.
At a high table, polishing off a bourbon on the rocks, sat a compact man in his 60s wearing a black T-shirt and black suede loafers, no socks. This was Mark Gold, the Florida-born kingpin of traffic-ticket contesting. Gold has attended Cocktails and Compliance every year since moving to Puerto Rico in 2016. "I was looking at different tax havens," he said, "Andorra, Lichtenstein, Monaco. But the problem is, you have to give up your U.S. passport. When I heard about this, it was too good to be true. But it's real. I live in paradise. I live at the Ritz-Carlton. I drive my golf cart to the beach club for breakfast. Then I go to my sunset yoga class on the beach."