One humid Tuesday in July, I summited the highest point on Grand Cayman, an eight-story dump known affectionately by the locals as Mount Trashmore. From the top of the foul mound — a collection of almost every piece of garbage discarded on the island since it went all-in on financial services in the 1960s — I imagined I could just make out the enshrouded beach estate of the secretive investor Kenneth Dart.



I had been on Grand Cayman for more than a week, but I was no closer to speaking with him than when I first arrived. The heir to a famously private foam-container dynasty and a reclusive businessman in his own right, Mr. Dart apparently hasn’t spoken to the press since 1993. Though he has lived on Grand Cayman for 25 years and is widely believed to be the biggest private landholder on the archipelago, almost nobody I interviewed was sure if they had seen him. Residents compared him to Batman, Howard Hughes, a Bond villain and both Warren and Jimmy Buffett.

Mr. Dart lives on Seven Mile Beach, in an old hotel — the entire hotel — once known as the West Indian Club. He acquired the property in 1994 after renouncing his United States citizenship, a tax dodge so audacious it inspired federal legislation. Though Cayman was initially a refuge for the financier, Mr. Dart, who is thought to be 64, has taken to his adopted home with zeal. With his fortune and his company, Dart Enterprises, he has increasingly come to define the islands’ future.

In 2007, he opened a major development, a sprawling mix of retail and entertainment venues called Camana Bay, and began amassing a portfolio of high-end properties. His list now includes the Ritz-Carlton, the Yacht Club and a new Kimpton resort. In February, his group proposed a $1.5 billion “iconic skyscraper” that would rival the Eiffel Tower and the Burj Khalifa of Dubai.