PALM BEACH, Florida — Howard Kessler drew a box on a piece of paper and scribbled lines shooting out from all four sides. “When I dealt with banks, in one meeting, I remember this guy said, ‘Look, Howard, I’m in here. You’re all over there!’ ” Kessler told me. “I think outside of the box. I think differently.”
Kessler’s way of thinking helped make him an architect of affinity credit cards back in the 1980s. Sponsored by airlines, colleges, department stores, unions, and other organizations, affinity cards paved the way for airline frequent-flyer programs, credit card perks, and the rise of a cashless society. He became a billionaire—and bought a mansion here for $30 million in 2001.
No one had ever paid so much for a home in Palm Beach, including Kessler’s friend, Donald Trump. “Donald thought I was an idiot for paying that much,” Kessler said as we sat in the main house that overlooks the ocean, not far from his two swimming pools, a green clay tennis court, a greenhouse, gazebo, and guesthouse. “It’s worth 10 times more now,” he added.
