In early 2006, before the indictment and the headlines, before he was abandoned by most of the people he knew, Joseph Skowron III and his wife, Cheryl, were living in a tidy three-bedroom ranch home in Greenwich, Connecticut. In the early 20th century, Greenwich attracted flocks of industrialists and their descendants—Rockefellers and Morgans, beneficiaries of Carnegie Steel—who built manor homes on generous acreages. Always prosperous, the town was in the midst of another boom, and Skowron, who goes by Chip, was a member of the town’s new elite, a partner in a hedge fund called FrontPoint Partners. Since 2000, drawn by Connecticut’s relatively low taxes, the hedge funders had all but taken over Greenwich, occupying much of its office space and replacing its stately Victorians with garish mansions, priced to move at $15 million. As VANITY FAIR observed at the time, “The people who can afford to live in Greenwich these days run hedge funds.”

Among the aggressive, often eccentric billionaires who dominated the town, a peacock spirit prevailed. Paul Tudor Jones II, the founder of Tudor Investment Corporation, built a Monticello-like mansion so imposing as to overshadow the yacht club next door. Down the shoreline, Edward Lampert, the founder of ESL Investments, bought a $21 million home, only to tear it down and erect a sprawling new estate in its place. And in the rural backcountry, Steven Cohen assembled a 32,000-square-foot spread that included an ice rink to rival Rockefeller Center’s.

At 36, Skowron didn’t quite have ice-rink money. He had begun his career in finance just five years earlier, as an analyst at Cohen’s SAC Capital Advisors. But before long, he was overseeing some $1 billion in assets at FrontPoint, where one of his partners was Steve Eisman, the shrewdly bearish housing-market investor profiled by Michael Lewis in The Big Short. Cheryl was expecting the couple’s fourth child, and Skowron wanted a home to reflect his success. In early 2006, he bought a three-acre tract on Doubling Road, a quiet, curving lane lined with old trees and low stone walls, for $4.1 million. Across the street lay Greenwich Country Club, whose membership roll included Gerald Ford, Tom Seaver, and various Fortune 500 executives. Skowron hired an architect to design a New England shingle-style home of more than 10,000 square feet. Completed, it had seven bedrooms, four fireplaces, a pool, a wine cellar, and a seven-car garage. Views stretched to Long Island Sound.

Cheryl had no interest in the Greenwich social circuit, with its acquisitive pulse. But Chip reveled in it. The Skowrons, already members at one of the town’s several country clubs, applied to join another. Greenwich has a dense calendar of charity galas, and Skowron made sure that he and Cheryl turned up at the right events. He joined the Monticello Motor Club, a speedway in upstate New York where Jerry Seinfeld is a member. One item in his auto collection, an Alfa Romeo 8C Spider, once appeared on a list of Greenwich’s most expensive cars. He traveled widely and lavishly. In Paris he favored the Plaza Athénée; in Barcelona, the Hotel Arts.

Among friends and family, Skowron was known to be generous, loyal, and fun-loving—a griller of burgers and sharer of beers. But he was emotionally exhausted, wrung out by the pressure of keeping up appearances and increasingly troubled by a sense of emptiness. “I wanted to be somebody that was important,” he recalls. “I wanted to accomplish, succeed, to be satisfied. It was all illusory.”