After college, Skowron received a full scholarship to a combined M.D./Ph.D. program at Yale. During his residency in orthopedic surgery at Harvard, he used his vacation time to provide medical treatment in places like Kosovo and Guatemala. But he quickly grew disenchanted. No matter how many surgeries he performed, there was always pressure to do more. The older doctors he knew seemed discontent; many had failed marriages. His disillusion was bewildering, akin to losing faith. But Skowron had lost neither his sense of exceptionalism nor his outsize ambition. Soon after dropping out of Harvard, he decided to go into finance.

His timing was good. Eager to add an intellectual gloss to his already fantastically lucrative empire, Cohen was hiring professionals with Ivy League pedigrees and turning them into specialists in areas like energy and technology. Skowron’s background made him perfect for health care, one of Cohen’s favorite sectors. Instead of saving lives, Skowron could make a fortune tracking real-world events—the discovery of a new treatment, say, or the failure of a clinical trial—that might spark profitable volatility in health care stocks. In 2007, only six years after beginning his career in finance, he made $13.5 million.

Skowron’s fall was jarring. But he quickly had reason to think that, in pleading guilty, he had made the right decision. On his first day in prison, at a medium-security facility in Pennsylvania, another inmate extended his hand.

“Hi,” the man said. “My name is Chip.”

Unbelieving, Skowron replied, “My name is Chip, too.”

“Let’s be clear about this,” the man said. “I’m Chip 1, you’re Chip 2.” Noticing that Skowron was holding a Bible, Chip 1 quoted from Romans: “Just remember that all things work together for good.” They embraced, and Skowron felt confirmed in his newfound belief that he was being guided by God.

About 70 percent of Skowron’s fellow inmates were drug offenders, many of them poor young men of color. He saw gentler versions of Hollywood prison tropes: friction between inmates and guards, black-market intrigue, prisoners who liked to stir chaos just to thwart boredom. But the distance between his expectations of prison life and its reality was vast. Skowron had imagined that things would be horribly dull: rows of men staring into space, counting hours. In fact, prison was dynamic—rich with incident and culture. Some of what happened there seemed to shimmer with biblical resonance. One day, the prison was beset by a plague of snakes; they dropped from a light fixture onto men watching soap operas and rose out of a drain in the shower, where an inmate known as Joe the Greek was bathing. Then there was Chuck, a powerfully built gym buddy of Skowron’s, who began rapidly losing weight. By the time an appropriate doctor was consulted, his cancer was beyond curing.

It wasn’t all grim. One day, an inmate known as Gunz offered to give Skowron a tutorial on curried jack mack, a delicacy involving the bone-in mackerel sold at the commissary. Another prisoner, Kareem Burke, who went by Biggs, provided a pepper and an onion for the dish—a rare stash of fresh produce. Burke, who had cofounded Roc-A-Fella Records in the 1990s with Jay-Z and Damon Dash, was in prison for conspiring to distribute marijuana. Despite their differences, he and Skowron bonded quickly. Both men had lost their mothers at a young age; now, in quick succession, both came to consider themselves born again. Their high-profile friendship attracted others, and they were soon joined by a large group of inmates for regular meetings in Skowron’s bunk. The gatherings resembled AA meetings: discussions of sin, suffering, and the search for meaning and consistency in the wake of trauma. Burke spoke about his guilt for failing to support his older brother, who had been murdered years earlier. Others regretted infidelity. Many admitted their failures as fathers.

Prison ecology isn’t known for rewarding vulnerability, but the bunk became a foxhole, fostering a spirit of confession and mutual reliance. Among the men who met there, Skowron found he could expose himself in a way he had never been able to before. When news of his legal trouble broke, his Greenwich social circle had vanished. He was ejected from his country club, and his family felt humiliated by the publicity. Worried that he might be wearing a wire, former business associates wouldn’t speak to him. The abandonment surprised him. Skowron believed he’d had deep, nuanced relationships. On reflection, he saw that most of them had been based on the conference of status. Virtually none of his old friends visited him in prison.

As his relationships with the other inmates deepened, he became ashamed of his pride in his education and his wealth, which had insulated him in a cocoon of superiority. He saw that it had enabled a false, destructive worldview—the kind that, widely held, abetted mass incarceration. The people in prison were not who he had expected them to be, and prison, he now believed, was not where the vast majority of them belonged. Increasingly, he felt, they were his brothers.

Following his release, in November 2015, Skowron returned to live with his family in Greenwich, where they remained comfortably situated at the house on Doubling Road. There was the pool and there was the billiard room, with its Oriental rug and its Monaco Grand Prix posters. There was the view of the country club. Skowron’s office, paneled in dark wood, was like a stage set, accessorized with props from a prior life: framed credentials on the wall, a shelf dedicated to Ferrari paraphernalia, a photo with George and Barbara Bush.

Skowron was barred from working in the securities industry, but he quickly took ownership stakes in several businesses—apparel, medical marketing, health care, car sales—drawing on many of the same qualities that once made him an effective hedge-fund manager. Within two years, he found himself meeting with a top executive at HSBC, slipping almost seamlessly, he marveled, back into upper-corporate echelons. He enjoyed driving his silver Porsche Panamera, which smelled sweetly of his cologne. He kept his taste for fine wine.

But Greenwich was full of social trip wires. At Whole Foods or the park, Skowron was likely to encounter people he had caused to lose jobs or money. His neighbors were polite but distant. Not long after coming home, Skowron suggested to his wife that they have dinner at Mediterraneo, a favorite restaurant downtown. “I’m not going to that hedge-fund hangout!” she said. Ultimately, citing the Parmesan-encrusted halibut, he convinced her—only to run into Gil Caffray, a founding partner of FrontPoint.

Shortly before going to prison, Skowron had met with Jeff Grant, a former lawyer and onetime Greenwich resident who had spent 14 months in federal prison for wire fraud and money laundering. Grant, who had become a minister, counseled numerous hedge funders during Bharara’s insider-trading probe, and the chilly reception that greeted Skowron in Greenwich was familiar to him. It could seem in part like an aversion to self-knowledge; to interact with men like Skowron was to confront the sometimes suspect means by which the town maintained its status as one of the world’s most privileged enclaves. “It’s a mirror on themselves,” Grant says.

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