Jeff Grant, the lawyer turned minister who counseled Skowron before he entered prison, now has a congregation in Bridgeport. Greenwich’s taste for schadenfreude, he says, has much to do with brute competition. “When anybody shows signs of weakness, everyone is feeding on the carcass—of the person or institution that’s been torn down,” he says. “In Bridgeport, when someone goes down for a crime, the community rallies around to help the family. Here, we cast them out on an iceberg.”

On a bright, windy afternoon last fall, Skowron climbed into the big white pickup truck that he uses to cart around Theo, the family’s exuberant golden retriever, for the drive to Bridgeport Correctional. When he arrived, Michael Christie, a chaplain at the prison, escorted him to a conference room where the new warden, Amonda Hannah, was having lunch with some corrections employees. “I want to thank you for letting me be here,” Skowron told her. “I need this. Even though things back home are in some ways returning to normal, I really feel most comfortable here—in prison.”

“Really?” Hannah said, skeptically. “That’s interesting.”

“In my community,” Skowron explained, “there’s a lot of judgment.”

Since his release, Skowron has spoken regularly about his journey—to college students, churchgoers, and Wall Street brokers—and he takes evident pleasure in recounting his story. “I had no idea how deeply in love I could fall with making money,” he told one audience recently. “But that was nothing compared to how deeply in love I was with myself. If I went to prison for everything I did, I’d still be there.” It is a redemption tale marred slightly by the fact that its teller’s lifestyle is enabled, in part, by the semi-piratical high jinks that the tale itself purports to repudiate. If Greenwich no longer offers him a sense of belonging, Skowron nonetheless has difficulty disavowing the success, however tainted, that once placed him among the town’s upper crust.

“Chip is being modest,” Christie told the prison employees. “He’s an orthopedic surgeon, and he started his own—”

“Hedge fund,” Skowron interjected.

“He was incredibly successful,” Christie said.

Skowron grinned. “My fund was one of the biggest at the time,” he said. “They made a movie about my fund.”

The prison chapel, where today’s gathering would take place, occupies a cinder-block classroom, with a wooden lectern up front and the 12 steps of Narcotics Anonymous hung by the door. With two other volunteers from the New Canaan Society, Skowron arranged plastic chairs in rows. Prisoners filtered in, wearing sweatshirts and khakis, and broke into small discussion groups, each led by a volunteer. Skowron often describes himself, in the years before his arrest, as an addict, beholden to a hungry ego that was itself a screen for dimly perceived despair. During the session, though, he said little, deferring to the inmates.

One man talked about his drug problems. Pudgy with glasses, in his 20s, he was struggling with the relationship between temptation and forgiveness. “I don’t want to rob this man,” he said. “Take this lady’s money out her purse.” Yet to satisfy his addiction, he found himself doing these things. If he had a disease, did he have a choice? If not, was he less culpable, more readily forgiven?

A big, bald 50-something inmate had become a Christian six years earlier, in Attica, only to wind up back inside on fresh charges. “I backslid,” he said. He had recently pleaded guilty to the new charges, and like Skowron, he’d been thinking about Matthew: “For whosoever will save his life shall lose it: and whosoever will lose his life for my sake shall find it.” Like Chip 1, the man Skowron met on his first day in prison, Skowron quoted to him from Romans: “For I do not do the good I want to do, but the evil I do not want to do—this I keep on doing.”