Life After White-Collar Crime

In the nineties, Jeffrey D. Grant had a law firm in Westchester County, a seat on the local school board, and an ownership stake in a bistro called, if you’ll forgive the irony, the Good Life. He was in his early forties, garrulous and rotund, and he gloried in his capacity to consume. Each year, he took his wife and daughters on half a dozen “shopping vacations,” though they sometimes neglected to open the bags between trips.

Grant had developed an early appreciation for personal displays of wealth and power. Born in 1956, the son of a marketing executive, he grew up on Long Island, graduated from SUNY Brockport, and worked his way through New York Law School as a shoe salesman. By then, his parents had divorced, and his father had moved in with Lynda Dick, a wealthy widow whose properties included one of the most storied mansions in Greenwich, Connecticut, a hilltop estate known as Dunnellen Hall. (It later became famous as the home of Leona Helmsley, the hotel magnate convicted of tax evasion in 1989, after a trial in which a housekeeper testified that Helmsley had told her, “We don’t pay taxes. Only the little people pay taxes.”)

Grant cultivated an ability to muscle his way into one opportunity after another. In law school, he approached the box office of a concert venue in Boston and, pretending to be the son of a music promoter, threatened revenge if he and three friends were not admitted free of charge. The brazen charade worked so well that the headliner, the rock-and-roll pioneer Gary U.S. Bonds, hosted the group backstage and, at the concert, sang “Happy Birthday” to one of Grant’s friends. As a lawyer, Grant specialized in real estate and corporate work and regarded himself as an “assassin.” In business and out of it, his philosophy was “Win, win, win.”

As he reached his mid-forties, however, Grant found himself unravelling. He had become addicted to painkillers—first Demerol, prescribed for a torn Achilles tendon, and then OxyContin. He was increasingly erratic and grandiose, betting wildly on dot-com stocks. In 2000, as his debts mounted, he started filching money from clients’ escrow accounts. The following year, after the terrorist attacks of September 11th, Grant applied for a disaster-relief loan from the Small Business Administration, claiming to have lost the use of an office near Ground Zero. That was a fiction. He received two hundred and forty-seven thousand dollars, which he used to cover personal and office expenses.

In July, 2002, under investigation for breaching his clients’ accounts, he surrendered his law license and was later disbarred. That summer, as he sat in a Ralph Lauren wicker chair in his greenhouse in Rye, he attempted suicide, swallowing forty tablets of Demerol. He survived, and entered drug and alcohol rehab. He and his wife moved to Greenwich, seeking a fresh start, but the marriage was too badly frayed to survive.

Grant’s undoing was not yet complete: officers of the Internal Revenue Service discovered the false claim on his loan application, and in 2004 a warrant was issued for his arrest. He pleaded guilty to wire fraud and money laundering, and a judge sentenced him to eighteen months in prison, chastising him for exploiting a national tragedy. On Easter Sunday, 2006, two friends drove Grant three hours west from Greenwich to Allenwood Low, a federal prison in the mountainous Amish country of central Pennsylvania. Grant quickly learned the rules: never take someone’s seat in the TV room or ask a stranger what landed him in prison. And he mastered the black-market economy that runs on “macks,” or foil packages of smoked mackerel, which sell for about a dollar in the commissary. He marked time mostly by walking—circling an outdoor track three or four hours a day, listening to NPR on headphones. “In the morning, all the airplanes from the East Coast would fly over going west, and at night they would come the other way,” he told me. “I would remember myself as a businessman.”

Grant was released to a halfway house in June, 2007, after fourteen months in prison. He had walked thirty-five hundred miles around the track and shed sixty-five pounds. He returned to Greenwich with no idea of what to do next.

Many people who have served time for white-collar felonies look to get back into business. Barely six months after the home-wares mogul Martha Stewart emerged from prison—she had been convicted of lying to investigators about a stock trade—she was hosting two new television shows. Grant, who no longer had a law license, tried applying himself to good works instead. He volunteered at rehab facilities that had helped him get sober. He joined the board of Family ReEntry, a nonprofit in Bridgeport, which aids formerly imprisoned people and their families, and he later served as its executive director. Hoping to improve his inner life, he studied for a divinity degree at Union Theological Seminary, in Manhattan. In 2009, he married Lynn Springer, a Greenwich event planner he had met in recovery. In 2012, they founded the Progressive Prison Project, a ministry focussed on white-collar and other nonviolent offenders.

As word of his experience spread, Grant started hearing from neighbors who were heading to prison or had recently returned and were seeking advice or companionship. At the time, a sense of alarm was animating conversations among businessmen along the Metro-North corridor: Preet Bharara, the U.S. Attorney for the Southern District of New York, had imposed a crackdown on insider trading, leading to more than eighty guilty pleas and convictions. Some of these cases were later invalidated by an appeals court, but Operation Perfect Hedge, as it was known, had punctured the realm of traders, analysts, and portfolio managers. “My phone would ring in the middle of the night,” Grant said. One financier, under indictment, called while hiding in his office with the lights out. “He said, ‘I’m afraid that people will recognize me on the street,’ ” Grant recalled. A reporter from Absolute Return, a trade publication for the hedge-fund industry, asked Grant, “How do Wall Street skills usually translate in prison?” His reply: “These skills are not only in large degree useless, they are probably counterproductive.” As he told me recently, “Business rewards a certain type of attitude and assertiveness—all things that will get you killed in prison.”

Grant, in his pastoral role for anxious brokers, fallen hedgies, and other wobbling pillars of late capitalism, came to expect fresh inquiries from desperate people each morning when he opened his e-mail. “Everyone going through this is freaking out, so they’re up all night, Googling,” he said. In the hope of nourishing his unlikely flock, Grant developed an ambitious reading list, which included “Letters and Papers from Prison,” by Dietrich Bonhoeffer, and “The Gulag Archipelago,” by Aleksandr Solzhenitsyn. If some callers found that Bonhoeffer’s words of resistance to the victims of national socialism did not seem immediately applicable, Grant also offered practical tips. Before reporting to prison, he advised them, mail yourself the phone numbers of family members and friends on the visitors’ list, because “you’ll be too discombobulated to remember them once you’re inside.” And remind your wife never to touch paper money on the morning of a visit; almost every bill bears traces of drug residue, which will set off the scanners.

In 2016, Grant established what he called the White Collar Support Group, an online meeting inspired by twelve-step programs for drug and alcohol addiction. He described the program as a step toward “ethics rehab” and, on his Web site, explained that it was for people who wanted to “take responsibility for our actions and the wreckage we caused.” In blunter terms, he told me that it was for “guys detoxing from power and influence.”

The first session attracted four attendees, including a hedge-fund manager and a man who had pilfered from his child’s youth-soccer club. But soon the program grew. In the next five years, more than three hundred people cycled through, either on their way to prison or just out and trying to reëstablish a semblance of their old order. Some of Grant’s flock were familiar from front-page scandals, born of Ponzi schemes, insider trading, and other forms of expensive corruption; others were virtually unknown to the public. This summer, I asked him if I could sit in on a meeting of the White Collar Support Group. He agreed, but alerted his members in advance, in case anyone wanted to preserve his privacy.

At seven o’clock one evening in July, I signed on to Zoom and found myself with twenty-eight people, mostly male and white, each identified by a name and a location. Meetings are free, though Grant suggests a donation of five dollars to his ministry. He draws a distinction between his work and the industry of white-collar “prison coaches” who offer bespoke services for a price. Among them, Wall Street Prison Consultants promises to “ensure you serve the shortest sentence possible in the most favorable institution.” It sells consulting packages at the levels of Bronze, Silver, and Gold, the finest of which includes “Polygraph Manipulation Techniques,” “Prison Survival Orientation Coaching,” and an “Early Release Package” that helps clients apply for a drug-treatment program to reduce the length of a sentence.

Grant, who now lives in Woodbury, Connecticut, appeared on camera wearing a pale-blue oxford shirt and sitting before a stone fireplace. As he called the meeting to order, we recited Reinhold Niebuhr’s Serenity Prayer, and then Grant reminded everyone of the rules: with few exceptions, anyone who talked for more than three minutes would hear a snippet of music—on this occasion, the Parliament funk classic “Mothership Connection (Star Child)”—signalling him to wrap it up. Surrendering control, Grant likes to tell his charges, may not come naturally.

Before the meeting, Grant had warned me not to expect universal contrition. “Almost everyone who contacts us has been successful, controlling, and perhaps narcissistic,” he said. “The elements that made them successful are also the elements that contributed to their demise.” Throughout their pre-indictment careers, aggression and rule-bending were considered strengths. In American culture, white-collar crime is often portrayed less as evidence of unfettered greed than as a misguided sibling of success.

By and large, the country’s governing class has encouraged that view. After the stock market crashed in 1929, Congress faced public pressure to curb the backroom manipulation that had helped devastate millions of shareholders. But Richard Whitney, the president of the New York Stock Exchange, a graduate of Groton and Harvard, told senators in Washington, “You gentlemen are making a great mistake. The exchange is a perfect institution.” In 1938, Whitney was caught embezzling from the New York Yacht Club, his father-in-law, and a number of others. He went to Sing Sing dressed in a double-breasted suit.

Not long after Whitney’s fall, the sociologist Edwin Sutherland devised the term “white-collar crime,” to describe wrongdoing committed “by a person of respectability and high social status in the course of his occupation.” Since then, each cycle of boom and bust has delivered new iterations of rapacious self-dealing, often indelibly linked to time or place, like schools of painting—the naked fraud of a Savings & Loan, the whimsical math of an Arthur Andersen. In 2001, following the accounting scandals at Enron and other companies, a publication called CFO Magazine quietly abandoned its annual Excellence Awards, because winners from each of the previous three years had gone to prison.

Since the turn of the millennium, the prosecution of white-collar crime has plummeted—but this should not imply a surge in moralism among our leading capitalists. After the attacks of September 11th, the F.B.I. began to shift resources toward counterterrorism. Meanwhile, Republican lawmakers cut the budget of the Internal Revenue Service so sharply that it had the same number of special agents in 2017 as it had half a century earlier, even though the national population has grown by two-thirds.

The effects of impunity have become more blatant since the Great Recession of 2007-09, when, infamously, almost no top executives went to prison—despite the loss of more than nineteen trillion dollars in household wealth. At the time, leaders at the Department of Justice claimed that they could not prove fraudulent intent by Wall Street titans, who were many layers removed from the daily handling of toxic securities. Jed Rakoff, a judge in the Southern District of New York, believes that this was a catastrophic misreading of the law. Executives, he argues, could have been prosecuted under the principle that they were “willfully blind” to patterns of abuse that enriched them. “Dozens of people defrauded millions of people out of probably billions of dollars,” Rakoff told me. The imperatives had less to do with compensating victims than with deterring crimes not yet conceived. “There are studies that are more than a hundred years old that show that the best way to deter any crime is to catch the perpetrators quickly,” he said.

In the years since, the failure to hold top executives accountable has become intertwined with historic levels of income inequality, a phenomenon that Jennifer Taub, a professor at Western New England University School of Law, calls “criminogenic.” In her 2020 book, “Big Dirty Money,” she wrote, “In our society, extreme wealth often confers tremendous power. So just as power tends to corrupt, so does excessive wealth.” But nothing expressed America’s ambivalence toward white-collar crime more eloquently than the election of Donald J. Trump, whose life and career as a business fabulist merited no fewer than a hundred and twenty-five mentions in “Big Dirty Money.” Under his leadership, federal prosecutions of white-collar crime reached an all-time low. In 2020, Trump delivered pardons and clemency to a slew of affluent felons, including Michael Milken, the junk-bond trader who had pleaded guilty to securities violations three decades earlier. Taub noted that the official White House announcement about the pardoned businessmen used the word “successful” to describe them four times.

Measurements of success, or something like it, haunt the conversations in the White Collar Support Group. In the Zoom meeting, one of the first people to speak up was Andy Tezna, a thirty-six-year-old former executive at NASA, who had been sentenced the previous week for fraud. Applying for COVID relief in the name of fictitious businesses, Tezna had collected more than three hundred and fifty thousand dollars, including loans issued under the Paycheck Protection Program. He used the money to finance a Disney Vacation Club time-share, a swimming pool ($48,962), and, to ease the social isolation of the pandemic, a French bulldog ($6,450).

“I got eighteen months,” Tezna told the group, glumly. “Definitely not the number I had in mind.” He was sitting beside a window covered by venetian blinds; he wore white earbuds and several days’ growth of beard. He was waiting for word on when to report to prison. In court, Tezna and his lawyer had presented him as an American success story gone wrong. His family had come from Colombia when he was thirteen and lived in an unfinished basement, while he helped his mother clean houses. Later, he earned a degree from George Mason University and landed a job at NASA, which paid him a hundred and eighty-one thousand dollars a year. In the job, he attended a space launch with members of Trump’s Cabinet and Elon Musk. “I just thought, My life is great,” he told the group.

To the judge, Tezna had framed his malfeasance narrowly, arguing, “I was bad at managing my finances.” The Justice Department thought it was worse than that. “These are not one-off mistakes,” a prosecutor told the court. “This was greed.”

A voice on the call piped up: “Hey, Andy? It’s Bill Baroni.”

It took me a moment to place the name. Then I remembered Bridgegate. In 2013, after the New Jersey governor Chris Christie appointed Baroni as the deputy executive director of the Port Authority, he was accused of helping to arrange a traffic jam on the George Washington Bridge, in order to punish the mayor of Fort Lee, who had refused to endorse Christie for reëlection. Baroni was convicted of fraud and served three months in prison. But he denied the charges, and eventually the Supreme Court overturned his conviction. Justice Elena Kagan wrote that, even though the evidence showed “deception, corruption, abuse of power,” the Bridgegate episode did not meet the legal threshold of fraud. Baroni’s victory in the Supreme Court gave him unique status in the group. “I got the exact same sentence you did—eighteen months,” he told Tezna. “I know what’s in your head today.”

For the next ninety minutes, the mood veered between grave and celebratory. Members swapped tidbits about mutual friends (“He got moved out of the private prison in Mississippi”) and applauded new ventures (“I signed a lease last week”). Grant has developed a soothing vocabulary—about strength regained and community embraced—which collided occasionally with members’ laments. “As a single guy, I can tell you dating sucks,” a man in Delaware said, “because the reactions from women run the gamut from ‘Oh, my God, you’re the worst form of life on earth’ to ‘Oh, that’s cool! Women like bad boys.’ ” A former hedge-fund manager in Chicago was still smarting over the publicity around his indictment. “Reporters were calling my parents and my brother,” he said. “I don’t even know how they got their phone numbers.” Members of the group arrive in disparate circumstances: some have managed to keep significant assets, while others are tapped out after restitution and legal expenses. According to Grant, the biggest distinction is between those who have been to prison and those who have not. Those who haven’t served time, he told me, are “sort of outside the club.”

More than a few members attributed their crimes to a kind of consumerist inadequacy. Craig Stanland, who defrauded the networking company Cisco of equipment worth more than eight hundred thousand dollars, told the group, “It was just pure shame from the beginning—not being able to tell my wife that I couldn’t afford that life style, all the way through getting arrested. And then the scarlet letter.” But Bill Livolsi, speaking from the Tulsa suburbs, who went to prison for his role in a Ponzi scheme that passed itself off as a hedge fund, had come to see his new circumstances as an unburdening. “I finally got a job after a year of being out. It makes a whopping fifteen dollars an hour, but I’ve never been happier with a job,” he said. “My focus isn’t on what flight I’m taking or where I’m going on this particular vacation. It’s on how my family’s doing and how I’m doing.”

Grant is solicitous. He asks new members to introduce themselves and, when needed, draws them out. Richard Bronson, a former Lehman Brothers stockbroker with cropped gray hair and a beard, said, “I used to work on Wall Street. I did very well.” In fact, Bronson became a partner at Stratton Oakmont, the firm made infamous by Martin Scorsese’s “The Wolf of Wall Street.” He moved to Florida and converted a small trading house called Biltmore Securities into a firm with five hundred employees. In Miami, he joined the boards of the ballet and the museum of contemporary art, opened a night club and started a magazine, and held court at an oceanside villa. But prosecutors said that all this was built on deceit; they accused him of running a boiler room that fed investors a stream of bogus stocks, causing losses estimated at ninety-six million dollars. Bronson disputed this figure, and insisted that he had repaid his clients. Nevertheless, he pleaded guilty to securities and wire fraud in 2002, and served twenty-two months in prison.

Bronson told the group, “This is really the first time I’ve ever been around people who have similar comeuppances.” He has been trying to revive his business career, launching 70 Million Jobs, a post-prison employment service, and an app called Commissary Club (“the exclusive social network for people with criminal histories”). “I’ve been out of prison for sixteen years, and I committed my crimes more than twenty-five years ago, and yet I wake up every morning with this gaping hole in my heart, out of regret for the things that I did.” He choked up momentarily and paused to collect himself. “I don’t suspect that I’ll get over this feeling,” he said, “and that saddens me.”

Others tried to buck him up. “I think we’re going to have to have a meeting about self-care soon,” Grant said.

Behind each new revelation of white-collar crime lurks an uncomfortable question about some of America’s most lucrative businesses: Are they attracting rogues or grooming them? Eugene Soltes, a professor at Harvard Business School, told me that regulations were partly to blame. “There is more white-collar crime today because there are more things that are criminal today than fifty years ago,” he said. Bribing a foreign official, for instance, was legal until the Foreign Corrupt Practices Act of 1977, and insider trading was rarely prosecuted until the nineteen-eighties. Today, those are among the most common offenses. But, Soltes went on, “I suspect that you might be asking the more intuitive version of this question. Given the same laws, same number of people, et cetera, is the proclivity for someone to engage in white-collar crime higher than it was fifty years ago?”

For his book “Why They Do It,” Soltes interviewed scores of people convicted or accused of white-collar crime. He said that he had found no evidence of a growing inclination to break laws. What has changed, though, is what he calls the “psychological distance” between perpetrators and their victims: “Business is done with individuals at greater length now, which reduces the feeling that managers are harming others.” In thought experiments, people agree to sacrifice the life of someone they can’t see far more readily than that of someone who stands before them. In Soltes’s interviews with people who had committed price-fixing or fraud, he found that many of them had never had a personal encounter with the victims.

In recent years, the lament that moral constraints have weakened has been voiced not just by critics of Wall Street but also by practitioners. In 2012, John C. Bogle, an iconic investor who founded the Vanguard Group and spent more than six decades in finance, wrote, “When I came into this field, the standard seemed to be ‘there are some things that one simply doesn’t do.’ Today, the standard is ‘if everyone else is doing it, I can do it too.’ ” Soon afterward, the law firm Labaton Sucharow conducted a survey of finance professionals, in which a quarter of them said that they would “engage in insider trading to make $10 million if they could get away with it.” Around the same time, Greg Smith, an executive director at Goldman Sachs, announced his resignation, decrying a “decline in the firm’s moral fiber.” Writing in the Times, he observed, “Over the last 12 months I have seen five different managing directors refer to their own clients as ‘muppets.’ . . . You don’t have to be a rocket scientist to figure out that the junior analyst sitting quietly in the corner of the room hearing about ‘muppets,’ ‘ripping eyeballs out’ and ‘getting paid’ doesn’t exactly turn into a model citizen.”

Researchers have elucidated the way that dubious behavior moves through a community. In the mid-aughts, the federal government brought criminal and civil cases for backdating stock options—manipulating records so that executives could take home a larger return than their options really delivered. Studies found that the practice had started in Silicon Valley and then infected the broader business world; the vectors of transmission could be traced to specific individuals who served as directors or auditors of multiple companies. An unethical habit spreads in encounters among neighbors and colleagues, through subtle cues that psychologists call “affective evaluations.” If people are rising on one measurement (profit) even as they are falling on another (ethics), the verdict about which matters more will hinge on the culture around them—on which values are most “exalted by members of their insular business communities,” Soltes observed in his book. As he told me, “If you spend time with people who pick locks, you will probably learn to pick locks.”

In 2013, prosecutors announced an indictment of S.A.C. Capital Advisors—named for its founder, Steven A. Cohen—calling it a “veritable magnet for market cheaters.” Cohen, like a considerable number of his peers, lived in Greenwich. In the previous decade, as the hedge-fund industry surged in scale and profits, the rise of the Internet had allowed funds to leave Wall Street, and many moved to southern Connecticut to take advantage of favorable tax rates and easy commutes. By 2005, hedge funds had taken over two-thirds of Greenwich’s commercial real estate.

After the charges against Cohen were announced, David Rafferty, a columnist for Greenwich Time, a local paper, published a piece with the headline “Greenwich, Gateway to White-Collar Crime.” He wrote, “A few years ago you might have been proud to tell your friends you lived in ‘The Hedge Fund Capital of the World.’ Now? Not so much.”

Rafferty, in his column, described a “growing sense of unease in certain circles as one hedgie after another seems to be facing the music.” Cohen, however, faced the music for a limited interlude. Under an agreement brokered with prosecutors, his firm pleaded guilty to insider trading and was sentenced to pay $1.8 billion in penalties. After a two-year suspension, Cohen returned to the hedge-fund business, and made enough money to buy the New York Mets. The price was $2.4 billion, the largest sum ever paid for a North American sports franchise.

Luigi Zingales, a finance professor at the University of Chicago, told me that he wishes his profession spoke more candidly about accountability and impunity. Most of the time, he said, business schools find “every possible way to avoid the moral questions.” He added, “I don’t know of any alum that has been kicked out of the alumni association for immoral behavior. There are trustees of business schools today who have been convicted of bribery and insider trading, and I don’t think people notice or care.” He went on, “People are getting more and more comfortable in the gray area.”

One of the longest-running members of the White Collar Support Group is a lean and taciturn man in his forties named Tom Hardin—or, as he is known with some notoriety in Wall Street circles, Tipper X. Not long after graduating from business school at Wharton, Hardin went to work for a hedge fund in Greenwich. He had much to learn. Almost instantly, he began hearing that some competitors, such as the billionaire Raj Rajaratnam, were suspected of relying on illegal tips from company insiders. (Rajaratnam was later convicted and sentenced to eleven years.) In 2007, after Hardin became a partner at Lanexa Global Management, a hedge fund in New York, he got his own inside tip, a heads-up on an upcoming acquisition, and he traded on the information and beat the market. He repeated similar stunts three times. “I’m, like, I would never get caught if I buy a small amount of stock,” he told me. “This is like dropping a penny in the Grand Canyon.” He went on, “You can say, ‘I’m highly ethical and would never do this.’ But once you’re in the environment, and you feel like everybody else is doing it, and you feel you’re not hurting anybody? It’s very easy to convince yourself.”

One morning in 2008, Hardin was walking out of the dry cleaner’s when two F.B.I. agents approached him. They sat him down in a Wendy’s nearby and told him that they knew about his illegal trades. He had a choice: go to jail or wear a wire. He chose the latter, and became one of the most productive informants in the history of securities fraud. The F.B.I. gave him a tiny recorder disguised as a cell-phone battery, which he slipped into his shirt pocket, to gather evidence in more than twenty criminal cases brought under Operation Perfect Hedge. For a year and a half, his identity was disguised in court documents as Tipper X, fuelling a mystery around what the Times called “the secret witness at the center of the biggest insider-trading case in a generation.”

In December, 2009, Hardin pleaded guilty, and his identity was revealed in court filings. He had avoided prison but become a felon, which made features of a normal life all but impossible, from opening a brokerage account to coaching his daughters’ soccer team. He was unsure how he could earn a living. “I would ask my attorney, ‘Are there any past clients you can connect me with who’ve got to the other side of this and are back on their feet?’ He was, like, ‘Sorry, not really.’ ”

He heard of Grant’s group through a friend. “I had no idea something like this existed,” Hardin said. “Jeff was the first one who said, ‘Hey, here’s a group of people just in our situation. Come every Monday.’ ” In 2016, the F.B.I. called him again—this time, to invite him to brief a class of freshman federal agents. Hardin’s lecture at the F.B.I. led to more speeches—first for free, and eventually for a living. He was back on Wall Street, as a teller of cautionary tales. It was not quite motivational speaking; his niche, as he put it, dryly, was “overcoming self-inflicted career decimation.”

In his dealings with his peers, Hardin has learned to distinguish who is genuinely remorseful from who is not. “I’ll hear from white-collar felons who tell me, ‘I made a mistake,’ ” he told me. “I’ll say, ‘A mistake is something we do without intention. A bad decision was made intentionally.’ If you’re classifying your bad decisions as mistakes, you’re not accepting responsibility.”

In the era of rising discontent over injustice, some Americans accused of white-collar crimes have sought to identify with the movement to curb incarceration and prosecutorial misconduct. So far, the spirit of redemption has not extended to the members of the White Collar Support Group, whose crimes relate to some of the very abuses of power that inspire demands for greater accountability. For the moment, they are caught between competing furies, so they rely, more than ever, on one another. “A white-collar advocate still doesn’t have a seat at the table of the larger criminal-justice conversation,” Grant told me. “We exist because there’s no place else for us to go.”

The group members’ predicament rests on an unavoidable hypocrisy: after conducting themselves with little concern for the public, they find themselves appealing to the public for mercy. Baroni, the former Port Authority executive, told me, “I can’t go back. All I can do now is to take the experiences that I’ve had and try and help people.” His regrets extend beyond his scandal. He had been a New Jersey state senator, and, he said, “I voted to increase mandatory minimum sentencing. I never would have done that had I had the experience of being in prison.”

Baroni recently helped establish a nonprofit called the Prison Visitation Fund, which, if it can raise money, promises to pay travel expenses for family members who can’t afford to travel. His partner, and first funder, in the endeavor is a former lawyer named Gordon Caplan, who is one of fifty-seven defendants in the college-admissions scandal known as Operation Varsity Blues. Caplan was a co-chairman of the law firm Willkie Farr & Gallagher until 2019, when he was indicted for paying seventy-five thousand dollars for a test proctor to fix his daughter’s A.C.T. exam. “To be honest,” Caplan said, on an F.B.I. recording at the time, “I’m not worried about the moral issue here.” He pleaded guilty and was sent to a federal prison camp in Loretto, Pennsylvania, a minimum-security facility that houses low-risk offenders with less than ten years left on their sentences.

Caplan was one of America’s most prominent lawyers, but he never paid much attention to complaints about the criminal-justice system until he was in the maw of it. “What I saw is other people going through a system that’s built for failure, built for recidivism,” he told me recently. Caplan had presumed that incarcerated people had reasonable access to job training and reading materials. He was wrong. “The only courses that were offered were how to become a certified physical trainer and automotive repair.” Inmates could create their own classes, and Caplan taught a short course on basic business literacy. “I had fifteen to twenty guys every class,” he said. “ ‘Do I set up an L.L.C. versus a corporation?’ ‘Should I borrow money or should I get people to invest in equity?’ ” Since getting out, Caplan has been alarmed by the barriers that prevent even nonviolent felons from rebuilding a life. “I have assets and I have family and I’ve got all that. But how does a guy who came out for dealing marijuana even start a painting business?”

Hearing Caplan, Grant, and others talk about their sudden understanding of America’s penal system put me in mind of the work of Bryan Stevenson, a leading civil-rights lawyer and the founder of the Equal Justice Initiative, which advocates for criminal-justice reform. He beseeches people to “get proximate”—to step outside the confines of their experience. Stevenson often quotes his grandmother, the daughter of enslaved people, who went on to raise nine children. “You can’t understand most of the important things from a distance, Bryan,” she told him. “You have to get close.”

But getting close is not the same as staying close. After serving twenty-eight days in prison, Caplan returned to Greenwich, where he lives in a seven-million-dollar Colonial, down the hill from the old Helmsley estate. For all his recent concern about the failings of criminal justice, I suspected that the country might have more to learn from him about his own failings. What, I asked, possessed him to pay someone to falsify his kid’s college-admissions test results? He was not eager to answer. “Achievement, I think, is like a drug,” he said, after a pause. “Once you achieve one thing, you need to achieve the next thing. And, when you’re surrounded by people that are doing that, it becomes self-reinforcing. When you also have insecurities, which a lot of highly motivated people do, you’re more apt to do what is necessary to achieve. And it’s easy to step off the line.” Caplan convinced himself that paying to change his daughter’s test results was scarcely more objectionable than other forms of influence and leverage that get kids into school. “I saw what I believed to be a very corrupt system, and I’ve got to play along or I’ll be disadvantaged.”

Greed, of course, is older than the Ten Commandments. But Caplan’s experience illuminated the degree to which greed has been celebrated in America by the past two generations, engineered for lucrative new applications that, in efficiency and effect, are as different from their predecessors as an AR-15 rifle is from a musket. If you have the means, you can hone every edge, from your life expectancy to the amount of taxes you pay and your child’s performance on the A.C.T.s. It’s not hard to insure that the winners keep winning, as long as you don’t get caught.

In the most candid moments on the Zoom call, people acknowledged the damage that their crimes had inflicted on their spouses and children. Seth Williams, a former district attorney of Philadelphia, pleaded guilty in 2017 to accepting gifts in exchange for favors, and served nearly three years in federal prison. Afterward, he struggled to find an apartment that would accept a felon. His first job was stocking shelves overnight at a big-box store; eventually, after an online course, he became a wedding officiant for hire. He was not surprised that former colleagues avoided him, but watching the effects on his family left him in despair. “It affects all of us in how our children are treated at their schools, on the playground,” he said. “Some of our spouses, people want nothing to do with them.”

Not long ago, Grant regained his law license in the State of New York, based largely on his work as a minister and as an expert on preparing for prison and life after. Nineteen years after being disbarred, he rented an office on West Forty-third Street in Manhattan and started practicing again, as a private general counsel and a specialist in “white-collar crisis management.” At seminary, he had studied migrant communities, and he came to see an analogy to people convicted of white-collar crimes. “We have one foot in the old country, one foot in the new,” he told me. If they hoped to thrive again, they would have to depend on one another. “Greek Americans funded each other and opened diners. They lift each other up.” He went on, “The problem we have in the white-collar community is that people who have been prosecuted for white-collar crimes want to become so successful again that they are no longer associated with it. I’ve approached some of the household names, and to a one they’ve rejected it.” I asked him if he was referring to people like Michael Milken and Martha Stewart. Grant demurred. “My mission is to help people relieve their shame, not to shame someone into doing something.”

Grant will tell you that shame does not help in recovery. But America’s record in recent years suggests that, in the nation at large, too little shame attaches to white-collar crime. If the country has begun to appreciate the structural reasons that many of its least advantaged people break the law, it has yet to reckon with the question of why many of its most advantaged do, too. Members of Grant’s group usually come to accept that they got themselves into trouble, but more than a few hope to follow Milken and Stewart back to the club they used to belong to—winners of the American game.

As the Zoom meeting wound down, Grant asked Andy Tezna, the former NASA executive on his way to prison, if there was anything else he wanted to say. “I had a lapse of judgment,” he began, then caught himself and confessed impatience with the language of confession. “I’m so tired of using that word, but, whatever it was that led me to make my mistake, it’s not going to define me for the rest of my life.” He thanked the members of the group for helping him get ready to embark on his “government-mandated retreat.” He’d see them afterward, he said, “once I’m out, a little wiser, a little older, with a few more gray hairs.” ♦