Gordon Caplan’s Comeback: Is Redemption Still Possible In America?

In April, when I called Rabbi Aaron Lipskar, he was a little distracted.

Lipskar is director of the Aleph Institute, a $7 million nonprofit, headquartered in Florida, that serves prisoners, military personnel and other isolated people. I needed to ask Lipskar about a story I was working on. He wanted to tell me about “Chaya,” (not her real name).

“It’s a Passover miracle,” Lipskar said.

The first part of Chaya story is terribly common, today in America: Abused as a child, she became a thief to support her drug habit, and to support a manipulative boyfriend. Because of California’s Three Strikes law, she was facing 45 years to life. Aleph intervened, successfully making the case to a judge to have her sent to a one-year rehab instead.

Lipskar was thrilled because that very day he had heard she had graduated from rehab, and would be released, and her mother was waiting to help her through the next steps. It was a happy-ending story made possible, in part, by a man named Gordon Caplan, who had become vital to Aleph’s work over the past two years. “Whenever we need something, Gordon is there,” said Lipskar.

Caplan was the reason for my call. He’s, in part, what this story is about.

The Varsity Blues Scandal

His name might ring a bell, if you move in certain circles.

Gordon Caplan was one of the wealthy Americans who went down in the 2019 Varsity Blues scandal. More than 50 people were convicted for a scheme that enabled people to rig tests or to fake athletic records to get their kids into top colleges.

Ensnaring celebrities including Felicity Huffman and former executives of investment giants PIMCO and TPG Growth, the scandal lingered in the news for years, even through COVID, and was the subject of a podcast and a Netflix documentary.

Varsity Blues struck a deep nerve among many Americans. The scam showed them what they long suspected: Top colleges said they cared about merit, but what they really cared about was money. No matter how good, hard-working or smart your kid was, they weren’t going to get a fair shot if you couldn’t pay for it.

Though, the college admissions system, as miserable as it is, is not the subject of this story. Nor is this story a diatribe about privileged parenting in America.

The federal judge in the Varsity Blues case, Indira Talwani, seemed aware of the simmering anger against the defendants. On Oct 3, 2019, she sentenced Caplan to one month in prison and a $50,000 fine. In court that day, Caplan said he took full responsibility for paying $75,000 to increase his daughter’s ACT score (unbeknownst to her).

“I sincerely apologize to all students and families who are hurt by my conduct. They deserve better. I am deeply ashamed that I have in any way, in any way contributed to the broader concerns and cynicism in society that the system is rigged in favor of the rich. It's an anathema to me, and the fact that I'm involved in this disgusts me every day. I now face and accept the consequences of my actions without excuses or blaming anyone else.”

Many people might doubt that Caplan was sincere. That’s what you would say when you are facing a judge who is about to sentence you, if you are smart. Before he was caught in a wire tap, Caplan was co-chairman of Willkie Farr & Gallagher, a law firm with 1,000 attorneys and 13 global offices.

Talwani said the combination of prison time and Caplan’s public contrition made it seem likely to her that he would understand morality, rules and law better. And in a nod to the media circus, Talwani said, “hopefully the punishment will weigh against further consequences.” Maybe, she seemed to be saying, the prison time –atypical for first-time nonviolent offenders — was a way to help everybody move on.

That’s what this story is about: Moving on. It’s partly about Gordon Caplan, and it’s partly about America, and whether we believe in leaders who can redeem themselves, who can take life’s experiences, acknowledge a mistake, and come out the better person.

After he got out of prison, Caplan established a small strategic advisory firm called Dutchess Management. He hired other people who have come out of rough patches, and began taking on philanthropic causes, including helping prisoners and prison reform.

Whether you’re inspired by Gordon Caplan is up to you. I was, by the end of this story.

What It’s Like In Prison

Caplan spent the last month of 2019 at a prison “camp” – the lowest level of security – in northern Pennsylvania.

He had to go through “the process” as he entered FCI Loretto. That meant strip search and cavity search, all his clothes taken, no toiletries allowed until commissary day a week later. Then he was given a top bunk, which he had trouble climbing up to.

He was in for 28 days.

One of the other prisoners called him “28 days.” Like, “Hey 28 days,” Caplan told me in an interview a couple of months ago. Another prisoner’s nickname was “Gordo.” When Caplan heard it, he thought he was in trouble.

In prison, Caplan taught classes to help people start businesses. Almost half the 150 people or so in Loretto’s prison camp showed up for the classes. Entrepreneurship is one of the most viable paths for felons, post prison.

Learning via prison sounds a lot like Piper Chapman in Orange Is The New Black, right? But Caplan’s life is real, for one thing, and for another, Caplan is a man.

When he got out, Caplan didn’t feel redeemed. He thought he would kill himself. Men, especially white men, sometimes have more fragile identities, often based around their work. They more often refuse mental health help, too. White men accounted for almost 70% of the 130 suicide deaths a day in 2020, according to the American Foundation for Suicide Prevention.

Caplan had been humiliated. His license to practice law had been revoked for two years. He had violated his own code, as he saw it.

That he didn’t die by his own hand, he told me in an interview, was due to the supportive people around him. He didn’t want to cause more pain to his family and make the situation worse. He also remembered something his father, a physician who came to his sentencing, said during his growing-up years.

“I remember my father sitting next to me on the bed. He was going through a hard time,” Caplan said. “He told me the key to life is tenacity.”

The question became, then, how was he going to go forward?

The Narrative Of Redemption

Though he didn’t define it this way –I think it would seem arrogant to him — Caplan began seeking something that has grown increasingly difficult to find in American life: redemption. Of course, redemption still exists in people’s personal and spiritual lives. But outside of any particular faith, society has an interest in healthy redemption narratives, too. They encourage honesty and good works, and give us a shared touchstone.

When we have a healthy redemption narrative, we disagree about a lot, but we can agree on one thing: We are all hopelessly flawed.

But, today, “we live in a less forgiving age than perhaps we once did,” said Dan P. McAdams, the interim dean of the School of Education & Social Policy at Northwestern University, and the author of The Strange Case of Donald J. Trump: A Psychological Reckoning.

The possibility of redemption is further complicated by politics and class in today’s America. “If the hero of the redeemed sinner story is rich or a white evangelical Christian, liberals probably will turn their backs,” wrote McAdams in an email. “If the hero is poor or black or an elite of some kind, many conservatives will scoff.”

“In the case of Gordon Caplan … many Americans may be reluctant to admire the comeback story of a man who was so economically advantaged in the first place and yet cheated so flagrantly to provide his privileged daughter with even more advantages.”

From Cherry Tree To Iran Contra To Donald Trump

The decline in any kind of shared redemption narrative, especially for leaders, is clear when you look over time. George Washington and the cherry tree may have been apocryphal, but it was a redemption narrative. Here’s Ronald Reagan on the Iran Contra Scandal, referencing the idea of redemption:

“Now, what should happen when you make a mistake is this: You take your knocks, you learn your lessons, and then you move on. That’s the healthiest way to deal with a problem… You know, by the time you reach my age, you’ve made plenty of mistakes. And if you’ve lived your life properly — so, you learn. You put things in perspective. You pull your energies together. You change. You go forward.”

These days? The idea that we all make mistakes has almost disappeared from a leader’s playbook – especially, unfortunately, from the playbooks of the people who make up most of the leadership class of America, white men. When Caplan emerged from prison, he looked around for a model he could follow to rebuild a life of character.

So you have Bill Clinton, who lied because he thought he could get away with it, and Donald Trump, who couldn’t do anything other than lie. The left’s acceptance of Bill Clinton leads straight to the right’s acceptance of Donald Trump.

In the business world, meanwhile, narcissism and greed define most leaders. One of Elon Musk’s chief talents appears to be for bullshitting. Martha Stewart came back, but it wasn’t in the interests of becoming a better person, it was about her brand. Michael Milken has done a lot of good, but in a way that’s so distastefully narcissistic that it took people years to acknowledge what he could contribute.

That Caplan expected a redemption playbook at all is a sign of his privilege. Most people who aren’t at the top of the social hierarchy carve their own paths, aiming for success against the odds, much earlier in their lives. But to his credit, when it dawned on Caplan that he wouldn’t find a ladder to climb, he started to push ahead, anyway. He connected with a few sentences from Theodore Roosevelt’s The Man in The Arena:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming.”

He said he didn’t like the quote because he wanted credit – “society doesn’t owe me,” he said. “It owes other people.” But the quote told him that everybody fails. It normalized failure, which helped him go forward.

There’s a current prevailing mindset, based on an informal mix of psychology, nurture and the eternal nature of Google’s memory, that people don’t change (much). Against that mindset, against the odds, and against the stereotypes of rich entitled men, Caplan has begun to change.

“I’m doing this to be valid,” he said. “I couldn’t think of anything else to do.”

The Narrative of Redemption

When a friend of Caplan’s reached out to tell me how much he had changed, I thought, cynically, that they probably wanted to use the media to create a veneer of transformation that would help Caplan slip back up to his old life. That’s what we call in the business, “a puff piece.” That was not very appealing to me.

But the friend went on to argue that “we need stories like this that show people that there can be a second chapter in life.”

“(Gordon’s) commitment to learning from his experience every day inspires a lot of us to believe we can all reflect on our past and put in the hard work of making the best version of ourselves,” the friend told me later. (He asked that his name not be used).

I don’t know if Caplan is telling the truth about a change of heart; there is no chance of me ever really knowing that. But I decided it didn’t matter. If we’re to move forward, we have to start giving people second chances – even people we don’t like, people with awful track records, and people on the far side of the culture wars. We might even have to do it proactively, though that’s a lot harder.

Rationally speaking, we need to believe in redemption. The alternative is to live with the lies, and the liars.

Finding Grace

Still, I probably wouldn’t have written this story if it weren’t for a man named Dana Ball. It took me a while to find him. But I wanted to talk about this question of moving on with someone who’s had to move on with 100-pound weights strapped on: poverty, childhood trauma, and race in a racist society.

Ball was in foster care as a child, dropped out of high school and worked for five years, including as an assistant manager at a RentWay for $12.50 an hour. He started selling drugs to make ends meet. As the profits grew, he opened a restaurant in the Pittsburgh area. He received a nearly 11-year sentence for running a business bringing in marijuana and at one point, cocaine from California. After he was caught, he was denied bail and sent to a private prison. He finally decided to cut a deal after a visit from his 5-year-old daughter. “Daddy, I’m going to bring a rock in and break the glass,” she said.

He spent time at Loretto while Caplan was there. In prison, he said, drug criminals look down on the white-collar criminals. “The drug dealers tell the white-collar criminals: You stole money from old people,” said Ball. “It’s a mutual thing.”

After Ball got out, the woman who had been his fiancée married him. He’s back with his kids now. He has a job making wheels for semitrucks. Last year he earned more than $85,000.

I asked Ball how he felt about men like Gordon Caplan, whose lives from birth right on through to the consequences of any mistakes they’ve made, are so much easier – at least, outwardly.

“It’s not their fault. It’s the system,” he texted back. I pressed him a bit. “How is it that you’re not bitter toward people who have had it so much easier than you?”

“If you live feeling bitter, are you really free?” he texted back.

If Dana Ball could offer grace to Gordon Caplan, I figured your typical suburban white upper middle-class person could, too.

Or maybe not.

The Media of Today

Caplan – or anybody from the elites seeking acceptance or redemption from the left or mainstream media — is up against a lot. Just like it’s a problem that we can’t create a narrative that allows leaders to fail, it’s also a problem to paint targets on entire classes of people, even the rich people.

Caplan had been the target of a particularly cruel story in The Atlantic. The article was headlined, “They Had It Coming.” The author, Caitlin Flanagan, mocked Caplan mercilessly, from his house in Greenwich to his school, “sweaty-browed Fordham” to his wife, to the fact that he paid more than actress Felicity Huffman in the scam. Flanagan wrote:

(Rick Singer) charged Caplan $75,000 for the testing scam, yet he charged Felicity Huffman only $15,000. (Perhaps The American Lawyer needs to cast a wider net when selecting its Dealmakers of the Year.)

One reason the redemption narrative is shrinking in the media has to do with the business model. Social media companies became the gatekeepers for traditional media about 20 years ago. Because negative emotions, like anger, fear and disgust, are the most powerfully reliable emotions to generate traffic, social media companies’ algorithms favor them.

Simple stories help drive traffic, too. People don’t like to read about rich people having problems and then making good; a corrupt wealthy person offers a simple answer for why you’re not wealthy, yourself: It’s because you’re virtuous! And God forbid we should ask ourselves a basic question about the Varsity Blues scandal: If I had $75,000, would I not have paid it to assure an easy path for my daughter in life? Can I honestly be sure, after the SAT tutor I paid for, the lessons, the recruiting web site for rowers, that I wouldn’t?

Social media and traditional media are filled with shallow and angry stories, offerings to the corporate gods that are as meaningless as the blood on the floor in a Roman arena.

A Flaw: Deriving Self-Worth From Others

Like many successful people, Caplan told me he derived his self-worth from other people’s opinions of him. In truth, he was groomed to become what he became, as a lot of white male leaders are today. A graduate of an elite school in Manhattan, he was an athlete in high school and college. A swimmer, he went to Cornell University. He graduated into the crappy economy of the late 80s and early 90s and went to law school to “kick the can down the road.”

But at Fordham, he told me, he kicked into gear instead. If you get into a second-tier law school you have to be at the absolute top of your class to be in the running for clerkships that set you on a path of success. So the competitive instincts that had been devoted to athletics shifted over to his career.

As an attorney, Caplan thought of himself as a pilot fish. “I took care of difficult situations for people,” he said. “I became so close to my clients, because that provided a constant reassurance that I was good enough.”

He was swimming in a pool that emphasizes size and appearance: He made his way up through the firm’s venture capital and private equity practices, helping some of the world’s richest people create some of the most ruthless companies. Private equity is a late-stage capitalistic community that never bears too close an inspection: The people all seem so, so nice, while they slice middle class lives down to size in the name of profits.

In Caplan’s family life, he was driven by the image of himself as a protector, he says now. “Have I done enough to make sure the people I care about are in the places they should be? If not, that’s a reflection of me.”

When he was a swimmer in high school and college, he was good at turns. Watching him over Zoom, watching him rub a deeply wrinkled forehead, I wondered if he would be able to make this redemptive turn.

When I was thinking about redemption narratives, I reached out to my writing group of novelists to ask them if they thought redemption had faded as a theme. No, they said. “I don't think redemption is ever old fashioned—I kind of feel like almost every book is about redemption in some form or the other,” said Priyanka Champaneri, author of City of Good Death, by email.

But two people in my broader circle of journalists and writers said they had recently canceled their New York Times subscriptions. “The opinion section was so mean-spirited,” said one. The mass media like the Times, they said, is different.

Because algorithms cannot love, or hope, or have faith, they cannot create or support the redemption stories we need.

Sideswipes

That Atlantic article also took a swipe at a nonprofit called Publicolor, where Caplan was on the board of directors. Publicolor was called “the world’s most quixotic nonprofit organization, … which seeks to “improve education in youth by promoting an imaginative use of color in school buildings.”

The founder, Ruth Lande Shuman, said she had written to the editor of The Atlantic in response to the story, but heard nothing. “The loss of accountability in social media has let loose the worst instincts,” she said. “There are people, maybe they’re insecure, who like to kick someone when they’re down.”

The idea behind Publicolor is that getting kids involved in projects like painting New York City public schools helps keep at-risk students in school. No, it’s not feeding starving children, but it seems like pretty good work. Shuman, who has a master’s in industrial design with a specialty in the psychological effects of color, founded the nonprofit in 1996. It directly serves 1,250 students a year, with a track record of helping 100% of them graduate on time and go on to post-secondary education, according to Publicolor. Of those, 135 are scholarship students, receiving from $2,500 to $7,000 each.

After his arrest, Caplan resigned from the board. But he kept volunteering one-on-one with the students, teaching financial literacy courses. Shuman asked Caplan to re-join the board of directors. “I was so proud of my board,” she said. “100% said absolutely bring him back on.”

People Who Have Hit Rough Patches

Caplan was in prison with nonviolent offenders, and those who were so old that they were no longer a threat.

“They were some of the best people I’ve ever met,” he said. You can think that sounds naïve, or you can remember the high-powered corporate world that Caplan emerged from, and the fact that he wasn’t in the main prison.

To Caplan, the lengths of time they were serving were unconscionable, and perhaps stupid. “There was one guy who had to be in his 70s. He had been there for 27 years. He told me his last arrest was for 2 grams of crack. He was half Native American and half African American.”

They called him OG, and he read novels.”

“He was so good natured,” Caplan said. “He just tried to cheer me up.”

Out of prison, Caplan incorporated prison reform, especially support for prisoners and their families, into the day-to-day work at Dutchess Management. He hired two of Publicolor’s alumni. And he hired, as an advisor, Bill Baroni, who had been deputy director of the Port Authority of New York and New Jersey. The U.S. Supreme Court dismissed his conviction for conspiracy and wire fraud for his role in the politically motivated closure of lanes on the George Washington Bridge, which resulted in traffic nightmares for commuters.

One of the reasons our prisons are such a mess is that very few people in positions of power have any kind of first-hand commitment to them. Caplan has begun to fill an unusual role: a power broker who just might actually care about the people in our society that hardly anybody else cares about.

The incarceration rate in the United States is about 810 people per 100,000. It’s up there with China, which imprisons a million Ugyhar Muslims, according to Pew Research. Compare that to the data of average peer nations, which is closer to 100 inmates per 100,000 adults. In 2020, Germany’s figure stood at 72 per 100,000, and France’s was 102 per 100,000, according to the World Prison Brief database.

Our incarceration rates started climbing in the 1970s and 80s, the decades when white power lashed out in response to the Civil Rights Movement of the 1960s. Incarceration rates are 5-7 times higher for Blacks than whites. By 2010, one-third of all Black male high-school dropouts under the age of 40 were in prison or jail, mostly for drug crimes – which in turn, are mostly economic crimes.

Here are three interesting facts I gleaned from a report issued in 2014 called The Growth of Incarceration in the United States: Exploring Causes and Consequences.

• Incarceration rates have little bearing on crime rates. During the 40 years the U.S. incarceration rate has been rising, the crime rate was up and down.

• The best evidence suggests black people use drugs at the same or lower rates than white people. But they are arrested and convicted at much higher rates, and sentenced to longer times.

• The drug economies took hold in the inner cities partly as a response to the decline of manufacturing in the middle of the 20^th century. Drug crimes are economic crimes.

Not A Glamorous Task

With the help and support of Caplan – the two men say they are close friends now — Baroni has become a go-to person, a connector, for people who are headed for prison and those coming out. He’s also teaching at Seton Hall’s law school, helping students understand the prison system. Dana Ball said he talks to Baroni at least once a month, conversations he found especially useful to understand the shifting rules of prison bureaucracy and house arrest during COVID.

Dutchess worked on the case of Kyle Kimoto, the Las Vegas man who had served 12 years of a 29-year sentence for a telemarketing scheme selling fake credit cards. Dutchess prepared briefing materials that helped propel Kimoto’s case to Donald Trump’s desk. Trump commuted the sentence. Caplan and Baroni also founded the Prison Visitation Fund to raise money so that people with relatives in prison can visit them.

Caplan has quietly immersed himself and donated tens of thousands of dollars to The Aleph Institute, the organization (that I started this story with) founded by rabbis that supports prisoners. He helps with strategy, budget and fundraising – he’s the go-to guy, Lipskar said.

During the evacuation of Afghan refugees, Aleph, via its work on international justice, was trying to help women judges escape the country. That’s when Lipskar reached out to Caplan, to ask him to help. Caplan raised $1 million for Aghan refugees, money that helped charter a plane to get 300 people out of the hands of the Taliban.

In April, a young orphan named Faizullah Abdalli wrote an op-ed in Canada’s The Globe and Mail under the headline, “I am an Aghan refugee, and I am daring to hope.” He was one of the refugees, and, from a refugee camp in the United Arab Emirates, he was planning to get an MBA. “I will do whatever I can to ensure I am one of those in a position to help shape a happier future for Afghanistan.”

‘Society Is Very Hard On People’

None of this work makes Caplan feel any better, he said. He’s been in therapy to understand more about what cracked inside him, that enabled him to make such a mistake. He has a clear sense that what he did wrong. “I was trying to take advantage of a system in a way that wasn’t fair,” he said.

Admitting the mistake, the fact that he paid a high price for his wrongdoing, his family’s support, the good works he’s done, and the new relationships he’s built – none of this makes him happy, he said. “I have enormous anxiety and enormous regret,” he said. “I have happy moments.”

As to why he talked to me – he’s given a handful of other interviews – he did it with reservations, but because he, too, believes that society is very hard on people. “Everybody makes mistakes,” he said. “Not everyone gets caught.”

Is Optimism Quaint?

McAdams, the Northwestern professor, believes we may be seeing a cultural shift around the question of redemption.

“Americans are more reluctant than they have been in the past to believe in or invest their emotion in positive stories of transformation,” he said. “Many redemptive stories are based on an assumption of hope for the future. … The “situation” may be a person’s life, a social problem, a societal challenge, or whatever.

“But that kind of optimism may be quaint in some circles. … Climate change, Covid, school shootings, political deadlock, Ukraine – well, this is not the most hopeful of times.”

We can only hope, together. “Redemption stories depend on (and sustain) hope,” McAdams wrote. “As hope wanes, we lose our faith in redemption.”

The Unfinished Tally

As for whether Gordon Caplan has redeemed himself – well, I don’t know if there’s a tally sheet for societal redemption. But passing the hat to save 300 Afghan refugees is a pretty big good deed; and paying for people to visit family members in prison seems like a pretty sincere one. You’ll have to decide for yourself what you think: It’s not easy to forgive someone like Caplan, if you’re like many of us, worrying about mortgages and rents. Then again, money is not everything: Ball, who has much less of it, seems a lot more comfortable with his life than Caplan does.

But you can’t deny he’s putting the work in, and the money. I hope he keeps going, and changing for the better. My mother used to say, “We’ve none of us gotten to zed, yet.” She gets wiser every year, even though she’s been gone for four.

In February, Caplan got his law license back, though returning to his former high-flying stature would be nearly impossible. He says he remains focused on his current work at Dutchess, helping his business and nonprofit clients “find success and value.” He may consider returning to law in the future.

“My validation now doesn’t come from success, but from helping others,” he said. “Hopefully that’s a different lens.”

Is he redeemed? “I’m not there. I’d like to get there.”

For now, that will have to do.