Caplan had been the co-chair of the international law firm Willkie Farr & Gallagher LLP. He had helped build up the firm's private equity practice. He was named 2018's "Dealmaker of the Year" by The American Lawyer, one of the top 50 merger and acquisition lawyers by the Global M&A Network, and a private equity MVP by Law360.
But in 2019, Caplan gained a different kind of fame when he was indicted in the "Varsity Blues" college admissions scandal.
"My persona was based on my career," Caplan told Law360 in an interview. "And losing that meant losing my persona. I was very proud of what I built and what I had done and accomplished and was always trying to do a bit more. And then, in a moment, it was gone. No one's fault but my own."
Caplan admitted he paid William "Rick" Singer, the mastermind of the scheme, $75,000 to have a test proctor change his daughter's ACT score. The scandal made national headlines, and its shame ran deep. Willkie cut ties with Caplan. He pled guilty to a single count of conspiracy to commit mail fraud and honest services mail fraud, served a one-month prison sentence and saw his law license suspended for two years. His fall was so sudden and so complete, he contemplated suicide.
"As soon as I was arrested, I knew my life had changed dramatically. And to be direct, for a good portion thereafter, I didn't think I would survive. I didn't think I wanted to survive, to live," Caplan said. "But once I decided to live, then it was about just moving forward through my own created, very difficult situation. That's what I've been doing since, one day at a time."
Now, nearly three years after his arrest, Caplan is trying to start over, with a new company and a law license newly reinstated by a New York appeals court.
Returning to a profitable law practice will be "not impossible, but difficult" for Caplan, according to Stephen Gillers, a New York University School of Law professor with expertise in legal ethics who has studied attorney disciplinary proceedings in New York.
The two-year suspension imposed on Caplan by a five-judge panel of the First Judicial Department was appropriate, Gillers said, because his crime concerned a personal matter and did not involve his work as an attorney, and because Caplan has paid the price for his crime in other ways.
"He has suffered a great deal as a result of what he did. He has a felony conviction. He is humiliated. He lost his perch at a major American law firm," Gillers said. "And it's almost certain that he will never have the same income from law practice that he had before all this happened."
But that is no longer the point for Caplan, who described starting over as "invigorating."
"It's not what I hoped for. It's not what I ever dreamed would be the case. It's not easy," he said. "But what I always loved about what I did was building, and now I'm building again in a different way."
For 18 months, he has been building up a strategic advisory business called Dutchess Management. The limited liability company, started in 1998 as a holding company for his family's investments, now has 10 employees from various phases of Caplan's life.
Two of its employees Caplan met during his longtime involvement with the New York nonprofit PubliColor, which offers after-school arts programming to middle and high school students who are at high risk for dropping out of their underperforming schools.
Dutchess' chief operating officer is Anna White, who worked with Caplan for years when she was the coordinator of Willkie Farr's private equity practice.
And then there is Bill Baroni, who serves as an adviser at Dutchess.
Baroni's résumé includes a stint at Blank Rome LLP, serving as a New Jersey state senator, and working as co-head of the Port Authority of New York and New Jersey. Baroni also served time in federal prison for his role in the George Washington Bridge lane closure scandal, known as Bridgegate, before the U.S. Supreme Court overturned his conviction. In a unanimous decision written by Justice Elena Kagan, the court found that because the lane closure that caused the gridlock was motivated by political retribution, not money or property, the fraud charges couldn't stick.
But Baroni had already spent three and a half months in prison by the time his conviction was overturned. He met Caplan in 2019, as he was preparing to serve out his sentence in the same facility in Pennsylvania where Baroni had been incarcerated.
"We were introduced because I wanted to know what it was like," Caplan said. "And right away, he came up and saw me and met with my family. And when I was inside, he kept in touch with my family every single day. And he's become an incredible partner and a very good friend."
Baroni echoed that sentiment, recalling the first time they spoke on the phone, late one Friday night, and feeling "from that first conversation that this was somebody whose contribution to criminal justice reform was going to be something he'd take seriously."
"I will take the people who have spent time in federal prison over most of the people I worked in politics with," Baroni said, adding that prisoners are more honest, more loyal, and have been through something "really hard."
"What I and Gordon and others have committed to is doing something with that experience to make positive change in the system," he said.
Baroni and Caplan have worked together on the Prison Visitation Fund, which gives money to family members to ameliorate the costs of visiting loved ones incarcerated in out-of-state federal prisons. They advocated for Kyle Kimoto, who was sentenced in 2008 to 29 years in federal prison for running a telemarketing company that had engaged in a deceptive credit card scheme. Then-President Donald Trump commuted his sentence in January 2021.
Dutchess Management has worked on prison condition and reentry projects as well, according to Caplan. He said Dutchess has advocated for getting people released from jail due to health issues at the height of the coronavirus, sought early release for people who were over-sentenced for drug or white collar crimes, helped the International Bar Association get people out of Afghanistan, and worked with the Aleph Institute, which helps people rebuild their lives after a conviction.
Dutchess also does traditional business advising work. Its LinkedIn page says it aided Hudson's Bay Co. and Insight Venture Partners — both former clients of Caplan from his Willkie days — on a stand-alone e-commerce company for Saks Off 5th.
"The team and I get deeply involved with businesses that are evolving or going through transitions and helping them get through it — through a lot of analysis, through negotiation, through some investing, through coordination and introducing them to other opportunities," Caplan said. "The world is going through an industrial revolution on steroids. Everything is being digitized, and COVID has only accelerated that. Traditional businesses that don't understand that and/or haven't been able to jump on that are left behind."
While Caplan doesn't yet know what his newly reinstated law license will mean for the scope of work that Dutchess does, he said he hopes to "prove worthy of it."
"Now I can use the legal part of my brain on problems again, and I hope to put it to good use," he said.
Caplan speaks of Dutchess' profitable work and its pro bono efforts as both being integral to the organization.
"I've built a small group of extremely bright, hardworking people who are focused on helping growing and evolving businesses get difficult things done, and at the same time, doing a tremendous amount of work to help people that could use our help that are not otherwise for profit," he said.
It's not unusual for people with past white collar convictions to return to their former careers with a new sense of purpose, according to Jeff Grant, an attorney and minister who runs the White Collar Support Group. The group boasts 450 members and holds weekly video chat meetings in a format not unlike that of Alcoholics Anonymous, with the serenity prayer, member testimonials and resource sharing. They discuss a topic each week, which might be something concrete, like the First Step Act, a 2018 federal law geared toward reentry after prison, or something more philosophical, like gratitude.
Nor is Caplan and Baroni's new focus on criminal justice reform unusual. Many members of the support group — which Grant says is diverse, but majority white, mostly male, and skews toward people in their 40s and 50s who were fairly successful — have emerged from their convictions and prison time with a transformative life experience and a fresh perspective.
"For Gordon or Bill or anyone from our support group who you would ask, there's just a new definition of success," Grant said. "I have more opportunities to have a profound place in the advancement of society. Some people don't have to go to prison to do that. But I did."
Grant was disbarred about 20 years ago for dipping into his clients' escrow accounts, then served a nearly 14-month federal prison sentence for applying for a fraudulent disaster-relief loan for his law office, falsely claiming it was impacted by the Sept. 11, 2001, terrorist attacks. His addiction to prescription opioids was in part to blame for "a waterfall of bad decisions," he said.
After prison, Grant went to divinity school. He started the support group a few years later, out of a concern that people with white collar convictions like his were "suffering in silence and isolation all over the country." The support group — which has always been virtual — took off during the pandemic, as video calls became the norm, and after the group was featured in the New Yorker.
"Prison is not the worst thing that can happen to you," Grant told Law360. "The worst thing that can happen to you is not having a comeback story."
Grant's law license was reinstated last year. His law firm's website mentions both his past opioid addiction and his federal prison sentence — hardly the typical fodder of an attorney bio. But Grant is interested in working with people in crisis, who are going through what he dealt with.
"There aren't many lawyers who will help someone prosecuted for white collar crime to navigate the system, and navigate their lives and their issues all the way through to a place years out where they have a chance of getting their life back or living a life that's joyous," he said. "Criminal defense lawyers, you usually don't see them again after sentencing."
Baroni would agree. In addition to working at Dutchess, he also teaches criminal law at Seton Hall University School of Law. He said that legal academia often focuses on investigation and prosecution — Fourth Amendment issues, trial practice — but not the "third phase" of criminal law, which he calls "jail to home."
"It's coming back to society, it's getting civil rights back, it's conditions of incarceration," he said. "There's an entire body of law there that even a number of criminal defense attorneys don't necessarily appreciate or focus on."
Caplan said in his former life as a corporate deal lawyer, he didn't give much thought to issues of incarceration. Now, he said, he's lived it. And while he had the resources and family support to navigate reentry, the difficulties of banking and getting insurance and starting a new career, he knows most people don't have the same resources he enjoys.
"I think the overwhelming majority of people in prison are there for basically drug offenses and-or relatively petty fraud offenses, and the sentencing at the federal and state level in this country is extremely punitive," he said. "And then the conditions in federal penitentiaries are not geared to success. They're geared to failure. Recidivism is extremely high. Being a felon — that's a life sentence. Even if you spend a month in jail, if you're a felon, you're a felon for life."
--Editing by Robert Rudinger and Jill Coffey.
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