Gordon Caplan is a former co-chairman of the international law firm Willkie Farr & Gallagher who pleaded guilty in 2019 to conspiracy to commit mail fraud for paying $75,000 to have his daughter’s ACT answers secretly corrected as part of the Operation Varsity Blues college admissions scandal. He served one month in federal prison, lost his partnership, had his New York law license suspended for two years, and has since built a strategic advisory firm and taken on criminal justice reform work.
The ACT Cheating Scheme
In 2018, Caplan contacted Rick Singer, the admissions consultant at the center of what the FBI later called Operation Varsity Blues. Singer ran a network that helped wealthy parents cheat on standardized tests and bribe college athletic coaches, moving payments through a sham charity called the Key Worldwide Foundation. Caplan paid Singer $75,000 to arrange for his daughter’s ACT to be taken at a testing center in West Hollywood, California, controlled by Singer’s associate Mark Riddell, who would correct her answers after she finished. Caplan’s daughter had previously scored a 22 out of 36; he told Singer he wanted a 32.1USA Today. College Admissions Scam Lawyer Gordon Caplan Faces Prison for Paying to Cheat on Test
The scheme required first obtaining extended testing time, based on a psychologist’s evaluation of learning differences. When the ACT initially denied the request, Caplan threatened to have lawyers challenge the decision.1USA Today. College Admissions Scam Lawyer Gordon Caplan Faces Prison for Paying to Cheat on Test Caplan has maintained that his daughter had no knowledge of the arrangement.
Federal prosecutors began intercepting phone calls between Caplan and Singer in June 2018 under a court-authorized wiretap, continuing through December.2Greenwich Time. Greenwich Lawyer Intends to Plead Guilty in College Admissions Scandal On one call, Singer called the plan the “home run of home runs” and said it “works every time,” and both men laughed. On another, Caplan said: “To be honest with you, I’m not worried about the moral issue here. I’m worried about the, if she’s caught doing that, you know, she’s finished.”1USA Today. College Admissions Scam Lawyer Gordon Caplan Faces Prison for Paying to Cheat on Test Singer also assured him that his daughter “won’t even know that it happened.” Prosecutors later used the recordings to argue that Caplan had actively sought Singer out and pushed the scheme forward at moments when he could have backed out.
Charges, Guilty Plea, and Sentence
Caplan was arrested on March 12, 2019, the day the Varsity Blues investigation was publicly unsealed in Boston.3Greenwich Time. Greenwich Lawyer Faces 8 to 14 Months in Prison He was charged in the U.S. District Court for the District of Massachusetts, case number 1:19-cr-10117, with one count of conspiracy to commit mail fraud and honest services mail fraud.4SEC. Administrative Proceeding File No. 3-19690 On April 5, 2019, he announced his intent to plead guilty, becoming one of the first parents to do so, saying through counsel that he took “full and sole responsibility” and was “deeply ashamed.”5CBS News. Gordon Caplan Guilty Plea in College Admissions Scandal He formally entered the plea on May 21, 2019.6U.S. Department of Justice. Fourth Parent Sentenced to Prison in College Admissions Case
On October 3, 2019, U.S. District Judge Indira Talwani sentenced Caplan, then 53, to one month in prison, one year of supervised release, 250 hours of community service, and a $50,000 fine.6U.S. Department of Justice. Fourth Parent Sentenced to Prison in College Admissions Case Prosecutors had recommended eight to 14 months.3Greenwich Time. Greenwich Lawyer Faces 8 to 14 Months in Prison Judge Talwani said Caplan had been an “active” participant who “chose instead to push ahead” when he could have walked away.1USA Today. College Admissions Scam Lawyer Gordon Caplan Faces Prison for Paying to Cheat on Test Caplan told the court: “I sincerely apologize to all students and families who are hurt by my conduct… I am deeply ashamed that I have in any way contributed to the broader concerns and cynicism in society that the system is rigged in favor of the rich.”7Forbes. The Redemption of Gordon Caplan
He reported to a federal prison camp in Loretto, Pennsylvania, on November 6, 2019, and completed roughly 28 days by December 2019.7Forbes. The Redemption of Gordon Caplan8Boston Globe. Prominent Conn. Lawyer Completes One-Month Prison Sentence in College Admissions Scandal While incarcerated, he taught business literacy and entrepreneurship to other inmates.9Leaders Magazine. Personal Growth and Positive Change
Caplan’s one-month term sat on the lower end of the Varsity Blues sentences, which ran from probation to 15 months for parents.10PBS NewsHour. Rick Singer, Mastermind of College Admissions Bribery Scandal, Set to Be Sentenced It matched the sentences Judge Talwani gave several other parents in the same period, including Robert Flaxman and Gregory and Marcia Abbott. Singer himself was sentenced in January 2023 to 42 months, the longest term in the case.11U.S. Department of Justice. Investigations of College Admissions and Testing Bribery Scheme
Loss of His Partnership and Law License
Caplan’s career at Willkie Farr & Gallagher collapsed within weeks of the arrest. Before the scandal he had chaired the firm’s venture capital practice, then its private equity practice, and had been co-chairman of the whole firm since 2015, overseeing roughly 1,000 attorneys across 13 offices.9Leaders Magazine. Personal Growth and Positive Change12Law360. After Varsity Blues Conviction, Gordon Caplan Starts Over The firm suspended him as co-chairman on March 13, 2019, one day after his arrest.13New York Times. Gordon Caplan, Lawyer, College Admissions Scandal On April 5, the day he announced his plea, Willkie confirmed he was “no longer a partner,” saying: “At Willkie, nothing is more important to us than our integrity and we do not tolerate behavior that runs contrary to our core values.”14Yahoo Finance. Ex-Willkie Co-Chair Gordon Caplan
On November 7, 2019, the New York Supreme Court, Appellate Division, placed Caplan on interim suspension. In a ruling dated February 18, 2021, the court converted it to a two-year suspension retroactive to November 2019. The court cited mitigating factors including his lack of prior discipline, his pro bono and charitable work, and what it called sincere remorse, describing the misconduct as an “aberration” but stressing that Caplan had “used his skills as a lawyer and the rewards of his successful law practice to circumvent the rules, not to honor them.”15FindLaw. In the Matter of Gordon R. Caplan He was reinstated to the New York bar by February 2022.16New York Law Journal. Ex-Willkie Co-Chairman Caplan Reinstated to Practicing Law After 2-Year Suspension
In February 2020, the Securities and Exchange Commission separately suspended Caplan from appearing or practicing before it under Rule 102(e)(2), citing his felony conviction and his New York bar suspension.4SEC. Administrative Proceeding File No. 3-19690
What Caplan Does Now
Since his release, Caplan has built up Dutchess Management LLC, a company he had originally incorporated in 1998 as a holding vehicle for family investments. Around 2020 he began turning it into a strategic advisory firm focused on corporate transformations, complex transactions, and philanthropic work.9Leaders Magazine. Personal Growth and Positive Change The firm notes on its website that it is not a law firm and does not provide legal services, and it has advised on deals including Kaseya’s $6.2 billion acquisition of Datto.17Dutchess Management. Dutchess Management Caplan reconnected with former Willkie Farr clients, advising Hudson’s Bay Co. and Insight Venture Partners on a stand-alone e-commerce company for Saks Off 5th.12Law360. After Varsity Blues Conviction, Gordon Caplan Starts Over He is the firm’s founder and CEO and sits on the boards of Usercentrics GmbH and Kubeshop.18Dutchess Management. Dutchess Management – Company Although his New York law license has been reinstated, he has continued to focus on Dutchess rather than returning to traditional legal practice.7Forbes. The Redemption of Gordon Caplan
Caplan has also taken on criminal justice reform work. He co-founded the Prison Visitation Fund with Bill Baroni, the former New Jersey state senator and Port Authority official whose Bridgegate conviction was unanimously overturned by the U.S. Supreme Court. The fund helps families who cannot afford to travel to visit relatives held in out-of-state federal prisons.19New Yorker. Life After White-Collar Crime Caplan and Baroni prepared briefing materials that contributed to President Donald Trump’s January 2021 commutation of Kyle Kimoto’s 29-year sentence for a telemarketing scheme.7Forbes. The Redemption of Gordon Caplan They have pushed for the release of inmates with health issues during COVID-19, sought early release for people they consider over-sentenced for drug or white-collar offenses, worked with the Aleph Institute on reentry support, and collaborated with the International Bar Association on evacuations from Afghanistan.12Law360. After Varsity Blues Conviction, Gordon Caplan Starts Over
In interviews, Caplan has called his conduct “wrong, stupid, inexcusable” and described his incarceration as “the most profound turning point in my life.” He told Leaders Magazine: “I’m not owed anything. I’ve never felt throughout this process that I deserve a second chance or any deep sense of redemption.”9Leaders Magazine. Personal Growth and Positive Change He remains based in Greenwich, Connecticut.