Lawyer sentenced to one month in prison in college admissions cheating scandal

Boston, MA 10/3/19 Gordon Caplan leaves federal court after his sentencing in the college admissions scandal. Photo by Pat Greenhouse/Globe Staff Topic: 04caplan Reporter: Shelley Murphy
Pat Greenhouse/
Gordon Caplan left the federal court after his sentencing in the college admissions scandal.

A Connecticut attorney was sentenced to a month in prison Thursday for his role in the college admissions cheating scandal after telling a federal judge he had “lost sight of what it is to be a good father” when he paid a corrupt college counselor to rig his daughter’s ACT test score.

“I can barely face my daughter,” Gordon Caplan, 52, of Greenwich, Conn., said during his sentencing hearing in US District Court in Boston. “Shame and humiliation haunt me each and every second of every day.”

Judge Indira Talwani rejected a request for probation from Caplan’s lawyer, saying she wanted to send a message that would deter other parents from committing such a crime.


“How does someone get away with this without prison time?” said Talwani, who also ordered Caplan to pay a $50,000 fine and perform 250 hours of community service. He must report to prison on Nov. 6.

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Caplan, who was named “Dealmaker of the Year” by The American Lawyer magazine in 2018, resigned as cochairman of the international law firm Willkie Farr & Gallagher after his arrest in March and faces the possibility of disbarment.

He was among 52 people, including celebrities, coaches and high-powered financiers, charged in a brazen scheme in which wealthy parents allegedly paid bribes from $15,000 to $1.2 million to ringleader William “Rick” Singer to help their children get into top colleges. Singer has pleaded guilty to conspiracy to commit racketeering and money laundering and has cooperated with investigators.

In court Thursday, Caplan said he made “the worst decision of my life” when he paid Singer $75,000 to inflate his daughter’s ACT test score last December.

“Since my arrest, I’ve been consumed with why I engaged in this type of conduct,” Caplan said before a packed a courtroom, which included a dozen friends and relatives, including his wife and father. “I come to the painful realization that this whole episode was, at least in large part, my own ambition for my daughter going to college.”


Prosecutors recommended an eight-month sentence for Caplan, noting that in a July 2018 conversation that was secretly recorded by the FBI he told Singer, “to be honest, I’m not worried about the moral issue here.”

Caplan told Singer he was concerned only about whether his daughter, who was unaware he had rigged the test, could get caught cheating.

“Despite having the resources to provide his daughter with all legal means for success,” such as coaches and tutors, Assistant US Attorney Eric Rosen said, “Mr. Caplan insisted on buying her something that was not for sale: a near-perfect ACT score.”

At Singer’s direction, Caplan arranged for his daughter to fly to Los Angeles and meet with a psychologist who provided medical documentation that allowed her extra time to take the ACT. She took the test at a West Hollywood, Calif., test center, where Singer’s accomplice served as a proctor and corrected her answers after the test.

A month later, ACT notified Caplan’s daughter it had withdrawn its approval for her to take the test in California. Caplan hired a lawyer to challenge the refusal, forcing ACT to release her fraudulent score.


Caplan’s attorney, Joshua Levy, said other phone calls recorded by the FBI show that Caplan refused Singer’s offer to use “the side door,” a separate scheme in which parents paid to have their children falsely flagged as athletic recruits, helping them gain admittance into schools that included Yale University, Georgetown University, and the University of Southern California.

Caplan’s attorneys filed a 210-page sentencing memorandum that included more than five dozen letters from Caplan’s relatives and friends. They wrote that Caplan was “under family stress” when he met Singer and was desperate to help his daughter, who hoped to play tennis in college.

The letters portrayed Caplan, who also has a teenage son, as a dedicated father, lawyer and friend who had given generously to charitable causes and was ashamed of his lapse in judgment.

“My husband was wrong and he knows it,” Amy Caplan wrote to the judge. “His decision to immediately and publicly own his mistake came from his soul-crushing shame and remorse.”

Caplan’s lawyer asked the judge to consider that Caplan pleaded guilty to fraud charges only two months after his arrest and issued a public apology accepting responsibility for his actions.

Caplan is the fourth parent to be sentenced in the bribery scandal. Last month, actress Felicity Huffman was sentenced to 14 days in prison for paying Singer $15,000 to boost her daughter’s SAT scores. Two other parents were recently sentenced to four months in prison.

Outside the courthouse, Caplan addressed a throng of reporters and photographers.

“I am deeply and profoundly sorry for being involved in this mess,” he said. “I am focused now on giving everything I can to redeem some portion of my good name.”

Shelley Murphy can be reached at Follow her on Twitter @shelleymurph.