(Bloomberg) -- On a phone call with the mastermind of the biggest college-admissions scam in U.S. history, Gordon Caplan asked what would happen if his daughter got caught cheating on her entrance exam.

“I’m not worried about the moral issues here,” Caplan, then co-chairman of the prestigious New York law firm Willkie Farr & Gallagher LLP, said with a laugh, according to an FBI transcript of the call. “I’m worried about the, if she’s caught doing that, you know, she’s finished.”

But it was Caplan, the American Lawyer’s Dealmaker of the Year in 2018, who got caught. Now, facing sentencing after admitting he paid $75,000 to fix his teenager’s test scores, he is asking for leniency. On Thursday afternoon, before U.S. District Judge Indira Talwani in Boston, he’ll find out if he gets it.

“The court is faced with the daunting task of deciding what additional punishment -- beyond his reputation, the fundamental breach of his daughter’s trust, his forfeited livelihood, and the destruction of his legal career -- is sufficient,” his lawyers wrote in a court filing.

Caplan, a graduate of Cornell University and Fordham University’s law school who specialized in mergers and acquisitions, pleaded guilty in May to a fraud-conspiracy charge. Acknowledging that Talwani, who has already sentenced two parents in the case to four-month prison terms, isn’t writing “on a clean slate,” he has asked for 14 days in jail, if he must be incarcerated. He noted that’s the sentence she gave the actor Felicity Huffman.

Read More: Huffman’s Jail Term Sends Signal to Other Parents in Scandal

Caplan’s lawyers blame the stress of his “family situation” and point to “the outsized role that money and special advantages already play” in college admissions.

“Gordon knows now that he allowed himself to fall prey to his own ego and ambitions for his children, confusing a desired result with what was best for his daughter,” they wrote in the filing to Talwani.

It was a fast, steep decline. When he rang in the new year, the Greenwich, Connecticut, lawyer was a star at Willkie, which ranks 50th on the American Lawyer’s 2019 list of the top 100 law firms. The ranking cited profit per equity partner of $3.1 million.

Prosecutors unveiled their case in early March. Three weeks later, Caplan announced he was pleading guilty, saying his daughter had been “devastated to learn what I did.” By then he had left the firm. In July, the Attorney Grievance Committee in New York imposed an interim suspension and will order full disciplinary action soon after his sentencing, his lawyers say.

They say he’s now “a broken man.”

Read More: Dad Blames College Con Man But Gets Jail for $400,000 Bribe

Caplan is one of 35 parents charged in the sprawling case, of whom 19 are fighting it out. Huffman was first to be sentenced, followed by two Los Angeles businessmen, who drew the four-month terms for paying hundreds of thousands of dollars to get their sons into elite schools, one as a bogus water polo recruit and the other as a fake tennis star.

Singer’s conversation with Caplan was one of many the ringleader covertly recorded as part of a deal with the government. He assured Caplan on the call that lots of wealthy families were using his services and, walking him through the racket, said his daughter would “be stupid” in a psychological evaluation in order to get a learning-disability designation. That way, she could take the exam over two days at a special center where Singer had placed one of his confederates.

Prosecutors say the moral indifference Caplan showed on that call, as well as his other words and deeds, call for eight months in prison.

“That a lawyer who has reached the apex of his profession could engage in such blatant criminality reveals a staggering disdain for the law,” Assistant U.S. Attorney Eric Rosen said in a court filing.

Read More: USC Emails Show Brazen Pay-to-Play Policy, Indicted Dad Says

In seeking leniency, Caplan cited a host of charitable acts, including working with underprivileged public school students, and donations of more than $500,000 each to Cornell and the School of Law at Fordham. More than 70 people wrote letters on his behalf.

Several of them, including the law school’s dean, Matthew Diller, said Caplan had led Willkie in representing, at no charge, Alma Kashkooli, a 12-year-old Iranian girl who was barred from entering the U.S. for lifesaving medical treatment in early 2017. She was allowed in and received the treatment.

“Mr. Caplan lifted burdens in the most difficult time of our life and when there was darkness he dared to be the first to shine the light,” Alma’s mother, Fahimeh Kashkooli, a law student at Fordham, wrote. “These are the qualities that I can define Mr. Caplan as a kind human being.”

The case is U.S. v. Abbott, 19-cr-10117, U.S. District Court, District of Massachusetts (Boston).

To contact the reporter on this story: Patricia Hurtado in Federal Court in Manhattan at pathurtado@bloomberg.net

To contact the editors responsible for this story: David Glovin at dglovin@bloomberg.net, Peter Jeffrey, Peter Blumberg

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