Gordon Caplan of Willkie Farr & Gallagher. Photo: Carmen Natale/ALM

When he first heard about it, Gordon Caplan said he thought a cheating conspiracy that would allow his daughter to have a high standardized score on a key college entrance exam “was a little weird.”

Caplan, a firm leader and top dealmaker at Willkie Farr & Gallagher, went forward anyway, paying $75,000 to a broker so his daughter’s answers on the standardized test could be corrected and then submitted, according to prosecutors’ court documents.

“I’m not worried about the moral issue here,” Caplan said, according to a wiretap transcript cited by federal prosecutors in Massachusetts. “I’m worried about the—if she’s caught doing that, you know, she’s finished.”

Caplan, who was arrested Tuesday, is one of dozens of people charged in an alleged nationwide conspiracy that facilitated cheating on college entrance exams and the admission of students to elite universities as purported athletic recruits.

The defendants include actresses, sports coaches, executives and businessmen. Of the approximately 50 defendants, Caplan stands out as co-chairman of an Am Law 50 law firm. He has practiced at Willkie for more than 16 years, according to his LinkedIn profile, and serves as a member of its executive committee.

Caplan, in the court documents, is described as an attorney and “co-chairman of an international law firm based in New York” who worked with participants of the scheme to ensure his daughter received a high enough ACT score for college admission. He is charged with conspiracy to commit mail and wire fraud.

Caplan has been released on a $500,000 bond. His attorney, Patrick Smith of New York criminal defense boutique Smith Villazor, did not return a message seeking comment. A person who answered Caplan’s phone number at his Willkie office said there was “no comment.” A firm spokeswoman did not immediately return a message seeking comment, neither did the firm’s chairman, Steven Gartner.

William Singer, the founder of a college preparatory business called the Edge College & Career Network, also known as The Key, is caught on several court-authorized wiretaps describing the cheating arrangement to Caplan.

For instance, in a June 2018 call, Singer said he used the scheme for about 800 other families and he tells Caplan, “What we do is we help the wealthiest families in the U.S. get their kids into school.”

He adds: “There is a front door which means you get in on your own. The back door is through institutional advancement, which is 10 times as much money. And I’ve created this side door in.”

Documents filed by prosecutors say Caplan participated in the scheme by making a donation of $75,000 to Key Worldwide Foundation, a purported charity. In exchange, Singer, who ultimately became a cooperating witness in the government’s case and who has agreed to plead guilty to his own role in the scheme, arranged for an associate to proctor Caplan’s daughter’s ACT exam. The proctor would then correct the answers after she had completed it.

In the wiretap transcript presented by prosecutors, Caplan asked how the arrangement worked. Singer tells Caplan: “So you come to my school, take the test on a Saturday. She’ll be in the room for six, six and a half hours taking this test. My proctor would then answer her questions, and by the end of the day, she would leave, and my proctor would make sure she would gets a score that would be equivalent to the number that we need to.”

Singer adds: “That’s how simple it is. She doesn’t know. Nobody knows what happens. It happened, she feels great about herself. She got a test a score, and now you’re actually capable for help getting into a school. Because the test score’s no longer an issue.”

In another phone call, Singer again explained to Caplan how the scheme worked, and in particular the need for Caplan’s daughter “to be stupid” when a psychologist evaluated her for learning disabilities in order to obtain the documentation to have extended time on the exam.

During the conversation, Caplan allegedly tells Singer that the arrangement “feels a little weird” but then asks him, “How do I get this done with you? What do I need to do?”

In another conversation, Caplan asked Singer, “if somebody catches this, what happens?” and he responds, “The only one who can catch it is if you guys tell somebody.”

Caplan, according to court documents, tells him, “I am not going to tell anybody.”

The ACT—at the request of law enforcement—ultimately granted a request for Caplan’s daughter to have extended time on the exam around Nov. 6, 2018, according to prosecutors. In a call two days later, Caplan asked Singer whether anyone involved in the cheating scheme had ever been caught.

“Keep in mind I am a lawyer. So I’m sort of rules-oriented,” Caplan says in the wiretap transcript. “Doing this with you, no way—she’s taking the test. It’s her taking the test, right? There’s no way …. any trouble comes out of this right?”

Caplan repeatedly asks Singer whether anyone had ever gotten in trouble for taking part in the scheme, noting that his spouse is “very nervous about a lot of this.” He says, “is there any way for this to get back to [my daughter] or to the family? I mean, this comes out—I—I don’t even want to know what you guys do.”

Singer, according to prosecutors, repeatedly sought to reassure Caplan that they had done this for others. He told Caplan, “So she’s going to take the test on her own, she’s going to do her best, all that stuff, and then we’re going to do our magic on the back end.”

According to prosecutors, Caplan and his daughter arrived at the test center in West Hollywood on Dec. 8, 2018, just after 7 a.m. Nearly five hours later, Caplan’s daughter left to meet her father and they drove away. About 12 days later, Caplan, who had already given $25,000, wired an additional $50,000 to Key Worldwide.