Federal prosecutors pursuing the biggest university admissions fraud in U.S. history had a “raging debate” over whether to target the scheme’s mastermind or use him to go after the wealthy parents accused of buying their kids’ way into college.

In the end, Andrew Lelling, the former U.S. attorney for Massachusetts who oversaw the case, went big.

Lelling decided to cut a deal with William “Rick” Singer in exchange for his cooperation. That has resulted in almost three dozen parents — from former Pimco chief executive officer Douglas Hodge to actresses Lori Loughlin and Felicity Huffman — pleading guilty to spending tens or hundreds of thousands of dollars to get their kids into school with altered test scores or as phony athletes.

“It’s rare that you do a case that becomes part of the day-to-day conversation nationwide,” Lelling said in an interview, as the first of the parents stand trial in Boston. “It really penetrated the public’s awareness.”

The sprawling prosecution was splashed on the supermarket tabloids with the 2019 arrests of boldface names like Loughlin’s. Today, Lelling, who joined Jones Day as a partner this year, hopes the prospect of a perp walk and a prison jumpsuit will scare other parents straight.

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The U.S. charged 40 moms and dads across the country, from TV stars to financial power brokers, alleging they had schemed to get their kids into elite universities from Stanford to Harvard through bribes and other trickery. The crackdown has secured 33 guilty pleas from parents, with jail sentences ranging from two weeks for “Desperate Housewives” star Huffman to nine months for Hodge.

“It’s not about the amount of jail time — it was about the fact of jail time,” Lelling said, calling it a “leveler” and referring to “these famous or super-wealthy people putting on the same orange jumpsuit as the guy who robbed the bank or sold drugs.”

The defendants in the Boston trial, now in its third week, are former Wynn Resorts Ltd. executive Gamal Abdelaziz, accused of paying $300,000 in bribes to get his daughter into the University of Southern California as a basketball player, and private equity executive John B. Wilson, who allegedly paid $200,000 to win his son’s admission to USC as a water polo player and another $1 million to get his daughters into Stanford and Harvard as athletes. They say Singer duped them into believing they were just donating to the schools.

Four more parents are scheduled to go to trial early next year. None of the colleges or students swept up in the case have been charged.

Lelling, 51, is a parent himself, and was taking his daughter to look at colleges even as prosecutors in his office and federal agents were putting the massive case together. “That was a sort of a weird dissonance,” he said.

It began as just another white collar investigation, of a Los Angeles financier, Lelling recalled. Seeking leniency, the defendant tipped prosecutors and agents off about a Yale women’s soccer coach he said he had bribed to get his daughter into the Ivy League school. The coach would eventually lead them to Singer, who had promised parents a “bulletproof” way to get their kids into college by fixing their college board scores or turning them into phony athletic prospects.

“It was just one case among many,” Lelling said, but “once we began to learn about Singer, we began to realize the potential scope of this case, and it just grew and grew.” Ultimately he decided to strike a cooperation agreement with the corrupt admissions strategist, who the U.S. said had reaped $25 million from the racket. Under the deal, Singer agreed to secretly record conversations with the affluent parents he’d scooped up as clients.

Lelling has come in for some criticism of his decision to flip Singer against the parents — first-time, nonviolent offenders who couldn’t have engaged in the scheme without him. Nancy Gertner, a retired federal judge in Boston, finds it “troubling” that the government let the “ringleader” cooperate and went after the parents. The strategy, which Gertner called a waste of resources, may also mean a lesser sentence for Singer than for some of the parents, sending the wrong message to other con artists, she said.

“Are you trying to deter the parents who are taking advantage of what Singer has offered to them, or are you trying to deter the guy who really worked out the scheme from beginning to end?” said Gertner, a senior lecturer at Harvard Law School. “It’s like the major drug dealer who ends up rolling on the street dealers. The question is whether the deterrent value would have been better if they had gone to the mastermind of the scheme.”

Gertner acknowledges that the case got “major-league publicity.”

“If what Lelling is saying is ‘I got the biggest bang for the buck by indicting all of these very fancy people,’ I suppose that’s true,” she said. But if Singer avoids prison, she said, “it will mean that if you ensnare a rich enough person, a high-profile enough person, you can wind up dealing to get out of trouble if you name that person.”

Brad Bailey, a former federal prosecutor in Boston now in private practice, said it’s “unusual to take the mastermind of an alleged sophisticated fraud and give him sentencing concessions and go after people who are theoretically below him” in the hierarchy of wrongdoing. In this case, he said, prosecutors decided to signal that no one is above the law.

“Here the whole philosophy of the government’s case is just because you’re rich and allegedly powerful, we the government are not going to let you get away with this,” Bailey said. “In their opinion, the only way to go after the Lori Loughlins and Felicity Huffmans and all these well-known folks is to do it through a Rick Singer.”

Lelling defends his call and the greater impact he believes it’s had.

“There is a problem we sometimes run into in complex cases where, if you don’t use one of the key targets as a cooperator, the case you charge will be relatively small,” he said. “But if you do use them, it gives you the opportunity to charge a case that’s very large.”

The remote hearings forced by the pandemic made the impact on the public even greater, he added, citing Loughlin’s guilty plea by Zoom, to which Lelling said he realized some 500 people had logged on.

“There were people in bed, people walking their pets, people eating Doritos,” he said. “It was a slice of America, and they were all clicking in on Lori Loughlin’s plea hearing as if they’re watching regular TV. It was an easy way to see that the system works.”

Lelling is clear-eyed about the limits of his most famous case. He hasn’t removed the fundamental — and perfectly legal — advantages of wealth and privilege from the system, and overall he doesn’t think he’s changed what he sees as parents’ obsession with colleges as brands.

“There will be some trials, and then the case will eventually fade from people’s memory,” Lelling said. “So many upper- and middle-class parents are consumed by the name on the door. They really care whether it’s Cornell or Michigan or whatever, as if this is going to have a lasting impact on their child’s happiness and achievement. It’s just too bad that the system has gotten that far out of whack.”

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