In the wake of her hit show Desperate Housewives, Felicity Huffman was making a name for herself off camera as a counter-intuitive D.G.A.F. (“Don’t Give a Fuck”) mom expert. Her vehicle was the Web site What the Flicka? (Flicka was Huffman’s nickname growing up), which she’d started in 2012, just after Desperate Housewives—for which she won an Emmy—went off the air. Huffman realized how many women out there sympathized with her character on the show, Lynette Scavo, a harried working mother. Why not cater to that crowd and give herself a new marketing platform, not to mention a place where she could vent and wax on about her own real-life parenting woes?

Huffman had always been open about how anxious she was as the parent of two girls, whom she’d had with her husband and fellow actor, William H. Macy. Both of their daughters were diagnosed early on with learning disabilities, which only fed her concern. As she would write in a legal document, “From the moment my children were born I worried that they got me as a Mother. I so desperately wanted to do it right and was so deathly afraid of doing it wrong. My own fears and lack of confidence, combined with a daughter who has learning disabilities often made me insecure and highly anxious from the beginning.”

Macy wrote to the judge in her case that his wife “has not carried being a mom easily. She’s struggled to find the balance between what the experts say and her common sense.”

Soccer mom, pre-soccer kid: Huffman and daughter Sophia, 2003.

Huffman and Macy’s eldest daughter, Sophia, in particular, caused concern. When Sophia was four, “she couldn’t even walk across a lawn in bare feet without flipping out,” Huffman wrote in her letter to the judge. “Tags in her shirt would cause a 20-minute meltdown. She didn’t know how to physically play with other kids, and most often she couldn’t sleep.”

Sophia was eventually diagnosed with sensory-modulation issues, meaning she either over- or under-responded to her environment and couldn’t regulate her emotions. After being tested by a neuropsychologist, she received accommodations at her schools.

A Housewife in Real Life

For Felicity Huffman, success was gradual. She starred in some Frasier episodes, and was cast on the acclaimed but short-lived Aaron Sorkin series Sports Night, on ABC. Then, in 2004, Desperate Housewives debuted, and everything changed. “I was shooting long hours, much more than thirty, forty hours a week,” she has said. “Then you’d have publicity on weekends. I never had a weekend off. Those were some very tense times, some real fun times.” But the flip side, she said, was that she was “drowning in motherhood.”

Indeed, every one of the film and TV projects she’d worked on since having children was fraught with “a lot of mommy guilt,” she said in an interview with the Television Academy. Filming Transamerica in 2004, for which Huffman received an Oscar nomination, meant flying to New York for a month of rehearsal and leaving her two children, who were under the age of four, at home. Her audition for Desperate Housewives had meant leaving the house at five o’clock in the afternoon while her daughters were in the bathtub. “I said, ‘I have to pull myself together,’” she said. “The kids are crying because I’m leaving.”

Her feelings seeped into the show’s writers’ room. “I think it was in Season Two, the scene where [Lynette] is on the soccer field after she’s been taking Ritalin to try and keep up with being a mother, keep up with kids. She has a breakdown, and she’s surrounded by her friends,” Huffman said. “She talks about, ‘I feel like a bad mother. I feel like my kids would be better off without me.’

“That all came from me. I was like, ‘This is what it feels like for me to be a mom. I feel sorry for my kids to have me as a mother.’”

On her Web site, Huffman played with this sentiment, turning self-pity into self-lacerating humor. “My first step in setting us free would be to make the phrase ‘Good Mother’ synonymous with ‘Mother Fucker,’ ” she wrote in June 2016. “Because that’s what we are doing to ourselves, and letting others do to us, being vicious and despicable. We are fucking ourselves.”

Huffman “has not carried being a mom easily,” reads a letter to a judge. “She’s struggled to find the balance between what the experts say and her common sense.”

She presented herself as a fellow survivor in the mothering game, an imperfect warrior willing to reveal her lapses and infractions, someone mothers everywhere could sit down with and wearily raise their glass of wine with, celebrating the act of just getting by. “If our kids are alive and decent citizens at 18,” she once posted, “we all deserve a fucking medal.”

Art imitating life: Huffman as Lynette Scavo in Desperate Housewives.

In another post, she admitted, “I have made so many mistakes as a parent it actually makes me nauseous to think about it.”

But however much she sold a WTF attitude toward mothering online, in real life she was hardly winging it. Macy has said that she constantly sought out parenting experts, both in friends whose children she admired and professionals. After reading the book The Blessing of a Skinned Knee, she tracked down its author, Wendy Mogel, and began consulting with her over the course of several years. And when Sophia enrolled at the Los Angeles County High School for the Arts (LACHSA), a public performing-arts school in downtown L.A., Huffman and Macy were highly visible and involved parents, using their clout to help fundraise for the school, which is tuition-free and depends on parental involvement. It also depends on donations, and Huffman and Macy gave $20,000 to the foundation that supports the school—other donors have included Frank Gehry and Paul Thomas Anderson, as well as Sony and Disney.

“I have made so many mistakes as a parent it actually makes me nauseous to think about it.”

Sophia Macy didn’t need to ride her parents’ coattails at LACHSA. A member of the school’s theater department, she landed many prominent roles in school productions, including the lead in Spring Awakening, and the role of Mary Jane in a one-act Spider-Man play. Students who knew her said who her parents were had nothing to do with her success; she had real talent. But to get her through the college-admissions process, her mother hired Rick Singer in the fall of 2016, when Sophia was a sophomore, after a friend told her he was the best college counselor in California.

Things started off with Singer as they always did. He hooked Sophia up with S.A.T. tutors and began helping her map out her college plan as he let it be known how well he understood college admissions. A year in, he had so won over Huffman that she entrusted him with the academic future of her younger daughter, Georgia, who was starting high school at Westridge School, a private all-girls school in Pasadena. He even met with administrators at Georgia’s school to advocate for an education program for her that took into account her learning disabilities.

He had become Huffman’s most trusted educational adviser.

The Rick Singer Way

Everything thrummed along smoothly for a year. Then, in August of 2017, Singer began to change his tune. In a meeting with Huffman, he said that Sophia really needed to improve her test scores. He was worried. He said she needed a math tutor to work with her twice a week. He also lectured Huffman on the dire state of college admissions, with all those legacies, athletes, and donors’ kids out there. He did not point out that Huffman and Macy were parents with pull: accomplished and famous thespians who volunteered their time and helped fundraise at their kids’ schools and presumably would do the same for any college their children attended. He did not remind them of their ability to make a donation to a college and turn their children into V.I.P. candidates.

Walk of shame, round two: Rick Singer leaves the federal courthouse in Boston after facing charges in the now infamous college-admissions cheating scheme, 2019.

All Huffman heard was Singer. And when he gave his doomsday speech, nothing else factored in. When he said that even if a school posted an admissions rate of 10 percent, for someone like Sophia it was more like 2 or 3 percent, Huffman went cold.

Sophia had her heart set on Juilliard, which doesn’t require standardized test scores, but Singer brushed this aside. Yes, her audition was important, he said, but her talent wouldn’t be enough, and other schools Sophia was interested in would need to see better test scores to even consider her. She would need, he said, between 1,250 and 1,350 out of 1,600 on the S.A.T.; without that score, Sophia would be rejected, no matter how good her audition was.

Having planted the seeds of dread and pushed them firmly down in the dirt, Singer then offered a solution. He said he had a way to “level the playing field.” Huffman, who was taking notes on her iPad during the meeting, began to type.

S.A.T. “Prep”

Four months later, Huffman was driving Sophia to West Hollywood College Preparatory School to take the S.A.T. Like most teenagers, Sophia was nervous about taking the test. She asked her mom if, after she was done, they could go out for ice cream.

Huffman tried to assure her daughter that everything would be fine, but her mind was elsewhere. As she steered the car down the winding canyon roads, she was plagued by the thought that she was doing something very wrong. Turn the car around, she told herself, according to a letter she wrote to the judge. Huffman drove on.

Waiting inside the school was Mark Riddell, an associate of Rick Singer’s who’d flown in from Tampa the night before to proctor Sophia’s test. He would receive $10,000 for the job. Sophia had no clue he was not a legitimate proctor and that, by the time she and her mother were having ice cream, he’d be correcting her answers and then handing the test over to Igor Dvorskiy, who would send it in to the College Board.

Turn the car around, she told herself, according to a letter she wrote to the judge. Huffman drove on.

Huffman was now formally entering into Singer’s side-door scheme—but only after months of deliberation. When Singer had first proposed cheating on the S.A.T., at a meeting at her home in August of 2017, Huffman had dutifully taken notes on what he said, but that was it. As he described how he could “level the playing field” for Sophia, Huffman typed into her laptop: “Control the outcome of the SAT—15 grand—get a proctor in the room with her and she gets the answer she needs to get. At the end of the test—the proctor is making sure. 75 grand—guy will make the scores perfect.”

Singer had assured Huffman that he had done this with many other families. He had also said that if Sophia’s scores went up too much—she’d already taken the P.S.A.T. and gotten around 1,000—it would arouse suspicion with the College Board. Huffman wrote: “If we start taking it multiple times—college board will only allow you a certain amount of increase—between tests—they would investigate you.”

When all was still well in the City of Angels: Huffman and Macy with daughters Sophia and Georgia at the Golden Globes, 2019.

Singer’s final point, one he insisted on, was that Sophia needed to get 100 percent extended time on the S.A.T. so that she could purportedly take it over two days at a site he controlled. Huffman would write to a judge that, after listening to Singer, “I was shocked that such a thing existed. And after he made the initial suggestion, it remained on the table. I couldn’t make up my mind for six weeks. I kept going back and forth while avoiding a final decision.”

As he described how he could “level the playing field” for Sophia, Huffman typed into her laptop: “Control the outcome of the SAT—15 grand—get a proctor in the room with her and she gets the answer she needs to get.”

Sophia had been seeing a neuropsychologist for her learning disabilities since she was eight and was re-tested every three years, as is recommended, in order to continue obtaining accommodations at school. In fact, Huffman had taken Sophia to be re-tested earlier that year, in June, and she had requalified for extra time. A few days after meeting with Singer, Huffman called up Sophia’s neuropsychologist and told the doctor to contact the College Board to make sure that Sophia would receive extended time on the S.A.T. She still wasn’t committed to Singer’s plan; she wanted to make sure Sophia had extra time on the test whether or not he was involved.

In fact, at that point, the only thing Huffman had agreed to do, based on Singer’s advice, was to hire a new math tutor for Sophia. “I honestly didn’t and don’t care about my daughter going to a prestigious college,” Huffman wrote in the judge’s letter of Sophia. “I just wanted to give her a shot at being considered for a program where her acting talent would be the deciding factor.... In my mind I knew that her success or failure in theater or film wouldn’t depend on her math skills. I didn’t want my daughter to be prevented from getting a shot at auditioning and doing what she loves because she can’t do math.” All she wanted to do, she said, was give her daughter “a fair shot.”

“If we start taking it multiple times—college board will only allow you a certain amount of increase—between tests—they would investigate you.”

In October, the College Board notified Sophia that she had been approved for 100 percent extra time on the S.A.T. Huffman forwarded the e-mail with this news to Singer and a counselor at LACHSA. “Hurray! She got it,” Huffman wrote.

When the high-school counselor wrote Huffman back, she said that Sophia could take the S.A.T. over two days in December at LACHSA and that the counselor would proctor the test. Huffman then forwarded that e-mail to Singer, adding, “Ruh Ro! Looks like LACHSA wants to provide own proctor.” Singer responded, “We will speak about it.”

Prison uniform, but make it classy.

According to her legal defense, Huffman was still confused as to what she should do. And so she called Singer up to discuss the options: Should Sophia take the test on her own with the extended time she’d been granted, or should he orchestrate things to ensure a good score? But there was no discussion to be had. The work Sophia had been doing on test prep wasn’t enough, Singer said, even with the extended time. She was going to be rejected by schools unless Huffman relied on him.

Later in the day, Singer e-mailed, asking: “Are we doing this on our own or with my help?”

“With your help,” Huffman replied.

Nicole LaPorte is the author of The Men Who Would Be King: An Almost Epic Tale of Moguls, Movies, and a Company Called DreamWorks