A Napa winemaker pays $50,000 to fly out a bogus test proctor to correct the answers on his daughter’s SATs. A Mill Valley investor pays $200,000 to get his son into USC as a football recruit — even though the teen’s high school doesn’t even have a football squad. A sailing coach accepts six-figure bribes to recruit a girl with minimal seafaring experience into Stanford.

The startling allegations were revealed Tuesday when federal prosecutors unsealed court documents implicating more than a dozen wealthy Bay Area parents as well as the sailing coach in a nationwide college-admissions cheating and bribery scheme. Federal officials allege the parents paid large sums of money to ensure their children got accepted to top colleges, including Stanford and Yale.

Details of the investigation, dubbed Operation Varsity Blues, raise new questions about admissions at the nation’s elite universities, a system advertised as fair but frequently criticized as being tipped in favor of the rich, and the integrity of collegiate sports programs.

The probe ensnared Hollywood actresses Felicity Huffman and Lori Loughlin, a long roster of college coaches and the alleged California-based ringleader, William Rick Singer, who ran the Edge College and Career Network and a charity called Key Worldwide Foundation. Singer’s outfit funneled money to coaches, school officials and bogus test proctors, prosecutors said.

“For every student admitted through fraud, an honest, genuinely talented student was rejected,” said Andrew Lelling, the U.S. attorney in Massachusetts. “We’re not talking about donating a building. We’re talking about deception and fraud.”

Singer, who lives in Sacramento and Newport Beach, was indicted on multiple counts of money laundering, racketeering, fraud and obstruction of justice, according to documents unsealed Tuesday. He pleaded guilty later in the day in a Boston courtroom and agreed to cooperate with investigators.

The federal complaint alleges that Stanford’s longtime sailing coach, John Nicholas Vandemoer, agreed in fall 2017 to designate the child of one of Singer’s clients as a recruit for the team in exchange for a payment to that program. Traditionally, university sports teams can set aside admissions spots for recruits, even if they are not awarded scholarships.

Vandemoer, 41, pleaded guilty Tuesday in Boston to one count of conspiracy to commit racketeering. In his plea agreement, prosecutors and his attorney agreed to recommend a prison sentence of 18 months. Stanford officials announced that Vandemoer had been fired.

“Stanford has been cooperating with the Department of Justice in its investigation and is deeply concerned by the allegations in this case,” school officials said in a statement. The university said it would investigate the matter but that federal officials had found no evidence implicating any other school employee.

The Stanford sailing program became embroiled in the scheme, prosecutors said, when Singer created a student-athlete application to the university that falsely claimed a young man was a competitive sailor.

By May 2018, the boy deferred his application to Stanford for a year, and Singer directed a $110,000 payment from one of his charity’s accounts to the Stanford sailing program in exchange for the coach’s agreement to designate the boy as a recruit the next year, prosecutors said.

Later that summer, the boy decided to attend a different university, but Vandemoer allegedly agreed with Singer to use that same recruiting spot for another of Singer’s clients in exchange for a $500,000 payment to the program.

Prosecutors said that’s when John B. Wilson, the founder and CEO of a private equity and real estate development firm in Massachusetts, sought the help of Singer to get his son to the University of Southern California as a water polo recruit and his two daughters to Stanford and Harvard.

Again, Singer and others created a college application for the new “recruit” that falsely indicated the teen was a competitive sailor, even though the student “had minimal sailing experience,” prosecutors said.

In a conversation recorded by federal officials, Singer allegedly explained to Wilson how the process would work: “I can send him your $500,000 that you wired into my account to secure the spot for one of your girls. I asked him for a second spot in sailing and he said he can’t do that because he has to actually recruit some real sailors so that Stanford doesn’t ... catch on.”

Wilson’s daughter also decided against attending Stanford, but Singer nonetheless paid the sailing program $160,000 from his charity, according to the criminal complaint. Singer and Vandemoer agreed that the payment would serve as a deposit for a future Singer recruit, officials said.

Vandemoer could not immediately be reached for comment, but his Boston-based attorney, Robert Fisher, said his client agreed to plead guilty on Tuesday because it was the “best course for him and his family, but also for Stanford.” The attorney said Vandemoer — Stanford’s coach for 11 years — did not pocket any of the money, which all went to the sailing program.

“He feels horrible about what happened,” Fisher said. “He’s very remorseful. At no point did he attempt to harm Stanford or the students at Stanford.”

Speaking a news conference, Lelling said the investigation caught 33 parents nationwide, exposing “a catalog of wealth and privilege.” The implicated universities were private schools Yale, Harvard, Stanford, USC, Wake Forest, Georgetown and the University of San Diego, along with public schools UCLA and the University of Texas in Austin.

Among those charged was Huffman, the Oscar-nominated actress who starred in “Desperate Housewives.” She and her spouse, actor William H. Macy — who was not charged for unexplained reasons — allegedly made payments to the bogus charity to facilitate cheating on their older daughter’s college entrance exams.

While working out the details of the alleged cheating scheme, Huffman allegedly wrote to Singer, “Ruh Ro! Looks like (my daughter’s high school) wants to provide own proctor.”

The wealthy parents from the Bay Area were accused of taking sometimes extravagant steps to get their children into colleges. Winemaker Agustin Huneeus Jr., of San Francisco, allegedly paid $50,000 for a proctor to be flown to the West Hollywood Test Center to correct his daughter’s SAT answers after she took the test. A psychologist’s note, coordinated through Singer, allowed her to take the test over multiple days, prosecutors said.

She wound up getting 1380 out of 1600, scoring in the 96th percentile nationally. However, authorities said, wiretapped phone calls indicate Huneeus complained to Singer’s group that his daughter’s scores were still not high enough.

Meanwhile, federal officials said, Huneeus agreed to pay $200,000 to get his daughter accepted to USC as a water polo recruit, despite having no experience in the sport. The money would allegedly be funneled to the school’s water polo coach, Jovan Vavic, and senior administrator Donna Heinel, who were also was charged in the case.

“You understand that (my daughter) is not worthy to be on that team,” Huneeus told Singer’s associates in a recorded phone call, according to a transcript included in court records. Huneeus then asked: “And is there a risk that this thing blows up in my face?”

William McGlashan Jr. of Mill Valley paid to get his son accepted as a USC football recruit, prosecutors said. The problem: He attended a high school with no football program, so they said he was a punter.

Ross residents Todd Blake, an entrepreneur and investor, and Diane Blake, an executive at a retail merchandising firm, are accused of bribing a USC athletic department official to get their daughter admitted as a volleyball recruit.

“So very excited that my daughter ... will be attending USC next year! #FightOn #trojanfamily,” Todd Blake wrote in a March 2018 Twitter post with a picture of a certificate of admissions to the university.

When the cooperating witness told Diane Blake that USC’s athletic records had been subpoenaed, she reportedly asked, “should I be concerned? I mean, (our daughter) doesn’t even know, you know?”

Bruce and Davina Isackson of Hillsborough allegedly paid $250,000 worth of Facebook shares for their daughter to be admitted to UCLA. Bruce Isackson is president of a real estate development firm in Woodside.

In some cases, parents spent as much as $6.5 million, prosecutors said, and Singer reportedly funneled more than $25 million through his bogus charity. Most of the students — none of whom were charged — continue to be enrolled at the colleges. The investigation is ongoing, Lelling said, and more arrests are possible.

San Francisco Chronicle staff writer Kimberly Veklerov contributed to this report.

Matthias Gafni and Evan Sernoffsky are San Francisco Chronicle staff writers. Email: matthias.gafni@sfchronicle.com, esernoffsky@sfchronicle.com Twitter: @mgafni @evansernoffsky