The man in the center of the nationwide college admissions scandal could go to prison for 65 years and pay a fine of more than a $1 million.
Rick Singer, a former high school coach turned counselor, has pleaded guilty to masterminding what some estimate is a scheme that brought him $25 million.
Jon Reider, who worked in the Stanford admissions office for 15 years, knew that some parents tried to cross the line to get their kids into college.
"There is a very fine line — the law!" Reider said. "The law is very clear. This is fraud."
Some parents are accused of paying Singer to get their kids admission into colleges, or to cheat on ACT or SAT tests on behalf of their students.
"He had a big operation," Reider said. "He would give public talks at high schools, churches, synagogues, and he would make promises, and some of the promises involved Stanford."
Singer also co-wrote and published two books: one called "A Personal Brand is Essential to Gaining Admission to the College of Your Choice" and the other called "Getting In."
A 2014 Facebook post from an account that appears to belong to Singer shows clients he claimed to have helped included the late Apple CEO Steve Jobs, San Francisco 49ers legend Joe Montana and John Doerr, managing partner at Kleiner Perkins.
The post has not been verified by NBC Bay Area.
Montana tweeted out a response on Thursday, saying, "Mr. Singer's company provided nothing more than minimal consulting services to our family, like so many other families, with the college application process. Fortunately our kids were able to pick from a number of schools to attend due to their hard work and their merit."