Jennifer Levitz and Douglas Belkin:

One day in 2012, an admissions director at Occidental College got a surprising email. William “Rick” Singer proposed that the school reconsider an application from an academically challenged daughter of a wealthy family.

He wanted the school to overturn her rejection, and he suggested the parents would give the school money above and beyond tuition.

“Are you kidding?” an incredulous Mr. Singer wrote about her not being admitted. “We can create a win-win for both of us.”

Vince Cuseo, the admissions official at the small California liberal-arts school, gave a simple response: No.

Mr. Singer, the admitted mastermind of what federal prosecutors have called the largest admissions-cheating scandal in the country, had reason to be hopeful. He had made inroads into brand-name colleges and universities around the country scores of times, exploiting higher education’s focus on money and willingness to give extra consideration to wealthy applicants.