Jennifer Levitz and Melissa Korn

Seventeen years before he pleaded guilty to running the nationwide college-admissions cheating scheme exposed by federal authorities last year in Operation Varsity Blues, William “Rick” Singer made a strong impression in Omaha, Neb., where he showed how far he was willing to go to propel a mediocre youth basketball team to victory.

Mr. Singer, who had already sold his first college-counseling business, was in Omaha in 2002 as part of a career detour into managing telephone call centers. When he arrived to take a job at the…

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