Winarsky received his B.A., M.S., and Ph.D. degrees in mathematics from the University of Chicago. He graduated summa cum laude and Phi Beta Kappa in 1969. Today, he volunteers as Chairman of the University of Chicago's Visiting Committee for the Physical Sciences Division. In 2011, Chicago recognized his service leadership with an Alumni Service Award. He was a National Science Foundation Fellow from 1969 until 1974, and an invited member of the mathematics department of the Institute for Advanced Study in Princeton, New Jersey. From 1974 to 1976, he was an Assistant Professor of Mathematics at the State University of New York (SUNY) at Albany.