Winslow Williams was an illustrator of Yale programs in the 1950s. Williams was a graduate of the Yale Art School, class of 1941. A Virginia native, he has a style we really like. His first program was the Yale-Princeton cover seen below. His model for the Yale player kneeling is classmate Phil Crane (’41).

A description of the program cover says that the image was “prepared in oils, the first time such a medium has been used for a football program.” The Harvard-Yale program done in 1953 uses the same style as his original with a brilliant mix of the past looking at and co-mingling with the present.

His artwork for the Princeton-Yale program depicts the Yale trolley. It shows an unusually happy group of fans on their way to an early Yale game with an oversized mustached conductor. The original artwork was an oil painting which measured 26 inches x 34 inches. He spent two months researching costumes of the earlier period.

The Princeton-Yale program from 1952 is in the same style as his earlier works: