James S. Bayless' nature was reflected in his undergraduate years at Lehigh where he participated in everything from sports to student government to fraternities and social clubs. He helped organize many events, played the lead in the 1907 Mustard and Cheese musical, and also served as business manager for The Brown and White.
A mechanical engineering major, the Baltimore native held several engineering jobs after graduation, but spent most of his career in insurance underwriting, retiring as general manager of the Baltimore office of the Standard Accident Insurance Company in 1951. Bayless was an active member of the Lehigh Club of Maryland for many years, serving as its president in 1939. He was honored with the Alumni Association's highest honor, the Alumni Award, at his 45th reunion in 1953.
Many of his gifts to Lehigh were for financial aid. Before his death in 1965, he made a seed gift for the James S. '08 and Bertha T. Bayless Scholarship Fund, which gave preference to students from Baltimore interested in engineering. After his death, Mrs. Bayless, who had shared her husband's love for Lehigh, followed through on his wishes and completed the funding for the scholarship. In 1993, ten years after her death, Lehigh received a significant bequest from the estate.