Born in Oneida County, New York, Wilson Shannon Bissell graduated from Yale in 1869. He was admitted to the New York Bar in 1871 and worked in the same law firm as Grover Cleveland in Buffalo. The two men became close friends and formed the law firm of Bass, Cleveland & Bissell in 1873.

After Cleveland’s election as governor of New York in 1882, Bissell reorganized his firm and remained in Buffalo as a prominent corporate attorney. Bissell served as an elector for his friend’s presidential campaign in 1884 but refused other appointments. When Cleveland was elected president for a second time in 1892, Bissell accepted the nomination for postmaster general (1893-1895). He struggled to implement civil service reforms while keeping Democratic stalwarts satisfied with political appointments within the postal service.

With his personal expenses mounting from living in Washington, D.C., Bissell resigned his post in 1895 and returned to Buffalo. He resumed his law career and became the chancellor of the University of Buffalo in 1902.