Born on August 23, 1891, in Lexington, Virginia, Prettyman went to school in Washington, D.C. and Baltimore, Maryland.[4] He worked as an evenings and weekends sports correspondent for The Baltimore American, and a police reporter for The Baltimore Sun, from 1905 to 1907. He received a Bachelor of Arts degree in 1910 from Randolph–Macon College and an Artium Magister degree in 1911 from the same institution. He received a Bachelor of Laws in 1915 from Georgetown Law. He entered private practice in Hopewell, Virginia from 1915 to 1917.
Prettyman was a United States ArmyCaptain during World War I from 1917 to 1919. Although he was commissioned as an artillery captain, he also served as a judge advocate where he oversaw hundreds of courts-martial.[5] He was a special attorney for the Bureau of Internal Revenue of the United States Department of the Treasury in Washington, D.C., and New York City, New York from 1919 to 1920. He was in private practice in Chicago, Illinois, Washington, D.C., and New York City from 1920 to 1933.
Prettyman was general counsel for the Bureau of Internal Revenue from 1933 to 1934.[6] He was corporation counsel for Washington, D.C., from 1934 to 1936.[7] He was in private practice in Washington, D.C., and Hartford, Connecticut, from 1936 to 1945.[6] He was a professor of taxation at Georgetown from 1931 to 1946, and they awarded him an LLD in 1946. In 1961, both Randolph-Macon and the William Mitchell College of Law awarded him LLDs.[8]
Prettyman's service terminated on August 4, 1971, due to his death.[6] He was buried at Rockville Cemetery in Rockville, Maryland. He was survived by his wife and two children.[8]
^Joshua Kastenberg, To Raise and Discipline an Army: Major General Enoch Crowder, the Judge Advocate General's Office, and the Realignment of Civil and Military Relations in World War I. (DeKalb: Northern Illinois University Press, 2017), 128-129. He also protected several soldiers who were accused of subversion based on rumor and innuendo