Born in Baltimore, Maryland, Chesnut received an Artium Baccalaureus degree from Johns Hopkins University in 1892 and a Bachelor of Laws from the University of Maryland School of Law in 1894.

[1] Chesnut received a recess appointment from President Herbert Hoover on May 9, 1931, to a seat on the United States District Court for the District of Maryland vacated by Judge Morris Ames Soper.

He was nominated to the same position by President Hoover on December 15, 1931.

He was confirmed by the United States Senate on January 12, 1932, and received his commission the same day.

His service terminated on October 16, 1962, due to his death in Baltimore.