McSherry was born in Frederick, Frederick County, Maryland to James McSherry, Jr. and Eliza Spurrier McSherry. He attended St. John's Literary Institute of Frederick from 1850 to 1856, and Mount Saint Mary's College from 1856 to 1861. He began the study of law in 1861, and was admitted to the Maryland Bar in 1864. In 1867, he was appointed a commissioner of the Frederick and Pennsylvania Line Railroad. He remained active in the management of the railroad up thru its demise in 1896.
During the American Civil War, McSherry was a Confederate sympathizer. He practiced law in Frederick, until he was appointed concurrently Chief Judge of the Frederick County Circuit Court (Sixth Judicial Circuit) and Associate Judge of the Maryland Court of Appeals in 1887. He was promoted to Chief Judge of the Court of Appeals in 1896, where he served until his death at his home in 1907.
While serving as Chief Judge, McSherry was a member of the Executive Committee of the State House Building Commission. The Committee oversaw the construction of the present day annex to the Maryland State House.
McSherry married Clara Louise McAleer on February 21, 1866, with whom he had one son and five daughters.
- Radoff, Morris L., The State House At Annapolis, The Hall of Records Commission - Department of General Services, State of Maryland, Annapolis 1972
- Biography from the Maryland Archives
- Herbermann, Charles, ed. (1913). Catholic Encyclopedia. New York: Robert Appleton Company. .
John Mitchell Robinson
| Chief Judge of the Maryland Court of Appeals
Andrew Hunter Boyd