Father Simon Kenny was ordained on May 25, 1938. Kenny had various assignments, including serving as a chaplain in the United States Army during active-duty periods. After he retired from the Army, he became a pastor in Pylesville and was appointed Monsignor in 1982.
In 2016, a former parishioner reported that Kenny had forcefully French-kissed her without her consent in 1982 and then proceeded to do the same to her 16-year-old daughter. The incident caused immense shock and distress to the survivor and her family, leading them to stop attending church. In 2017, Archbishop Lori apologized to her, and the Archdiocese reported the incident to law enforcement and child protective services. Kenny died on July 2, 1999.
| Date | Church/Organization | Location |
| 1938-1943 | St. Mary’s Church | Hagerstown, MD |
| 1943-1946 | US Army Chaplain | — |
| 1946-1950 | St. Mary’s Church | Hagerstown, MD |
| 1950-1967 | US Army Chaplain | — |
| 1967-1968 | Holy Family Church | Randallstown, MD |
| 1967-1985 | St. Mary’s Church | Pylesville, MD |
