Orphans Court judges

Donna F. May and Billie J. Gilpin, are both Republicans and long time Judges of the three-member Allegany County Orphan's Court. May has held that elected office since 1986, for 24 years, while Gilpin has served as Judge for sixteen years. On November 2, 2010 both were re-elected to another four-year term of office. In the November 4, 2014 General Election, both Gilpin and May were re-elected to another four-year term as Judges of the Orphans' Court.

Billie Gilpin resigned from office in August 2017 for health reasons. In December 2017 Albert L. Feldstein was appointed by Maryland Governor Larry Hogan to fill the remainder of the term.

Donna May retired December 31, 2021. She was first elected in 1986 and re-elected eight times thereafter. With 35 years of service she is believed to be the longest serving Orphans’ Court Judge in the State of Maryland, one of the longest serving elected officials in Allegany County and one of the longest serving elected Republicans in the State of Maryland. Judge May frequently received the highest number of votes in recent election cycles.