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Born in Havre de Grace and raised in Bel Air and Belcamp, Bob Cassilly attended Bel Air High School where he played varsity football and was a member of the orchestra. As an undergraduate at Johns Hopkins University, he wrestled and served in ROTC. An ROTC distinguished military graduate, Bob served five years in the active military as an Infantry officer, was awarded the coveted Ranger Tab, and continued his military service in the Army Reserves as a JAG and Civil Affairs officer. Bob graduated from the University of Baltimore Law School with honors and has been a member of the Maryland Bar since 1989. He has a law practice in Bel Air and has received numerous awards from the Maryland Bar Association for providing legal services to the disadvantaged.

Bob represented Harford County in the Maryland State Senate (District 34) from 2014 until his inauguration as County Executive in 2022. He has also served as Harford County Councilman for District C, Bel Air Mayor and Town Commissioner, and Chairman of the Republican Central Committee. His commitment to public service included three years in Iraq with the U.S. Army (101st and 82nd Divisions) and the State Department as part of the global war on terrorism, for which he was awarded the Bronze Star and the State Department’s Superior Honors Award, Meritorious Honors Award, and Expeditionary Service Award.