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Lieutenant Maddra was born and raised in Louisa County. He attended Louisa County Public Schools, graduating from Louisa County High School in 2004. With an early interest in pursuing a career in law enforcement, he attended Piedmont Virginia Community College where he obtained an AAS Degree majoring in Police Science, along with a Career Studies Certificate in Criminal Justice. He began his career with the University of Virginia Police Department in 2007 and attended the Central Shenandoah Criminal Justice Training Academy to obtain his law enforcement certification. During his time with UVA PD, he worked as a patrol officer and later, evidence technician. He joined the Louisa County Sheriff's Office in 2011 as a patrol deputy. While serving in the patrol division, he was promoted to the rank of Corporal and a few years later, to the rank of Sergeant. He later transferred to the Court Services Division and was promoted to the rank of Lieutenant in 2021.
During his career, Lieutenant Maddra was recognized by the Mother's Against Drunk Driving for most DUI arrests in a calendar year and was awarded the lifesaving award by both the University of Virginia Police Department and Louisa County Sheriff's Office. He has also obtained numerous law enforcement related certifications to include Certified Field Training Officer and graduate of First Line Supervisor School.