Sheriff Leonard serves over 400,000 citizens in Chesterfield, Virginia, with a professional force of over 320 employees with an annual budget more than $40 million.

His responsibilities primarily include the Security Division providing 24/7 security of 350+ inmates at the Chesterfield County Jail (additional 400+ inmates at Riverside Regional Jail), the Court Services Division which operates 17 courtrooms in Circuit, General District, and Juvenile and Domestic Relations Court which see over 500,000 people pass through every year, and Civil Process which handles nearly 90,000 papers annually.

Sheriff Leonard began his law enforcement career with the Richmond City Sheriff’s Office before moving over to the Chesterfield Police Department in 1982 when he became a patrolman. He rose through the ranks within the police department to the position of Major in command of all uniformed operations before his retirement in 2012 with 30 years of service where he served as Commander of the Uniform Operations Bureau, Commander of the Criminal Investigations Division, and Captain of Uniform Operations.  He also served as a Patrol Lieutenant, Sergeant, Detective, and Patrolman. Sheriff Leonard is qualified as an expert witness in the Use of Force, Accident Reconstruction and Polygraph.

In 2013, Sheriff Leonard began his career with the Chesterfield County Sheriff’s Office and on February 1, 2014, was appointed Sheriff by the Chief Circuit Court Judge of Chesterfield County. The citizens of Chesterfield County later elected Sheriff Karl S. Leonard during a special election and afterwards during a general election.

Sheriff Leonard received his bachelor’s degree in criminal justice from Buffalo State University and his master’s degree from Virginia Commonwealth University. He is a graduate of the FBI National Academy and the Senior Management Institute for Police at Suffolk (MA) University.

Sheriff Leonard is a past president of the Virginia Sheriff’s Institute, past State Chair for Special Olympics Virginia, and 2025 co-chair for the national Mobilize Recovery Campus Surge Program. He currently serves on many local and statewide Committees and Boards , to include the Legislative Committee for the Virginias Sheriff’s Association, Virginia State Recovery Court Executive Advisory Committee, State Offender Population Forecasting Policy Committee, Virginia Public Safety and Behavioral Health Committee, Opioid Abatement Civil Fine Disbursement Team, as group leader for the U.S. Attorney’s Office Central Virginia Overdose Working Group, Recovery Virginia Opioid Working Group, Central Virginia Law Enforcement Chief Executive Association, and the Chesterfield Colonial Heights Criminal Justice Board (Past Chair).

In 2021 Sheriff Leonard was awarded the international Leadership and Innovation Award by The Academy of Criminal Justice Services (ACJS). In 2024 he was awarded the Virginia Summer Institute for Addiction Studies Visionary Leadership Award.