Sheriff in Carroll, Maryland

2026 Primary Election

• Gail F. Wickless — Sheriff in Carroll, Maryland

  Gail F. Wickless is a Democratic candidate running for the office of Sheriff in Carroll County, Maryland. With a commitment to serving her community, Wickless aims to bring her unique perspective and leadership to the forefront of law enforcement in the county. Her campaign focuses on fostering trust and safety for all residents. As a member of the Democratic party, she is dedicated to upholding the values of justice and community engagement. Wickless seeks to address the needs of Carroll County through a proactive and inclusive approach to public safety, ensuring that the Sheriff's office is responsive and accountable to the people it serves.

• Jim DeWees — Sheriff in Carroll, Maryland

  Jim DeWees, a Republican, is the 58th Sheriff of Carroll County, Maryland, now in his third term since first being elected in 2014. A native of Carroll County, he is a 25-year veteran of the Maryland State Police, from which he retired as a Captain. His career included roles as a patrol trooper, supervisor, and commander. DeWees holds a Bachelor of Arts in Criminal Justice from Mount Saint Mary's University and a Master of Arts in Human Resource Development from Seton Hall University. As Sheriff, he leads a full-service law enforcement agency that includes road patrol, criminal investigations, a detention center, and courthouse security.

• Jay Landsman, Jr. — Sheriff in Carroll, Maryland

  Jay Landsman, Jr. is a Republican candidate for Carroll County Sheriff in the 2026 election. He is a law enforcement professional with over 30 years of experience, coming from a family with a multi-generational history of police service. His career began as a cadet in 1994, and he rose through the ranks of the Baltimore County Police Department to become the Colonel of the Operations Bureau. Landsman has held various roles, including patrol officer, detective, supervisor, and commander in units such as Burglary, Homicide/Missing Persons, and Vice/Narcotics. Following his tenure with Baltimore County, he served as the patrol commander and deputy chief of police at Towson University.