PRINCE FREDERICK, Md. — A Sunderland man wanted for violating probation related to a prior assault and theft case is facing new charges after authorities say he fled from deputies during an attempted arrest in downtown Prince Frederick, triggering a foot pursuit through yards, streets and wooded terrain near Route 4.
Sherman Oswald Holland, 57, was spotted on May 26 by a deputy who recognized him from prior investigations and confirmed his identity using police database photos. Holland was reportedly walking near the intersection of Main Street and Hawk Hill Drive when he made eye contact with the deputy and was asked to step to the side of the road.
According to court records, the deputy informed Holland he was being placed under arrest and instructed him to put his hands behind his back. Holland initially complied, but as the deputy attempted to place him in handcuffs, he allegedly pulled away and sprinted down Main Street. The deputy gave chase on foot, repeatedly ordering Holland to stop. Holland reportedly ignored all commands and fled behind residential properties, through multiple yards and into a wooded area.
At one point, the pursuing deputy drew a department-issued Taser but did not deploy it due to an obstructed shot. Holland continued gaining distance, running across several properties along Wilson Court before disappearing into a heavily wooded area adjacent to Route 4. Deputies then deployed K-9 units and drone surveillance in an attempt to track Holland’s location, but the efforts were ultimately unsuccessful. He was last seen emerging from the woods and walking back toward Main Street.
Investigators noted Holland was already a suspect in several recent vehicle tampering incidents in the Prince Frederick area at the time of the encounter.
He was formally charged with resisting arrest, obstructing and hindering, and failure to obey a lawful order. Under Maryland law, each charge is classified as a misdemeanor and may carry a maximum sentence of up to three years in jail if served consecutively.
An arrest warrant was issued by Judge Louis Oertly the same day. Holland was apprehended two days later and held without bond. At a hearing on May 29, Judge Michelle R. Saunders upheld the no-bond status. Holland is currently represented by the Office of the Public Defender, and his case is set for trial on July 22 in Calvert County District Court.
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