Winona Police Chief Chester Allan Brewer has filed a civil lawsuit in Shannon County, alleging he was unlawfully arrested by members of the Shannon County Sheriff’s Office earlier this year. The petition names Sheriff Steven Hogan, Deputies Kaleb Berkshire and Jacob Brixey, and the Shannon County Commission as defendants.
According to the filing, Brewer claims Berkshire and Brixey entered the Winona Police Department on February 27, 2026, and arrested him “without a warrant and without probable cause or justification” while acting under the color of their authority as county deputies. The petition further alleges the arrest was ordered by Sheriff Hogan and carried out as “a means of intimidation, revenge and humiliation.”
Brewer asserts the arrest was retaliation for several past incidents, including his participation in Hogan’s 2023 domestic assault arrest and his cooperation with multiple Missouri State Highway Patrol investigations into alleged misconduct within the sheriff’s office. The petition states Brewer suffered a cardiac event requiring hospitalization following the arrest, noting he was kept handcuffed during treatment “to further intimidate and humiliate Plaintiff.”
The lawsuit seeks damages for medical expenses—listed as $33,361.99—along with compensation for emotional distress, reputational harm, and attorney’s fees.
The defendants have not yet filed a response to the allegations. All claims in the petition represent the plaintiff’s assertions.
