ELECTION 2022: St. Mary’s Sheriff candidate was disciplined in Garage Poker Series probe prior to retiring

LEONARDTOWN, MD. – Republican Sheriff hopeful Todd Fleenor’s last act in his twenty-two-year career as a St. Mary’s County Sheriff Deputy was to be disciplined in connection with the Garage Poker Series gambling operation conducted in Waldorf by St. Mary’s Orphans Court Judge Michael White and his son, Maryland State Police Lt. George White.

Fleenor and Deputy Stephen Simonds’s participation in the gambling operation was memorialized among the records of Woodville Pines LLC‘s multi-year gambling operation that featured both sports betting as well as year-long poker tournaments.

St. Mary’s Sheriff Tim Cameron said, in response to an inquiry by THE CHESAPEAKE TODAY, that he was not aware of the participation of the two in the operation or that they were using their government email addresses and ordered an investigation.

In response to a Public Information Act request, Sheriff Tim Cameron revealed that Todd Fleenor was the subject of an Administrative Investigation on February 23, 2022, and found to be in violation of a Policy on Internet Activities and Official Communications and was issued a written reprimand.  A second investigation into Conformance with Laws was determined by the Sheriff’s Department internal investigation conducted by Lt. Clay Safford, to be unfounded. According to the response, the same alleged violations against Stephen Simonds were judged to be unfounded and he remains on full duty.


In a response received on May 27, 2022, from Interim Assistant Sheriff David Yingling, the Sheriff’s Department email records and complete investigation were not available due to the investigation being conducted by another agency.

 The Sheriff’s Department was asked to identify the other agency and responded that they will do so upon the completion of the other agency’s investigation.

A Judicial Disabilities Commission investigation is set to hold hearings on June 10, 2022, into the financial activities of St. Mary’s Orphans Court Judge Michael White.

Lt. Clay Safford gave his pals a kiss by ignoring the below policy of the St. Mary’s Sheriff that prohibits illegal gambling.

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