Calvin Ross, 42, of Waldorf
Calvin Ross, 42, of Waldorf, is facing 82 counts of violating a protective order following a series of alleged incidents in St. Mary’s County, according to court documents.
Ross was charged in two separate cases filed in the District Court for St. Mary’s County on April 23, 2026, and April 24, 2026. The charges stem from repeated allegations that he contacted or attempted to contact an adult female victim despite a court-issued protective order prohibiting any form of contact.
According to court records, the protective order was issued on March 30, 2026, and remains in effect through March 30, 2027. The order states that Ross is not permitted to contact the victim “in person, by telephone, in writing, or by any other means.”
Investigators with the St. Mary’s County Sheriff’s Office allege Ross violated that order repeatedly across multiple days in April 2026.
Court documents detail 13 specific violations tied to activity while Ross was incarcerated, including phone calls, electronic messages, and third-party contact attempts. These communications were made using jail telephone systems and a jail-issued tablet messaging system commonly referred to as “jail mail.”
According to the statement of probable cause, Ross contacted another individual by phone and “requested that they contact [the victim] to inform her he was charged… and that she needs to drop the protective order.” The call reportedly occurred shortly after Ross had been served with charging documents and reminded he was not to have any contact with the victim.
Investigators documented multiple messages sent through the jail-issued tablet system on April 23 and April 24, 2026, with specific timestamps for each message. Each communication was counted as a separate violation. The documents note that both the phone system and messaging system are assigned to individual incarcerated persons and require login credentials.
In a separate but related case, court records list 69 additional counts of violating the same protective order. While those charges do not detail the exact method of contact for each incident, they reference repeated violations occurring on multiple dates in April 2026.
A commitment document shows Ross was taken into custody on April 23, 2026, and ordered held at the St. Mary’s County Detention Center without bail. The document states he must not contact or harass the adult female victim and must comply with all conditions of the protective order.
A bail review was held on April 24, 2026, before Judge Karen Christy Holt Chesser. According to court records, Ross was ordered to be held without bond pending further proceedings.
