Dover Man Sentenced to 95 Years in Stalking Case

Officials say the length of Caldwell’s sentencing was informed in part by his status as a habitual offender, for which he received an added 20 years of incarceration. Caldwell was previously charged in 2023 with first-degree assault. He also received the maximum penalty of 5 years on each of the 15 charges of breach of conditions during commitments.

 “The Defendant’s malicious, calculated, and horrifying acts placed his victim in a living nightmare and are a reminder of the fear that domestic violence survivors live with,” said Attorney General Kathy Jennings. “Our trial team, from prosecutors to police to social workers, did tremendous work in securing this sentence. I am grateful for them every day.”

In the early hours of Apr. 1, 2024, a Dover woman was staying at a friend’s house when Caldwell showed up and attempted to talk to her. When she refused, he tried to force his way into the home. When unsuccessful, Caldwell fired gunshots in the vicinity of the home and then drove away. On Aug. 13, 2024, Caldwell approached the same victim and her boyfriend at her home, proceeding to confront her boyfriend before eventually leaving. The next day, Caldwell, having planted a tracker on the victim’s car, followed the couple to a self-storage site in Dover, where he pulled a ski mask over his face and shot at them with a firearm before driving away. Caldwell was subsequently arrested on Aug. 15, 2024, after which he made numerous attempts to contact the victim from prison in violation of his orders not to do so.