Estep Kyler, 69, of Chesapeake Beach
A Chesapeake Beach man is facing criminal charges following multiple incidents spanning December 2024 and January 2025. Estep Kyler, 69, of Chesapeake Beach, is charged in two separate cases with offenses including second-degree assault, malicious destruction of property, theft, stalking, and conspiracy to distribute a controlled dangerous substance (CDS).
According to court documents, Kyler is accused of slashing two car tires belonging to an adult female victim, allegedly causing damage valued at less than $1,000. This incident reportedly occurred on December 15, 2024, in Chesapeake Beach. The victim stated that Kyler had been following her and expressed fear for her safety.
On January 2, 2025, Kyler allegedly confronted the same victim again, resulting in charges of second-degree assault. The victim also accused Kyler of stealing $300 in cash from her vehicle during this encounter. The victim claimed Kyler spat on her, used profane language, and slammed her vehicle door before fleeing. She reported the incidents to authorities, who documented her injuries and recorded her account of the theft.
The victim further alleged that Kyler had been stalking her for months, prompting her to relocate. Court records show that she feared for her life and safety due to his persistent behavior. The stalking charge was filed alongside the theft and assault charges.
Separately, Kyler was arrested on January 3, 2025, after an undercover operation by the Calvert County Sheriff’s Office Drug Enforcement Unit. Detectives alleged that Kyler conspired to sell 15 Xanax pills (a Schedule IV CDS) to the same victim in exchange for $300. However, instead of providing the drugs, Kyler reportedly showed the victim Tylenol PM pills wrapped in cloth, took the cash, and attempted to leave without delivering the agreed-upon substances.
According to the probable cause statement, detectives witnessed the transaction through electronic surveillance and arrested Kyler shortly after the incident. A search of Kyler’s person reportedly revealed 13 Tylenol PM pills, $14 in cash, and other personal belongings.
Kyler now faces the following charges across both cases:
Malicious destruction of property (value under $1,000) – Misdemeanor.
Second-degree assault – Misdemeanor.
Theft: $100 to under $1,500 – Misdemeanor.
Stalking – Misdemeanor.
Conspiracy to distribute a controlled dangerous substance – Misdemeanor.
Estep Kyler, 69, of Chesapeake Beach
