On September 4, 2025, Charles County Circuit Court Judge Donine Carrington Martin sentenced Kenneth Tyrell Wade-Greene, a 35-year-old Waldorf resident, to 40 years in prison for a violent crime spree that included assaulting three police officers, attempting to rob a family at gunpoint, and possessing a firearm as a convicted felon. The sentencing follows Wade-Greene’s guilty plea on September 16, 2024, to three counts of second-degree assault, one count of attempted robbery, and one count of possession of a firearm with a felony conviction. Upon release, he faces five years of supervised probation, with an additional 20 years in prison if he violates probation terms.
The case stems from a series of events beginning on July 15, 2023, when Charles County Sheriff’s Office officers attempted to apprehend Wade-Greene, who was wanted by the St. Mary’s County Sheriff’s Office for armed carjacking, first-degree assault, and firearm-related charges. Spotted in a stolen vehicle in Waldorf, Wade-Greene fled, striking an officer with his vehicle during the pursuit. He evaded capture that day, setting the stage for further criminal activity.
Three days later, on July 18, 2023, officers observed Wade-Greene driving a Ford F-150 without a license plate near Young Road and Hunters Harbor Lane in Waldorf, a residential area known for its proximity to Thomas Stone High School and community parks. When police attempted to stop him, Wade-Greene abandoned the vehicle and fled on foot, drawing a black handgun from his waistband. His flight led him to a nearby residence, where he confronted two victims in their driveway, demanding their car keys at gunpoint. When they refused, he followed one victim into the home, pointing the firearm at him. The victim managed to lock himself in a room, prompting Wade-Greene to return outside.
Wade-Greene then rummaged through two vehicles in the driveway, searching for keys. He located keys to a Dodge Ram pickup truck inside the home and attempted to flee in it, still armed. The second victim intervened, struggling with Wade-Greene to prevent his escape. A responding officer arrived, ordering Wade-Greene to surrender, but he fled again, attempting to enter another residence through a locked garage door. During this chaos, he assaulted two additional officers before being taken into custody. A handgun, later determined not to belong to the residents, was found hidden in the garage freezer.
Assistant State’s Attorney John Stackhouse, prosecuting the case, requested a 50-year active sentence, citing Wade-Greene’s extensive criminal history dating back to 2010 and the terror he inflicted on a Waldorf family. Stackhouse highlighted the assault on three Charles County officers and the prior armed carjacking in St. Mary’s County, emphasizing the danger Wade-Greene posed to the community
Judge Martin imposed a total of 40 years: five years for one count of second-degree assault, 15 years for attempted robbery, 10 years for possession of a firearm with a felony conviction, and five years each for two additional counts of second-degree assault, all to be served consecutively. The sentence suspends portions of the terms for the assault and firearm charges, with 20 years held in reserve should Wade-Greene violate probation.
The department’s rapid response in this case prevented further harm, though the incident underscored the challenges of pursuing suspects across county lines, as Wade-Greene’s crimes spanned both Charles and St. Mary’s Counties. Sheriff Troy D. Berry has since advocated for enhanced regional cooperation to track wanted individuals.
This sentencing reflects Charles County’s commitment to holding violent offenders accountable, particularly those with prior felony convictions who continue to endanger public safety. State’s Attorney Tony Covington’s office has pursued aggressive prosecutions in similar cases, aiming to deter repeat offenders. Maryland law classifies second-degree assault as a misdemeanor punishable by up to seven years, while attempted robbery, a felony, carries a maximum of seven years. Possession of a firearm by a convicted felon, also a felony, can result in up to seven years, with enhanced penalties for repeat offenders. Wade-Greene’s prior convictions and the use of a firearm elevated the severity of his sentence.
The case has left a lasting impact on the Waldorf community, where residents value the area’s suburban charm and access to amenities like St. Charles Towne Center. The victims, whose quick thinking prevented a successful carjacking, demonstrated resilience, though the ordeal has heightened local awareness of safety concerns.
