Theodore Bennett, the Edgartown man who crashed his truck into the clothing store Third World Trading Co. and other property on Circuit Avenue in Oak Bluffs in November, appeared in the Edgartown District Court on Dec. 22 for a discovery compliance and jury election, where he was sentenced to 18 months of probation with a number of conditions.
Bennett, 43, was arraigned on Nov. 24 on charges including operating under the influence of alcohol, leaving the scene of property damage, negligent operation of a motor vehicle, and improper operation of a motor vehicle.
At the discovery compliance and jury election at the courthouse in late December, Bennett changed his plea to guilty, and his charge of improper operation of a motor vehicle was disposed of. He was sentenced to probation on the other three charges.
The crash occurred around 7:19 pm on Nov. 22 when Bennett drove his 2025 gray Toyota Tacoma into Third World Trading’s store front at 52 Circuit Ave., causing damage to the building’s front steps, front wall, large pane windows, merchandise inside the store, and a vehicle parked in the area, according to a police report from the incident.
It was also reported that Bennett struck a building on 145 Circuit Ave. earlier in the night, damaging the railing on a stairway at the front of the residence and causing damage to the lawn before fleeing the scene. According to the police report, Bennett subsequently drove northbound on Circuit Ave., a one-way street before crashing into Third World Trading.
No serious injuries were reported, but a resident in an upstairs apartment said the impact caused her to hit her head while showering.
According to the report, police found Bennett sitting alone in his truck with the engine running, smiling and uninjured. Bennett declined medical attention.
Bennett’s probation ends on June 21, and a restitution assessment hearing is scheduled for June 22 in the Edgartown District Courthouse to determine the final amount owed for property damage to the store, other structures, and vehicles.



