The Chesterfield County Sheriff’s Office marked a busy and meaningful season by recognizing staff achievements, supporting community initiatives, and advancing programs focused on service and rehabilitation.
On Thursday, December 11, volunteers with the Chesterfield Christmas Mother Program joined Sheriff Leonard and members of the Sheriff’s Office administration to recognize District Enhancement Deputies and their workforce crews for their tireless efforts in supporting this year’s mission. Their dedication played a vital role in ensuring the program’s success, and the Sheriff’s Office expressed appreciation for the continued partnership in serving the community.
Earlier in the month, members of the Sheriff’s Office joined personnel from the Chesterfield Police Department and Fire and EMS to support the RVA Polar Plunge, held Saturday, December 6, at Pocahontas State Park. Sheriff’s Office personnel assisted with event check-in and safety as part of a coordinated public safety effort. The annual event, hosted by Special Olympics of Virginia, raised approximately $70,000 in support of its athletes.
The Sheriff’s Office also announced several promotions, effective December 6, 2025. Lieutenant Robert Penepacker was promoted to Captain and assigned to Correctional Services. Sergeant William Wise was promoted to Lieutenant, also assigned to Correctional Services, and Deputy Amber Smith was promoted to Sergeant within Correctional Services. These promotions reflect the agency’s continued investment in leadership and professional growth.
Community partnership was further on display during the annual Christmas with a Cop event, hosted in collaboration with the Chesterfield Police Department and Chesterfield FOP Lodge 47. Held at the Walmart Supercenter on Iron Bridge Road, the event brought together law enforcement, members of the Board of Supervisors, and the Commonwealth’s Attorney’s Office to help children shop for clothing and toys made possible through generous community donations.
In support of successful re-entry efforts, the Sheriff’s Office also hosted a barber training program at the Chesterfield County Jail on December 1. Bruce Caskinette of Fine Line Barbershop provided professional barbering instruction to inmates, offering them a marketable skill they can carry with them upon release. Mr. Caskinette has also offered continued apprenticeship opportunities at his barbershop, and the Sheriff’s Office expressed sincere appreciation for his commitment to supporting individuals transitioning back into the community.
