By Ernest Lowery
Special to the New Journal and Guide
Born in the historic, diverse Berkley section of Norfolk, Va., William Clayton Bennett, Jr. knew from an early age that he had a calling to serve the community. He and his family belonged to The Basilica of St. Mary of the Immaculate Conception in Norfolk. Living within a working-class area, having an active shipyard nearby, and hearing passing trains from Norfolk Southern rail system … his environment and observation of situations influenced his life’s mission for justice and equality.
In a remarkable unfolding of a 41-year law enforcement career from which he retired in October 2023, Col. Bennett’s proudest moment came when he was elevated to the position of Chesapeake’s Undersheriff, making history as the first African-American to attain this status in the Chesapeake Sheriff’s Office. What a tremendous example for youth to witness.
As a middle adolescent, he had considered being an attorney. As he moved towards college, he studied political science, then switched to studying criminal justice. He fondly remembered detective and action films he’d enjoyed as a youth, including “Shaft.” He later became more drawn towards police work, especially in response to some of his lived experiences.
While at a sizeable frat party in Columbus, Ohio, Bennett was singled out and harassed by a police officer. It was a crowded event with only a couple of Blacks present. Fortunately, it didn’t escalate but the difficulty of the raw first-hand personal experience left a strong impression on him. He soon became committed to being a law enforcement officer to help shape a better public understanding of the challenges for minorities in a culture that could be hostile.
During summer breaks from college, Bennett would come back to his family’s home in Chesapeake, Va., (nearby Norfolk) and work for the city’s sheriff’s department. They offered to hire him on full-time. After he applied for an open position in the Orange County, Florida Sheriff’s Office, he waited.
He received two calls on the same day responding to his applications for employment. During that time, he chose his hometown of Chesapeake, to pursue his career in public service and justice work.
Although Chesapeake didn’t offer the highest paid position at that time, it was worth it for him to remain in his hometown where he made a difference within the community. Bennett’s parents had lived in the Georgetown Colony of Chesapeake. His father was very connected to the community. It was not unusual for Mayor William (Bill) Ward and other respected community leaders to stop by for person-to-person interactions. At this point, the City of Chesapeake was about 30 years old and rapidly evolving. A culture was building.
Bennett’s first position was in the work-release program. His basic duties were to visit the inmates’ worksites, help them manage their monies – to pay child support and other court-imposed fines – and provide counseling. The goal was to prepare inmates with hope and accountability for returning to the outside world.
While having a college degree helped facilitate his new position, Clayton Bennett wanted to wear a uniform and work on the jail side where most of the inmates were. From there, after about six months, he was granted the move and a new experience on the main jail side.
As Bennett began to excel, he was recruited for the Policemen’s Academy; upon completion, he was called into the captain’s office unexpectedly where it went something like this …
The captain said, “I heard you like dogs.” Clayton replied, “Not really.”
The captain then said, “You start K-9 training in two weeks, Bennett.”
Bennett’s response: “Yes, sir!”
Chesapeake, being a young city, wanted educated, qualified minorities to round out key positions in the Sheriff’s Office. Bennett was the first African-American to hold a K-9 position. In time, this proved to be valuable training; his trusted dog became like his best friend. The two of them overcame some precarious situations together over the years.
It was through the K-9 experience that the team was recognized by the Chesapeake Police Department. At that time, Chesapeake police did not have a K-9 unit. Eventually, Bennett and his K-9 Brutus were integrated into the elite SWAT unit entry team (first to enter the building from a tactical viewpoint), leading to five years of extended training. Bennett proudly wore his SWAT team emblem. After many close encounters and receiving news that his wife was expecting their child, Bennett chose to move on from K-9 service.
Next on the agenda, as a senior deputy, Bennett ran classification, booking and transportation, which was called the support section. Deputy Bennett was instrumental in helping the Sheriff’s office get awarded the city’s first modern fingerprinting machine which accelerated the booking process in the department. It was important to maintain efficiency during booking. Computers were also being introduced at that time. Many changes were happening both with support equipment and personnel.
Senior Deputy Bennett recognized that women were more than capable of doing more tasks within the department, including transporting inmates. Men had dominated certain sections of the workforce prior to his integrating women into the fold.
One of Bennett’s pet peeves was that with all his experience, it took eight years to be promoted to Sergeant. He continued being innovative and working hard in classification; in a span of two years, he was promoted to Lieutenant. Bennett’s platoon command consisted of four Sergeants and about 38 deputies. On a regular basis, he would have pep talks during muster as needed to promote security concerns and the well-being/safety of the inmates. There were often cell searches and drills to be on the ready for any situation.
“It was important to keep morale up and impress upon the staff to stay alert at all times,” he said. He believed it was common sense.
At times, the platoon would come together at someone’s home for a spirit rally event which sometimes included a cook-out and chilling out together.
After being promoted Captain, he was later asked what that was like.
“It wasn’t a hard transition because I was already familiar with most of the policies, procedures and how to write a budget. Also, this came with more responsibility and personnel under my watch.” He was presented with two bars to acknowledge his promotion.
Captain Bennett was transferred from the jail side to the Court security division and Civil enforcement section. He was then responsible for those working with the court’s security and civil process.
In less than two years, Chesapeake Sheriff Jim Newhart appointed Bennett to Major; a significant achievement for him as well as the city of Chesapeake. This illustrates that the city was serious about qualified minorities having the opportunity to lead at one of its highest levels in law enforcement. He was later transferred back to the jail to manage its total operations.
This included Jail operations and Work release sections which consisted of three captains, 12 lieutenants, about 22 sergeants, plus all the staff in the correctional facility was under his command. He was responsible for about 250 of the 400 staff in the Sheriff’s Office. This required extensive knowledge of state and local regulations, such as audits and jail standards from the Board of Corrections.
It was at that time, Sheriff O’Sullivan appointed Bennett to the rank of Undersheriff. As next in line to the Sheriff, Bennett had oversight for all aspects of the Sheriff’s Office day-to-day operations.
During Colonel Bennett’s tenure, the Chesapeake City Jail was recognized as a model Jail facility throughout the state of Virginia.
When asked to reflect on his chosen career path, Colonel Bennett responded, “I knew I wanted to serve the community.”
That remained his guiding principle over time, as he brought honor, discipline, and dedicated public service to the arena of Chesapeake law enforcement. His dedication to public service and safety, made his city a safer area to work and live, while giving many of those serving time in the system hope and support for recovery to build better lives.
Join me in recognizing Undersheriff (Ret.) William Clayton Bennett, Jr. on his retirement as one of Chesapeake’s finest and most respected community public advocates in Hampton Roads!
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