Director
Name : William C. Bennett
Overview: Undersheriff William “Clayton” Bennett is a highly decorated law enforcement veteran and a native of Hampton Roads with a career spanning nearly four decades in the Chesapeake Sheriff’s Office. After joining as a Deputy Sheriff in 1982, he steadily rose through the ranks, culminating in his historic 2017 promotion to Undersheriff, becoming the first African-American to hold that position in the office’s history. Beyond his extensive professional achievements and certifications, Undersheriff Bennett is profoundly dedicated to community service, holding leadership positions on numerous boards, including as President of Project Lifesaver International and as a board member for The New Chesapeake Men for Progress. His deep commitment to Chesapeake is further evidenced by the many awards he has received for leadership and his volunteer work as a local youth sports coach.
Undersheriff William “Clayton” Bennett is a native of Hampton Roads. He has been a devoted law enforcement officer in Chesapeake for 39 years. He began his law enforcement career at the Chesapeake Sheriff’s Office in 1982 as a Deputy Sheriff and quickly rose up the ranks. Undersheriff Bennett served as the Chief of Corrections for 5 years and the Chief Deputy of Operations for 3 years, before being promoted to the rank of Lieutenant Colonel in 2014 and the rank of Undersheriff in 2017. He is the first African-American to achieve that rank in Chesapeake Sheriff’s Office history.
Undersheriff Bennett was born in the City of Norfolk and educated at Norfolk Catholic High School. He went on to earn a Bachelor’s Degree in Criminal Justice from Ohio Dominican University in Columbus, Ohio. Undersheriff Bennett is a Certified Jail Manager through the American Jail Association. He graduated with honors from the Virginia Beach Sheriff’s Office Law Enforcement Training Academy and from the Portsmouth Police Department’s SWAT and K-9 Patrol Academy. He served as a member of the Chesapeake Police Department’s SWAT team from 1983 to 1988.
Undersheriff Bennett has received a variety of awards and recognitions during his career including The New Chesapeake Men for Progress “Lifetime Achievement Award” in 2019, the City of Chesapeake’s “Innovation Award” in 2019, the New Journal and Guide “Impacting Lives Award” in 2017, The Exodus Faith Ministries “Martin Luther King Jr. Leadership Award” in 2015, the 2007 “Unsung Hero Award” named in Honor of Kenny Fields and the “2014 Hall of Fame Award” both from the Special Olympics Virginia Law Enforcement Torch Run. The Portsmouth-Suffolk Alumni Chapter Kappa Alpha Psi Fraternity Inc. “Community Service Award”, The New Chesapeake Men for Progress “Member of the Year Award”, and the Norfolk Alumni Chapter Kappa Alpha Psi Fraternity Inc. “Save Our Youth Foundation Inc. 2015-2017 Annual Black History Month Community Service Leadership Award.”
Undersheriff Bennett is the President of the “Project Lifesaver International” Board of Directors. He is the Vice-President of the “Children Today Leaders Tomorrow” Board and the “Charities Inc.” Board, a 501(c) (3) charitable organization that helps educate Chesapeake children and support residents and community projects. Undersheriff Bennett is on the board of “The New Chesapeake Men for Progress”, a non-profit group dedicated to improving the lives of local high school male students through scholarship opportunities. He is a member of the “Special Olympics Virginia” Board of Directors and has spearheaded several fundraisers including “Chesapeake Cycle Mania”, which raised more than $100,000 for Special Olympics in 2002. He was also a Director for the Chesapeake Law Enforcement Benevolent Association for approximately two years. Bennett is also a member of the Virginia Sheriff’s Association, the Fraternal Order of Police Lodge # 9, and the South Norfolk Ruritan Club.
Undersheriff Bennett is very involved in the community. He has volunteered as a coach for recreation football teams in Great Bridge and South Norfolk. When Undersheriff Bennett is not working or volunteering, he enjoys spending time with his wife of 38 years, Maria. He and Maria are extremely proud of their daughter Lisette, who is a University of Virginia graduate, and received her Master’s Degree from Longwood University. Her husband Cody, is a new member of the Chesapeake Sheriff’s Office.