Meet The Command Staff
Jim O'Sullivan
SHERIFF
heriff Jim O’Sullivan was born in 1966 in Montgomery County, Maryland and moved to the Hampton Roads area at the age of 1. He has resided in the City of Chesapeake since 1991. Sheriff O’Sullivan has three children (Dillon, Jake, and Kasey).
He began his law enforcement career in 1991 when he joined the Virginia Beach Sheriff’s Office before moving to the Chesapeake Sheriff’s Office in 1992. Since that time, Sheriff O’Sullivan has progressed through the ranks and on October 1, 2012, he was sworn in as the Sheriff of the City of Chesapeake. On November 5, 2013, Sheriff O’Sullivan was elected with 69% of the vote and won an uncontested race in 2017 and 2021 for his current 4 year term.
Sheriff O’Sullivan holds a Bachelor of Science Degree in Behavioral Science from Bluefield College in Bluefield, Virginia. Additionally, he graduated from the FBI Law Enforcement Executive Development School in 2010 and graduated from the prestigious FBI National Academy in 2012. Sheriff O’Sullivan is also a Certified Jail Manger through the American Jail Association. And he was unanimously voted in as the Interim Superintendent of the Hampton Roads Regional Jail in 2016.
During Sheriff O’Sullivan’s career, he has obtained a number of awards and honors. He served as the President for Section 6 of the FBI National Academy during the 248th session, received the Chief’s Recognition Award in 2011, and the Martin Luther King Leadership Award in 2010. He was awarded the City of Chesapeake’s – City Manager’s Award in 2009 for his leadership and fiscal responsibility in overseeing the sheriff’s office budget. During that period, the Sheriff was able to save over $1.1 million dollars. Additionally, Camelot Civic League of Chesapeake, Virginia recognized and honored him in 2013 as a “Community Trailblazer” and in 2014 as a “Points of Light” Appreciation Award recipient for providing outstanding community service to the citizens of Camelot. In 2015 The Virginia Athletic Council recognized and honored him for his community service involving children by presenting him the President’s Community Service Award. In 2016 Norfolk Alumni Chapter Kappa Alpha Psi Fraternity, Inc. awarded him with The 2016 Youth Service and Community Leadership Award for outstanding services and contributions to youth and the community. He was also awarded the 2016 Dr. James R. Jackson Public Service Award by the New Chesapeake Men for Progress for his community efforts and his involvement with youth to instill core values such as professionalism and leadership within them. In June of 2016 the Top Ladies of Distinction Hampton Roads Chapter presented him with the 2016 Ordinary Men on a Mission Award.
The Virginia Special Olympics inducted him into their Hall of Fame in July of 2016. In 2021 he was professionally certified by the Virginia Sheriff’s Institute
Sheriff O’Sullivan holds membership in a number of national, state, and local professional associations. He is currently a member of the Virginia State Sheriff’s Association, American Jail Association, American Correctional Association, and the National Sheriff’s Association. He serves on the Court Security, Transportation of Prisoners & Civil Process Committee for the National Sheriff’s Association. Locally, he is a member of the Chesapeake Fraternal Order of Police – Lodge #9 and the Chesapeake Law Enforcement Benevolent Association.
Sheriff O’Sullivan believes that community involvement and community service are of the utmost importance. He has served on various boards and actively participates to make Chesapeake a safer and better place to live. He has served on the Chesapeake Criminal Justice Services Board and the Chesapeake Community Services Board. He is the founder and Chairman of Children Today, Leaders Tomorrow which instills core community values in young women and men and gives them an opportunity to fulfill their potential in the future. Sheriff O’Sullivan serves as a board member for the Boys and Girls Club of Southeastern Virginia and the Urban League of Hampton Roads Inc. He is a member of the South Norfolk Ruritan Club, Public Arts Committee, the Chesapeake Sports Club, and TowneBank Board of Directors. In addition, Sheriff O’Sullivan is a past chairman for the Chesapeake Jubilee and a past chairman for the CHIP Health and Family Services Annual Duck Race. He has also volunteered his time coaching youth basketball and baseball for Chesapeake Parks and Recreation and the Southern Chesapeake Athletic Association. Sheriff O’Sullivan is a member of Hickory United Methodist Church in Southern Chesapeake.
David Rosado
UNDERSHERIFF
ndersheriff David Rosado is a 22-year veteran of the Chesapeake Sheriff’s Office. Born and raised in Brooklyn, New York; he moved to Chesapeake in 1999. While steadily rising through the ranks, Undersheriff Rosado served with distinction in corrections, support services, court services, administration, training, and public information. In June 2023, he graduated from the 286th Session of the FBI National Academy in Quantico. In 2022, Undersheriff Rosado made history as the city’s first Hispanic Undersheriff.
In 2015, the City of Chesapeake awarded Undersheriff Rosado a “Public Service Award” for his “Be a Buddy, Not a Bully” magic shows. Undersheriff Rosado used his sleight of hand and knowledge of interpersonal communication concepts to perform this educational, anti-bullying magic show to 32,000 students in Chesapeake Public Schools and the Hampton Roads area. In 2021, Undersheriff Rosado was awarded the “Award of Excellence” for his leadership through the COVID-19 pandemic. He is also the recipient of the Called Church’s “Martin Luther King Junior Leadership Award and a “Community Service Award.”
With a passion for community service, he considers it his mission to protect Chesapeake’s seniors and mentor its youth. In 2022, Sheriff O’Sullivan appointed Undersheriff Rosado as the head of the Senior Advocate” office—working with the Commonwealth’s Attorney to investigate crimes affecting seniors. Dedicated to supporting Special Olympics Virginia, Undersheriff helps coordinate the sheriff’s flagship Elite Unit program and Dancing with the Athletes. Undersheriff Rosado is also an active participant, speaker, and organizer in Sheriff O’Sullivan’s “ASPIRE” and “Children Today Leaders Tomorrow” non-profit leadership programs.
When Undersheriff Rosado is not working or volunteering, he enjoys spending time with his loving wife, Janet, and their two children, Ileana and Antonio. He has performed magic all around Virginia, North Carolina, and DC as “Magic Dave.” He says the joy and smiles on the faces of young and old alike are the ultimate rewards.
Christopher Pascal
CHIEF DEPUTY
t. Colonel Christopher Pascal is a 22-year veteran of the Chesapeake Sheriff’s Office. He was born and raised in Philadelphia, Pennsylvania, and moved to Chesapeake in 1998. As Chief Deputy, Lt. Colonel Pascal is responsible for overseeing operations of the Chesapeake Correctional Center and Court Services at the direction of the direction of the Sheriff and Undersheriff. He is a Certified Jail Manager (CJM) with the American Jail Association and holds a degree in criminal justice. Lt. Colonel Pascal graduated from the Virginia School of Polygraph in May 2011 and is a licensed polygraph examiner.
Passionate about community service, Lt. Colonel Pascal is an avid volunteer and fundraiser for Special Olympics Virginia. In 2013, he received the “Kenny Fields Unsung Hero Award” for his outstanding contributions to the non-profit organization. In 2017, he was inducted into “Law Enforcement Torch Run Hall of Fame.” He also serves as a board member on the Executive Council for the Law Enforcement Torch Run. In 2017, the Called Church presented him with the “Martin Luther King Jr. Leadership Award” for his dedication to community service.
Lt. Colonel Pascal is a General Instructor, Defensive Tactics Instructor, ASP Baton Instructor, and a LawFit Instructor. He takes pride in remaining as active as possible with our training academy.
First and foremost, to Lt. Colonel is his family: his wife (Nikki) and children (Christopher, Natalia, Michael, Kyler, and Sophia).
