By james art 
CHESAPEAKE, Va. – 23 years after starting as a deputy in the Chesapeake Sheriff’s Office, Dave Rosado was named the city’s fourth sheriff on Friday.
Rosado succeeds Jim O’Sullivan, who spent 12 years leading the office, which serves the city’s jail and court. Considering retirement, O’Sullivan promoted Rosado to deputy sheriff in 2022 with the intention of eventually elevating him to the top job.
Rosado, 59, says he has taken on the many responsibilities of a “sheriff” in anticipation of the promotion. On Friday, O’Sullivan officially presented the badge and title.
“‘Sheriff Dave Rosado.’ It’s a little surreal, but I’m up for the challenge,” the new sheriff told News 3.
Lydia Johnson/WTKR
It’s surreal … and probably not the job Rosado envisioned at the start of his pro career.
Raised by Puerto Rican Americans in New York, Rosado began a career in radio and worked closely with journalist Geraldo Rivera for a long time.
He says he moved to Hampton Roads in the late 1990s and quit a professional camera job at a local TV station because of low pay. In 2001, Rosado followed a friend to the Chesapeake Sheriff’s Office.
“I worked in the back of the prison. I worked on the reservations,” he said of his early jobs as a deputy.
Working his way up, Rosado spent time as a public information officer and would continue his visibility through the sheriff’s Special Olympics and senior programs. He insists those programs will continue to be emphasized as he moves to the top job.
He also wants to increase the focus on the mental health of inmates at Chesapeake Prison.
“Nearly half of our inmates have mental health issues, so we want to have a solution for them. Right now as we speak we are building a mental health treatment unit in our jail and that will house and help these inmates,” Sheriff Rosado told News 3.
Another goal is to further expand a program that places deputies in Chesapeake Public Schools as school resource officers.
Lydia Johnson/WTKR
That work will happen as Rosado campaigns to keep his new job.
Sheriff is an elected position, and Rosado is finishing the last year of O’Sullivan’s term. A judge waived the need for a special election this year, but Rosado will have to run for re-election in 2025.
That means balancing the sheriff’s duties with the campaign. Rosado insists that won’t be a problem.
“I learned how to serve from my parents,” he told News 3.
Rosado’s mother was in the audience at the swearing-in ceremony, along with his wife and children. Missing is his father, who Rosado says died last year.
It’s an emotional moment for the new sheriff, but he says the lessons from his father live on.
Rosado is the first Hispanic to serve as Sheriff of Chesapeake and believes his upbringing will help him better serve.
“As a deputy, I was interpreting for Spanish-speaking inmates and it was hard for them to communicate, so I bridged that gap,” he said. “Being a Puerto Rican coming from a different background, I can use that experience to relate and it’s about connecting with our citizens.”
The Chesapeake Sheriff’s Office has a staff of about 450. J. Arthur Hodges was the town of Chesapeake’s first sheriff, followed by John Newhart, who held the position for 42 years. Jim O’Sullivan served in early 2012.