CHESAPEAKE, Va. - One day after announcing his impending retirement after 12 years as Chesapeake's sheriff, Jim O'Sullivan thanked a crowd of nearly 1,000 at an event Wednesday.
Watch: Chesapeake sheriff retires after 12 years in office
The Chesapeake Sheriff's Office held the second day of its annual Senior Support Services Seminar at the Chesapeake Conference Center. Chesapeake Mayor Rick West, State Sen. Louise Lucas (D-Chesapeake) and others offered their congratulations, before the sheriff took the mic.
"You have been a blessing to me," O'Sullivan told the crowd.
O'Sullivan, the city's third sheriff since its formation in the 1960s, says he will leave his seat on November 1 — with one year remaining in his term. Undersheriff David Rosado will take over for the remainder of the term, becoming Chesapeake's fourth sheriff.
After 33 years with the department, O'Sullivan tells News 3 he's ready for retirement, but says it's emotional thinking about the staff he's leaving behind.
"I always put them first and I know and appreciate them with all my heart and the only reason I am where I am is because of them," he said.
O'Sullivan named Rosado his heir apparent when he appointed him undersheriff in 2022, and Rosado spent the following years increasing his visibility in the community.
Watch: Chesapeake's new Undersheriff will be first Hispanic American in the role, tapped to be Sheriff's successor
The sheriff says that move was by design to ready his successor for the position. He did something similar as undersheriff to previous sheriff, John Newhart, who retired after four decades as sheriff in 2012.
“Working alongside a sheriff is invaluable and you don’t know what it’s like until the day you become the sheriff," said Sheriff O'Sullivan.
Rosado says he's taken a lot of the sheriff's work on since becoming undersheriff.
"Sheriff has allowed me to do the work as sheriff. He’s stepped back so I can step forward," Rosado told News 3.
It's a long list of responsibilities — including leading the office's 450-plus staff that operates the city's jail and guards the courts. The Chesapeake Sheriff's Office also has numerous partnerships with senior organizations, Special Olympics Virginia and city schools.
Watch: Chesapeake Sheriff's Office adds more School Resource Deputies to Chesapeake schools
“I know [Rosado] will do great things and I’m excited about that," said Sheriff O'Sullivan.
For now, the current sheriff says there are still 't's to be crossed and 'i's to be dotted. He continues to work toward a smooth transition, but tells News 3 he really wants to spend time with his staff.
“Just thank all our staff for everything they’ve done for me and everything they’ve done for the community," he said, adding that he's grateful to the community that's continued to elect him. “I’ll always be there for our people of Chesapeake. I love them dearly and I’m just thankful for the honor of being their sheriff.”
As for after November 1, he's looking forward to starting a new chapter...and just being called Jim.
“I’m getting married in November and I’ve always preferred being called Jim. I’m a boots on the ground type of person.”
