CHESAPEAKE, Va. (WAVY) — Just a few pictures and certificates remain on display in the office Jim O’Sullivan has held for 12 years. Friday at 12:01 am he’s officially a civilian. The city of Chesapeake, which is just over 60 years old, has only had three Sheriffs.
“It feels great. I’ve always loved law enforcement since I was a child, and I never had dreams for being the sheriff. I always had dreams for helping the youth because I had so many people to help me growing up. And I’m single parent family and I feel what we have accomplished as a team together through children today, leaders tomorrow, with so many youth here in Chesapeake and also with helping our seniors and people that are disadvantaged,” O’Sullivan said.
His career includes service under the Virginia Beach sheriff where he worked in the jail. In 1992 he joined the Chesapeake Sheriff’s Office where he spent five years as a member of the Fugitive squad. He quickly rose to the top in administrative roles and in 2012 he was appointed interim Sheriff. Three campaigns later, O’Sullivan leaves with pride after creating what he says is a competitive pay plan,” O’Sullivan said.
You know, our numbers are generally very low with vacancies, and we’re very fortunate here that we have a public safety pay plan where people that we hire here can see where they’ll be in five years, ten years, 15 years down the road”O’Sullivan said.
“And they know that we’re they’ll be in a matrix as years go along. And that to me is so important because you have to take care of your employees. And it’s really one of the greatest things that I’ve done in my career is working on that for many years. And that’s why I stayed on for this term, is to make sure that I was kind of working with those that were the powers that be to have that come to fruition,”O’Sullivan said.
O’Sullivan named under sheriff Dave Rosado as the interim sheriff. Rosado has served the city for 23 years; his first run for the office will take place in November of 2025. O’Sullivan will soon open a Moyock, North Carolina-based construction company for residential and commercial properties.
