CHESAPEAKE, Va. - Major David Rosado has a way of connecting with people...whether it's with deputies assigned to the Chesapeake Jail or with civilians out in the community.
It's a talent that caught Sheriff Jim O'Sullivan's attention when Rosado first joined the Sheriff's Office in 2001. Both were in different roles at the time and then-"Major" O'Sullivan made Rosado the department's Public Information Officer.
From PIO...all the way to second-in-command.
“I’m going to promote him to my Undersheriff," O'Sullivan said in a recent interview with News 3.
The big date? October 4 — when Rosado will join others receiving promotions in the office.
It'll be the culmination of a 21-year career and for the Chesapeake Sheriff's Office, it'll be history. The 57-year-old will be the city's first Hispanic American Undersheriff.
"I'm very excited," he said.
But Rosado's story — and practice in communication — began much earlier, while growing up in the melting pot of New York City.
“(We were a) very close-knit Puerto Rican family, but we had friends from all different walks of life," Rosado recalls.
It's also where he started his "first" career.
"I worked in TV broadcast for ten years. I worked on the Geraldo Rivera show. I worked for Mr. Rivera for ten years, traveled with him and went to so many states, I can't even count. Also, abroad," said Rosado. "I think those skills I learned in broadcast, I was able to bring to the Sheriff's Office."
But when Rosado eventually followed his family to Hampton Roads, he says he didn't get right into law enforcement.
Without getting specific, he says he turned down a role as a studio camera operator at "one of the local news stations," before starting work as a personal trainer at a gym while also working security at one of the local malls.
By the time Rosado joined the Sheriff's Office, his experiences allowed for a quick rise through the ranks.
Now, as the new Undersheriff, his duties will expand even more: managing all the day-to-day operations of the office at the direction of Sheriff O'Sullivan. According to the Chesapeake Sheriff's Office, it includes 441 deputies and civilians working at the office, up to 1,000 inmates in the jail and all the people moving through Chesapeake courts — 357,000 last year alone.
And if that's not enough pressure, Sheriff O'Sullivan says Rosado is his choice to be the next Sheriff — just the fourth in Chesapeake's six-decade history as a city.
"This is going to be my last term," O'Sullivan told News 3. "I'm going to be mentoring him over the next two years and keeping him a lot closer to me to see my vision."
"If everything's going right, whenever that time is, I may leave before the end of the term."
The idea is Rosado would then finish out the term. But he would have to run and be voted in by Chesapeake voters in 2026.
All of this, while staring down all the challenges facing the Sheriff's Office, including the one Rosado believes is the biggest.
"I would say more than half of the residents in our jail have mental health issues we're not prepared for," he said. "We need more help."
Then, there are all the passion projects, like working with local youth and Special Olympics athletes in the Sheriff's Elite Unit. Rosado says he wants to put more focus on helping keep the city's elderly from becoming victims.
"With all the scams that are out there, they're being perpetrated or preyed upon," he told News 3.
It's a personal mission. Rosado's parents still live in Chesapeake and he says he still sees them multiple times a week. They will join his wife and kids at next week's promotion ceremony, which happens to fall in the middle of Hispanic Heritage Month
"I'm so proud of my dad and I would love for him to…I would love for him to see me in this position. He has dementia and it's hard," said Rosado, who added he still speaks Spanish with his parents.
It's a skill that's come in handy during his law enforcement career — "I was able to bridge that (language) gap with translations in the jail and sometimes in the court." — and one he believes will make a difference as he prepares to become an even bigger face for the Sheriff's Office.
Then there's the magic. Rosado has performed as a magician for decades at gigs outside his day job and for Sheriff's events. While with News 3, he unexpectedly lit his wallet on fire.
It's just one more way he's found a way to connect with others.
