Major Caldwell Retires from Orange County Sheriff's Office for Second Time

Major David Caldwell is a lifelong resident of Orange County. He attended Chapel Hill High School and has been a prominent figure at the Orange County Sheriff’s Office since 1985.

After a long 40 years of service in the community Caldwell is ready to retire, but this isn’t the first time.

“Last time I think it took me 30 minutes to turn in my gear,” Caldwell said. “I think I’ve been doing it for about two weeks, a shirt here, a pair of pants there.”

Caldwell tried to retire back in 2008 but was eventually persuaded to return in 2016 at the sheriff’s request. Since then, he has been acting as the head of Support Services and Community Outreach.

Corporal Andre Richmond is school resource officer and has known Caldwell for 20 years. He said community involvement is extremely important for Caldwell – making this last position he held out of first retirement a perfect fit.

“You know he’s very involved in Chapel Hill communities and Orange County communities,” Richmond said. “Before he came back to the sheriff’s office he was working in Orange County and he helped develop a lot of the community centers – lot of your senior centers, especially in the black community. So, I think it was perfect timing.”

But before Caldwell came out of retirement to work as head of community outreach, he ran for the position of sheriff. A position that had him pitted against his childhood friend – current Orange County Sheriff Charles Blackwood.

“Lot of people say he and I ran against each other for the office, but we always say we never ran against each other we just ran for the same position,” Caldwell said. “We’ve been friends since junior high school.”

Caldwell said Sheriff Blackwood had to ask him three or four times to come back. Now that Caldwell is set to retire for the second time, Blackwood was the first to say goodbye. He was also the one chosen to present Caldwell with a plaque of appreciation.

“This is presented to Major David Caldwell Jr. in recognition and appreciation for 40 years of uncompromising commitment, dedication and law enforcement service to the citizens of Orange County this January 2020 from myself to you my brother,” Blackwood said.

While the sheriff’s office makes it clear that Caldwell cannot be ‘replaced,’ they do have another worthy Major to fill his role. Major Kevin Jones is a former patrol Lieutenant and has worked with the sheriff’s office for the past 22 years. He looks forward to the new role with knowledge that he will continue to learn under Caldwell’s guidance.

“I want to let him know how much I appreciate everything he has done for me,” Jones said. “I’ve known him since 1991 when I worked at a local grocery store close to his home. He’s one of the ones that got me interested in law enforcement. He was able to show me how to become a sharp deputy, how to speak with the people within the community and he’s just been a truly good leader. He’s always made it fun – every day you’d leave out laughing.”

As Major Caldwell gets ready to turn in the last of his uniform and wrap up his goodbyes, his last farewell is spoken to the community in which he has served for so long.

“Many people thank us for doing the job we do and I just want to thank them for allowing me to do it,” Caldwell said.

Major Caldwell Retires from Orange County Sheriff’s Office for Second Time

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