- December 16, 2025
A 29-year veteran of the Flagler County Sheriff’s Office was appointed as chief deputy Monday morning by Sheriff Donald W. Fleming.
Maj. David O’Brien was moved to the rank of second in command and succeeds Rick Look in that post. Look, 63, is a 36-year law enforcement veteran who joined the Sheriff’s Office in 2005 as chief deputy. He served in that post until earlier this year when he left on disability leave from the agency.
In announcing O’Brien’s appointment before a packed room at the Operations Center in Bunnell, Fleming said he was looking for the new chief to continue the professional working relationship that he had built as a major with agency personnel.
“We need someone who can maintain consistency in operations in my absence," Fleming said. "I believe Chief O’Brien brings that to this post. He has shown he can take on added responsibility and he has done an excellent job."
O’Brien, 48, accepted the new responsibilities, saying he hoped to lean on the leadership skills that were provided to him as he rose through the agency’s ranks.
“I am confident that with the leadership that I’ve had, I will be able to provide as good an example as the one that was provided for me,” O’Brien said. “Under Sheriff Fleming’s leadership, we will continue to make Flagler County a safe place — one street, one neighborhood, and one community at a time.”
He began his law enforcement career in the Corrections Division when the Sheriff’s Office was housed in the old Flagler County Jail off State Road 100 in Bunnell. At that time, the Sheriff’s Administrative Offices shared space with the jail in the building that was constructed through the Works Progress Act in the mid-1940s.
From the Corrections Division, O’Brien transferred to the road patrol division. In 1991, he became the first full-time motorcycle deputy for the Sheriff’s Office.
O'Brien was promoted in 2001 to head up the first full-time Narcotics Investigation Division. He was promoted to captain and then major to lead the Criminal Investigation Division and later the Administrative Division before taking over the Operations Division.
He is a 2007 graduate of the FBI Academy in Quantico, Md.
