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A Rape Allegation at Heart of Divorce Between Palm Coast Mayor Milissa Holland And Sheriff’s Ex-Chief Deputy

| July 10, 2017

Palm Coast Mayor Milissa Holland in court filings alleges ex-Flagler Sheriff Chief Deputy David O’Brien repeatedly raped her while she was unconscious in 2013, shortly before their separation.

Commissioner to Lobbyist: Milissa Holland Joins Powerful Southern Strategy Group

| July 17, 2013

In a pair of candid interviews, former Flagler County Commissioner Milissa Holland traced her personal and professional trajectories that took her from representing taxpayers in government to representing the special-interest clients of the Southern Strategy Group, one of Florida’s–and the nation’s–most powerful lobbying firms.

“Rising Star” Paul Bovino Is Appointed Commander of Flagler Sheriff’s Patrol Division

| March 20, 2013

Paul Bovino was appointed permanent commander of the Neighborhood Services Division, formerly known as the patrol division, in place of David O’Brien, who was given the choice of either being fired or retiring in the messy culmination of a re-organization that had initially cast O’Brien among the management team.

Back from a Limb, Ray Stevens “Distances” Himself from November’s Manfre Endorsement

| March 14, 2013

Republican Ray Stevens says he would not have endorsed Democrat Jim Manfre in November had he known that firings were on the way. Manfre himself defended his actions as necessary, while thanking Stevens for his opinions.

Sheriff’s Ex-PIO Files Sex Discrimination Grievance Over 35% Pay Cut and Demotion

| March 7, 2013

Sheriff Manfre had hired Debra Johnson as his public information officer in 2001, only to demote her to assistant PIO and cut her pay in January, triggering one in a series of grievances in a mounting backlash against the new sheriff’s aggressive remaking of the agency.

Sheriff Manfre Fires David O’Brien 2 Months After Short-Listing Him for Undersheriff

| March 6, 2013

The latest of numerous shocks to roil the Flagler County Sheriff’s Office in the last two months was also a stunning turnaround for O’Brien, 49, who was appointed Manfre’s chief deputy during Manfre’s first tenure as Flagler County Sheriff a decade ago.

Flagler Schools Considering Public Color-Coded Emergency System to Signal Lockdowns

| December 21, 2012

Before the Newtown massacre but after a close call with a student who threatened to attack a school last week, Flagler school and sheriff’s officials met to devise a system that would let people know in real time when a school, college or day care center was in lockdown.

Manfre Picks Rick Staly as Undersheriff, Passing Over O’Brien, Who’ll Be Chief Deputy

| December 3, 2012

Incoming Flagler County Sheriff Jim Manfre’s appointment of Rick Staly as undersheriff signals Manfre’s intent to shake up the internal workings of the agency while maintaining some continuity with O’Brien, who’d risen to chief deputy during Manfre’s first tenure between 2001 and 2004.

R-Section Cop Chase Ends in 3 Arrests and a Crash; Rymfire School Briefly Locked Down

| December 3, 2012

Three men are in police custody this morning, one of them after a lay-over at Florida Hospital Flagler, following a chase through Palm Coast’s R Section that ended with an SUV’s crash in the middle of Royal Palms Parkway.

Flagler Sheriff’s Sgt. Roster, Accused By His Own Men, Is Demoted Over Falsifying Records

| June 18, 2012

An internal affairs investigation of Jamie Roster found he’d falsified time sheets by booking at least $8,406.26 he’d not worked for. The investigation was triggered by complaints from men under his supervision, and reveals strains and morale issues at the sheriff’s office. Roster, demoted to deputy, is appealing.

Maj. David O’Brien Replaces Chief Look as Sheriff Fleming’s 2nd in Command

| February 29, 2012

Flagler County Sheriff Don Fleming appointed Maj. David O’Brien, a 29-year-veteran of the department, his chief deputy, replacing Rick Look, who left the agency he’d served since 2005 late last year.

Chief Rick Look, Ailing, Will Not Return to Sheriff’s Office; Maj. O’Brien Likely Successor

| January 19, 2012

Chief Rick Look joined the Flagler County Sheriff’s Office from FDLE in 2005. His retirement, while not yet official, had been known for some time. He’ll be drawing disability as Maj. David O’Brien, acting chief since last year, takes over.

Miranda Vows: Commissioner Milissa Holland and Undersheriff O’Brien Will Marry April 21

| January 16, 2012

WNZF’s David Ayers exerted the confession about the upcoming wedding from David O’Brien, the undersheriff, who had done his best to keep the news of his wedding to Milissa Holland an open secret.

School Board Votes 4-1 To Allow Tasers Back on Campuses, With Vague Conditions

| October 5, 2011

School Board member Andy Dance wants the superintendent to develop a school-centered policy with the sheriff on using Tasers, but the sheriff’s office is resistant to mixing school policies with its own.


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