JACKSONVILLE, Fla. — In the Brentwood area on Sunday night, a man found himself in legal trouble after exchanging gunfire with undercover officers from the Jacksonville Sheriff’s Office. This marks the third such officer-involved shooting in Jacksonville in 2026.

The Sheriff’s Office reported that task force members were investigating a drug-related complaint on 22nd Street near Main Street North. Officers were conducting surveillance from an unmarked vehicle at the time of the incident.

Authorities say the confrontation began shortly after 7 p.m. when 35-year-old Samuel Cook approached the officers’ vehicle from behind and aimed a gun at them. While it remains uncertain if Cook realized they were law enforcement officers, they were dressed in police uniforms and tactical gear, as noted in the arrest documents.

The officers responded by discharging their weapons and then chased Cook on foot. According to police, Cook fled for approximately two blocks, returning fire as he ran, before taking cover behind parked vehicles. He sustained multiple gunshot wounds during the exchange but eventually surrendered. Cook was transported to a hospital with injuries that were not life-threatening. The Jacksonville Sheriff’s Office confirmed that the officers involved were unharmed.

Cook is now charged with aggravated assault and attempted murder of a law enforcement officer.

Sheriff T.K. Waters addressed the shooting during a news briefing.

“Don’t pull guns on the police, you won’t get shot. If you pull a gun, you don’t have to shoot it first. If you pull a gun when the police comes up, you’re going to get shot.” Sheriff Waters said.

Waters emphasized the danger officers face in these situations.

“These guys are pulling out guns, firearms. It’s a dangerous world. We’re not playing games here. This is not tiddlywinks. This is real life.”

First Coast News crime and safety analyst Mark Baughman, who has extensive experience working in the Brentwood area, says undercover operations like this can be especially dangerous.

“The police officers that work that area definitely have to be on their toes, for lack of a better term, and they also have to be vigilant and make sure that they’re doing what they should do to answer calls,” Baughman said. “I mean, they try to find ways to fit in, blend in better. They try to find ways to do surveillance a little easier and there’s technology out there that’s being expanded, you know, with drone use and all types of things.”

Baughman says these operations are necessary to address ongoing criminal activity and long-standing challenges facing Brentwood.

“It’s been blighted with drugs for a long time. There’s been a lot of other activity, contraband sold up there other than drugs. A high prostitution area in some areas. So all that collectively sometimes draws that criminal element in a very close, condensed area,” Baughman said.

First Coast News asked the Jacksonville Sheriff’s Office if it is considering adjusting operational tactics for undercover or covert officers. 

“The specifics related to last night’s officer-involved shooting will be reviewed by multiple agencies – over the course of the coming months,” the agency responded. “Whether or not recommendations on future processes may be affected would come, if deemed appropriate, following the criminal and administrative reviews by the agency.”