A St. Augustine veteran with more than 323,000 YouTube subscribers is demanding $200,000 from the city of Flagler Beach following a March arrest outside the Funky Pelican restaurant, according to a report.
Describing himself a free speech activist, Jeff Gray, 55, has drawn online renown for filming himself standing outside businesses, city halls and other public areas holding a sign that reads “God Bless Homeless Vets.”
Some of his videos show him carrying a firearm, while others include 911 calls from irritated residents or business owners requesting that officers move him along. Typically, they speak with Gray briefly and allow him to carry on.
But Gray’s one-man demonstrations have also resulted in multiple arrests and written citations in several states.

The Flagler Beach encounter fell into the latter category. Gray, who had a gun in his pocket at the time, was standing on a public sidewalk in front of the restaurant, holding his sign and occasionally telling passersby, “God Bless the homeless vets.”
A staffer called police, claiming Gray was harassing patrons and asking that he be relocated.
Bodycam footage shows a pair of officers engaging Gray, with one telling him to move.
“We can trespass people,” the officer says.

Gray responds that he has the right to stand on a public street and repeatedly refuses to move.
“If you’re a dumb dumb you can think that, dumb dumb,” he tells the officer.
After a final refusal, Gray is handcuffed and taken into custody.
The charges were soon dropped, and the officer involved received a three-day suspension for violating city arrest procedures.
Gray’s attorney, Eric Friday, sent a pre-suit notice to Flagler Beach on Nov. 5, demanding a $200,000 settlement, removal of Gray’s DNA from police databases and anexpungement of the arrest, Flagler Live reported.

The notice alleges civil rights violations and firearms preemption law breaches, noting that state law bars local governments from enforcing stricter gun regulations than the state.
Friday also cited potential additional damages from the delayed return of Gray’s firearm and possible city liability for failing to properly train officers.
Flagler Beach Commissioner Scott Spradley said the $200,000 claim matches the statutory maximum, while Commissioner Eric Cooley praised Gray’s activism but suggested that he was more interested in remuneration than reform.
Police Chief Matt Doughney issued a public apology in August, and the city has implemented policy changes to prevent similar incidents.
“My motivations for doing this type of activism are to teach the general public that we have rights, how to stand up for their rights, and how to teach law enforcement officers top respect our rights,” Gray states on his YouTube channel.
