L-R: Billy Bowlegs III, Wilson Hoquid, Tommy Doctor.

The date of the picture is unknown. I could not find any info for Wilson Hoquid or Tommy Doctor.

I did find some information on Billy Bowlegs III. He was a Seminole Elder and Historian. Father was Black and Mother Seminole. The picture appears to be from around 1895 to 1900. The shotgun seems to be (to my untrained eyes) a Winchester Model 1893.
Wilson Hoquid has what appears to be a Smith & Wesson Model 1 on his waist and maybe a Sharps Rifle? A hint would be the cartridge belt he is wearing. Tommy Doctor also has a shotgun, but I can’t see enough to try to figure what is it.

It is unfortunate that the only association that people make with Florida and Cowboys has the word cocaine inserted in the middle. There were cowboys in Florida long before they were the stuff of Western legends and they are still taking care of the hoofers in the 21st Century. The use of whips to haul cattle gave them the moniker of “crackers,” today used in a derogatory manner.

As for the Seminoles? Well, you cannot but like a tribe who took all comers, lived in the damned swamp dressed like that and told the all-powerful NCAA to go pound sand and to leave the  Florida State mascot alone as they were damned proud of it.