Brushy Bill Roberts, supposedly around 1889
Brushy is roughly twenty-nine in this photo. Allegedly, it was taken around 1889 when Brushy claimed to have been riding in the Anti-Horse Thief Association.
Brushy Bill Roberts, supposedly around 1892
This photo of Brushy Bill was supposedly taken around 1892, when he was thirty-two and working for the U. S. Marshal Service.
Possible photo of Brushy Bill Roberts in 1898
This photo, taken in Cuba in 1898, shows five members of the Rough Riders. It has been supposed the man fourth from left bears a resemblance to Brushy Bill, who claimed to have ridden with the Rough Riders. However, as there seems to be no documentation supporting Brushy's claim, it's doubtful he was a Rough Rider, let alone able to stand for a photo with them.