By Mike Simmons
Here is an interesting photo of the Pensacola Police Force, posing on the front steps of Pensacola City Hall, which is now the Pensacola Museum of History.
Note the new “8-point” police hats that the officers are wearing. The eight points around the top of the hat are symbolic of the eight original members of the first Watch, in Dutch colonial New Amsterdam. Also notice the double row of buttons and the PPD badge on the new, modern uniform coats. Each officer is wearing a tie, which was a requirement. The plain-clothes officers were not called detectives or investigators, but “Special Officers.”
This photo lists the names of the officers. Notably are:
Chip Shackleford (later Sgt.), who died in the line of duty on February 27, 1933

The Chestnut brothers – Occie and William, cousins of Retired Captain Steve Davis.


Millard Kelson, uncle of Retired Supervisor Dixie Kelson Chancellor. He later was elected as County Constable.


Riley Simmons, uncle of retired Sgt. Mike Simmons. He later became Assistant Chief and killed the suspect who killed Officer Hatcher in 1939. After retiring from PPD, he became a deputy with Escambia County Sheriff’s Office and died in the line of duty.

Chief E.E. Harper, who later became police commissioner and whose son, Raymond Harper, was a long-time PPD captain.


Assistant Chief Willie O’Connell, who later became chief and served in that position 20 years, longer than any other chief.

A historical photo for sure…

EE Harper was my Granny’s brother. I got my middle name from Raymond. My dad was on the force, Harvey Jackson. Enjoy you history of the police department. Ray Jackson
Thanks, Ray. When my father, Jim Simmons, was on the force, I spent time hanging out at the station. I knew Harvey and Raymond. Both were good men.
Great photos, Mike! How did your uncle die? Man, sorry to hear this! Appreciate all of your work, brother!
Chris, after Riley’s retirement from PPD, he sat around the house for a couple of years. Bored, he decided to go work for the Escambia County Sheriff’s Office. His brother-in-law was Sheriff R.L. Kendrick, the current sheriff. One day, while Riley was riding with the sheriff on patrol, he suffered a major heart attack. Sheriff Kendrick rushed him to the hospital, but he died shortly thereafter. I didn’t know we were related until a few years ago. Thanks for asking.
He gave his ALL. So appreciate your work!
Love the photos
Thanks, Jim!