The intriguing question is "did the infamous dentist turned gunman, John Henry "Doc" Holliday travel through Pensacola?" According to Victoria Wilcox, the famous sheriff Bat Matterson stated in a 1907 article that Doc was forced to leave his home in Valdosta, Georgia very quickly to escape possible prosecution. Because of this, his family decided it was best for him to head for Texas. Researchers have investigated the "why's" and "what for's" of his departure, but if he did run then what direction did he take? According to Wilcox, the quickest route would be to cross over the nearby state line into Florida and hop a train for Pensacola, the next major shipping port to the west. Ms. Wilcox offers a believable theory based on some old letters found in a trunk by a junk dealer in Waycross, GA. He had purchased the trunk, which had belonged to an elderly person who had passed away. Inside were some old letters postmarked "Pensacola, FL." What caught his eye was that the signature was from a "John Henry Holliday." Ms. Wilcox stated that the junk dealer had "never heard of Doc being in Pensacola or any other Florida town, so he threw away the photos and the letters and sold the trunk to a customer who liked antique boxes.
What the junk dealer didn’t know was that Holliday’s cousin, Clyde McKey, had family living in Waycross, and the box and the photos and the letters had likely once to her daughter. They were probably sent by John Henry Holliday as he stopped over in Pensacola on his way West." Another local story reported by the website "Pensacola Then and Now" is that "Doc Holliday arrived in Floridatown in 1873 when he was dropped off by the Pensacola-Georgia Railroad. The railroad porter told him he would have to take a ferry across Escambia River to get to his destination in Pensacola. This circuitous route was because from July to November the trains were not allowed to make entry into downtown Pensacola. This was because of their fear of the dreaded Yellow Fever epidemics that plagued the area. In addition, all ships were quarantined for one month at the Navy Yard. The porter told him that a ferry ride was the only way to get into Pensacola and it cost two bits (.25). Holliday told the porter that Floridatown "looks like paradise, like heaven almost."
When Doc finally made his way into Pensacola, he took lodging at the Tivoli High House. This was a two story inn near Seville Square and was Pensacola's first dance hall (built in 1805). While there, he ventured over to South Palafox Street into the Grand Prize, which was a saloon on the waterfront. It was full of sailors doing what many did in those days! They drank, gambled and looked for the nearest "sporting woman," "soiled dove," or "fallen angel" as they were called at the time. While playing poker, Doc noticed that a nearby sailor had a streetwalker on his lap. He noticed the young girl was VERY young. After watching her disturbed expressions, Doc pulled his pistol on the drunk sailor, telling him this was by no means proper. He then realized he was the only gentleman in the saloon full of ruffians. He was jumped from behind and punched and kicked. Hearing the fight, the owner of the saloon came in and broke it up. He told Doc to leave because he was not going to have anyone come in and ruin his business for his patrons. If he didn't leave he was going to call the authorities.
Upon leaving, he was given his pistol back by order of the owner and he walked back to the Tivoli High House. When his ship, the "Golden Dream," docked at the Commendencia Street Wharf, he boarded and set sail for Galveston, Texas never to return." Interesting story, but we'll probably never know the truth of the tale!
John Henry "Doc" Holliday
Old Floridatown Andrew Jackson Hotel 1909
Wyatt Earp, long time friend
of Doc Holliday (1848-1929)
Doc Holliday in the famous 1881 Shootout at the OK Corral