The Overstreet family was destined to grow and become known as “The Overstreet Gang” for their grit and tenacity, a necessary quality for survival in this time period, especially for the family businesses: cattle and moonshine.
The first Overstreet arrived in the area from Georgia in the 1850s, William Rabon Overstreet, settling in the Fort Dade area. He established a larger homestead in Dade City. William Rabon Overstreet and his brother Silas, a doctor, both fought in the Third Seminole War. (Two of their sisters were killed in a Seminole raid at their home in Madison, Georgia). William Rabon joined the Confederate Army, was injured and discharged in 1862, recovered then re-enlisted. Unfortunately, he was captured at Gettysburg in 1863, then died of malnourishment and anemia shortly after at Ft. Delaware. William left behind a wife and three young sons whose descendants would become known as “The Overstreet Gang.” The family earned this title for their grit, tenacity and their close knit structure in protecting one another in the family businesses: cattle and moonshine. Toughness was a necessity for survival in this time period and the family was able to hold their own with Brooksville’s Lykes Brothers, a major cattle family.
William’s son James Lucious, married three times and had a total of seven children. One of those children was Lawrence Preston (born 1892). Preston along with his brother Taft and Walter Overstreet confronted Charlie Lykes after the Lykes had added 50 of Preston’s cows to his herd while driving their cattle “through the woods on their way to Kissimmee,” according to Overstreet descendant Susan McMillan Shelton. This was a common practice for the Lykes family. Florida was open range for cattle and on their cattle drives, the Lykes would pick up any cattle they encountered on their way to their destination. If you weren’t tough, then your cattle would end up in the Lykes’ herd without any compensation.
However, the Overstreets were tough and they had a reputation for being so. After Preston and his kin confronted Charlie Lykes, demanding “50 new cows by Saturday,” Charlie showed up on Saturday morning at Preston’s homestead with 55 new cattle. Shelton describes the jovial scene of the cattle branding, “Several people from town came to help in the branding and partying. One of them was Robert Sumner. Preston’s wife, Lizzie, made a big supper for all. Later they all spent the night under the trees. The next morning they all returned home.”
The Overstreets took advantage of Prohibition setting up moonshine stills hidden deep in the Withlacoochee swamp lands. From the youngest to the oldest Overstreet (“Grandpa Luce” ie. James Lucious) and everyone in between played a role in the moonshine operation. The young children would act as lookouts and the older boys were decoys who would run off into the woods with the law in pursuit, so the Overstreet men were not captured. The fathers were the providers and protectors and all would be lost without them.
The family of Preston Overstreet experienced this after he was killed by Sheriff Ike Hudson’s Deputy C.C. Walker at one of his stills on the morning of Feb. 25, 1925. Three years earlier, Preston and his brother Paul had been acquitted/found not guilty in a high profile murder of two law enforcement officers: J. V. Walters and Pasco County Deputy A. P. Crenshaw. Walters and Crenshaw had been investigating a possible store arson for insurance money and went out to a ranch along the Withlacoochee to find merchandise that may have been taken out of the store prior to the arson. The two men were attacked and killed near the U-Cross Ranch at close range when heading back to Dade City. Shotguns were used in the crime. Paul Overstreet resided at the U-Cross Ranch and “an automatic shot gun found at the home of Preston and a pistol found at the same place were placed in evidence,” reports the Dade City Banner. It was Paul, Preston and several others driving back to U-Cross Ranch that discovered the bodies and then called authorities from the home of Luce Overstreet. The Dec. 22, 1922 issue of the Dade City Banner contains a lengthy description of the entire trial in which over 30 witnesses were called.
Between the animosity felt for being declared not guilty in the murder of the lawmen and Preston’s refusal to pay “insurance money” to Deputy Walker and Sheriff Hudson (to protect his stills), tensions grew between the parties.
Shelton described the setup which ended in the deaths of Preston Overstreet and Neal Wilson. Preston had heard “the law was not to be anywhere on this side of the county looking for stills,” so he headed out to his stills on the morning of Feb. 24, 1925 with Neal Wilson.
Shelton writes, “The night before, Deputy Walker, a boy who was a Hancock, and Ike Hudson’s son, and four federal agents from Tampa had staked out Preston’s stills. The morning of the 24th, the agents had gone back to Tampa for a case there. Deputy Walker, the Hancock boy, and Ike Hudson’s son waited in the woods. Having no breakfast, Walker sent Ike Hudson to town in their car to get some food.
“Soon after he left, Preston Overstreet and Neal Wilson got to the still. Walker and Hancock were hiding in the palmettos. Preston had laid his gun down. Both he and Wilson had their backs towards Walker. Walker stood up and said, “You are under arrest.” Before they could turn around, both Preston and Neal were shot in the back. Neal Wilson fell dead. Preston was gravely wounded. They were laid on a tarp. Walker and Hancock sat down and ate the lunch that Lizzie had fixed for them while they waited to see if anyone else would show up at the still.”
The account delivered by Susan McMillan Shelton, is based on accounts from “people who were there, the Overstreet family, and the people of River Road Dade City.” In her account, Shelton states that after delivering the bodies to the courthouse, Deputy Walker summoned the son of Deputy A. P. Crenshaw to come see the body of the man who killed his father.
The Feb. 27, 1925 issue of the Dade City Banner reported on the deaths of Preston Overstreet and Neal Wilson. In contrast to the extremely detailed investigation conducted during the trial of Preston and Paul Overstreet in the deaths of the J. V. Walters and Pasco County Deputy Crenshaw, the Dade City Banner reports that the investigation in the deaths of Preston Overstreet and Neal Wilson consisted of merely an “inquest” by Justice of the Peace R.T. McFall and a “verdict was brought in exonerating the officers of all blame.” The article concludes that Justice of the Peace R.T. McFall “empaneled a jury and held an inquest. The verdict of the jury was that Preston Overstreet and Neal Wilson came to their death at the hands of C. C. Walker, deputy sheriff, in self defense while in performance of his duty.”
The article provides the following account, “According to the evidence brought out at the inquest the deputy sheriff and a party of Federal prohibition officers from Tampa located three stills in the woods and decided to wait for the operators to return. After waiting all night without success, the Federal officers were obliged to leave and return to Tampa, as they were witnesses in a case in Federal Court there….
“Shortly after Hudson had left, a car was heard coming and as it approached Walker told his companion to ‘get set.’ In moving into a position where he could rise quickly, Hancock’s gun — a double barreled shot gun — was accidentally discharged. The car containing Preston Overstreet and Neal Wilson, which had approached quite close to where the officers were lying in a clump of palmettos, stopped at the sound of the shot and the two men got out, with their guns in their hands, and Overstreet, who was armed with an automatic shot gun was heard to say “——— ——– We’ll kill ‘em, G——-d, D——–n ‘em.” As the two men came closer the officer saw that Wilson was armed with a 30-30 high power rifle. Both men also carried pistols.
“When Overstreet and Wilson were in about 30 yards of the officers Walker rose up and said, “Gentlemen drop your guns, you are under arrest,” meanwhile holding his gun, an automatic shotgun in his arm. Before he had finished speaking, Wilson had fired, the bullet passing so close to Walker that he said he ‘could smell it.’ Overstreet meanwhile was making preparations to fire and Walker immediately shot him and then at Wilson, emptying his gun before he stopped. Both Overstreet and Wilson fell dead without firing a second time.”
According to relative Steve Overstreet, the law put a large price on the head of Preston’s oldest son and he was forced to hide for several years in the swamps to avoid being killed. Preston’s wife could not defend the cattle by herself with her young children and they were quickly taken by other cattle herds. The family Preston Overstreet left behind had to rely on family members to survive and often his wife and eldest daughter went hungry according to Shelton.
This story is an example of the harsh life that existed in the area less than a hundred years ago. A man is killed, his oldest son has to go into hiding, and quickly the vultures came in and took everything from his family and widow.