First, before we delve into the brief 13-year existence of the infamous Ashley Gang that terrorized the Treasure Coast and came to an abrupt end in Roseland, let me inform you about the Ashley Gang.
John Ashley, the ringleader of the gang, first murdered a man, attempted to rob a train, robbed several banks, made several jail and prison escapes, and had several shootouts with law enforcement.
Bootleg Moonshine, who became a roadrunner, acted as a modern-day pirate and had a hideout in the Everglades.
He did all this while maintaining close family ties, helping less fortunate people along the way, and managing a love affair with a woman named Laura Updegrove. Newspapers of the day periodically compared John Ashley to Jesse James, the infamous outlaw
of the Wild West.
Yet among the poor people known as Florida Crackers, John Ashley was hailed as somewhat of a folk hero, a type of Robin Hood, sometimes called a Swamp Bandit or the King of the Everglades.
John Ashley was born in 1888 to Joe and Regina Ashley in Fort Myers.
He was one of ten children.
He had five sisters and four brothers, some who would become members of his gang.
John's father and brothers were woodchoppers, hunters, and fishermen, and were crack shots.
In 1911, the family moved to West Palm, chopping wood for the railroad.
John and his brother Bill became trappers and friends with the Seminoles, and their father Joel and the other sons soon started operating a still and bootleg moonshine at
West Palm Beach.
In December 1911, John Ashley and DeSoto Tiger, the son of Seminole Indian chief Tom Tiger, left camp by canoe to take their 84 otter hides to market in Miami. John arrived alone and sold the hides for $1,200.
That was about four to six times the average yearly pay at the time, which was between
$200 and $300 a year.
On December 29, 1911, DeSoto Tiger's body was found by Captain Fowry and his crew while dredging a canal from Lake Okeechobee to the Atlantic Ocean.
Sheriff George Baker dispatched deputies to find John, but he and his brother Bob held the deputies up and disarmed them.
John gave them the following message, quote,
Tell Baker not to send any more chicken-hearted men with rifles or they're apt to get hurt, end quote.
Following the encounter with Sheriff Baker's deputies and the fact that he was a wanted man in 1912, John fled the state and went to New Orleans where he worked on a boat.
Then he went to Seattle, Washington to work in a logging camp.
After all, he had experience chopping wood.
Sometime between 1912 and 1913, the Ashley family moved to Gomez, which was about two miles north of Homestown in Martin County, Florida.
This later became home base for the gang.
John got homesick in 1914, returned to Florida, and surrendered to Sheriff Baker.
He admitted killing DeSoto Tiger, but pleaded self-defense because DeSoto threatened to kill him if John didn't give him some liquor. John figured the Florida Crackers wouldn't convict him for killing an Indian.
On July 3, 1914, John was tried for the murder of DeSoto Tiger, but the trial ended in a mistrial.
Nine jurors voted for acquittal.
Three voted guilty as charged.
The prosecutors then asked for a change of venue to Dade County.
The Ashleys were alarmed at this.
Deputy Bob Baker escorted John uncuffed to the jail.
When Baker went to unlock the door, Ashley bolted over the fence and disappeared into the darkness.
John then hid out in the Everglades with three criminals, Kid Lowe, a bank robber, Clarence Middleton, a dope addict, and Roy Matthews.
In early February 1915, John and his gang tried to rob passengers on a Florida East
Coast railway train south of Stewart, but the attempt was thwarted by a quick-thinking porter who locked the doors between cars after hearing screams from a woman passenger. On February 26, 1915, John, his brother Bob, and Kid Lowe robbed the bank of
Stewart, netting $4,500.
The robbers started firing their guns to show they meant business.
Kid Lowe accidentally or on purpose shot John, shattering his right jaw, which ultimately caused him to lose his right eye.
From that day forward, John and his friends would be known as the Ashley Gang.
Six days later, John's brother Bill called Dr.
Anna Darrow, the doctor of the Everglades or the swamp doctor, to attend to John.
She was blindfolded and then taken 10 miles into the glades to the Ashley Camp to treat
John.
Somehow, Sheriff George Baker learned of the location of the camp and DeSoto Tigers Brothers led the posse to it.
The posse surrounded the camp and John was arrested.
He was taken to the Palm Beach Jail and was treated.
However, he refused to let the doctor remove the bulletin in his head.
The doctor had removed his right eye, which was later replaced with a glass eye, and for a while John wore a patch.
By the end of March, John Ashley was transferred to Dade County Jail in Miami for his second trial.
Before questioning potential jurors, the judge stated that those who were sick, deaf, or had other ailments could be excused.
The judge was surprised to hear of so much sickness.
About 75 potential jurors were excused that day.
On April 6, 1915, the trial was short and John was found guilty of murder.
He was sentenced to be hanged, but his lawyers appealed the sentence.
On June 2, 1915, Bob Ashley traveled to Miami to free his brother from jail.
When Deputy Sheriff Wilbur Hendrickson opened the door of his house after Bob knocked, Bob shot him and took the keys to the jail.
Mrs. Hendrickson attempted to shoot Bob and in his haste to make a run for it, he dropped the keys.
Bob stopped the driver, commandeered his car, but two policemen overtook him.
One Officer Bob Riblett attempted to arrest Bob, but Bob shot him.
Then Bob Riblett shot Bob.
Both Bob Ashley and Officer Bob Riblett died at the hospital that day.
Five months later in November 1915, John Ashley attempted to break out of the Dade County
Jail by digging his way out with an iron spoon.
He dug for five weeks and was two feet away from freedom when his plan was discovered by a jailer.
Despite the failed jailbreak attempt, his attorneys were successful in having his death sentence reduced to 17 and a half years in the Penichet Tree in Rayford, Florida the next year.
John Ashley entered Rayford Prison, southeast of Lake City, on November 23, 1916.
For one and a half years, he behaved as a model prisoner, and because of his good behavior,
John was sent to a road camp on March 31, 1918.
In July 1918, however, John escaped with the assistance of fellow prisoner, a bank robber
Tom Maddox, and fled to his hideout in the Everglades.
He and fellow gang members sold their bootleg Moonshine and operated three stills for the next few years. In 1920, Laura Updegrove decided she didn't want to be married anymore to Buck Tillman to take care of their three kids under age five, so she asked
to join the gang.
Laura even packed a .38 caliber revolver strap to her waist.
She proved to John that she was a good marksman by hitting all the targets he set for her to shoot.
Laura became a lookout for the gang.
She warned fellow gang members when she heard law enforcement getting close to the gang's hideouts.
She cased banks, directed the delivery of liquor, and served as a getaway driver.
Being closely associated with John Ashley named King of the Everglades, she earned the nickname the Queen of the Everglades.
When the Prohibition Amendment went into effect in 1920, brothers Ed and Frank became rum runners by transporting liquor from Bimini in the Bahamas to Jupiter Inlet and Stewart.
Sheriff George Baker died in 1940, and his son Robert succeeded him as sheriff.
During the same year, 1920, John was arrested while delivering moonshine in Wachula about 70 miles southeast of Tampa by Sheriff John Pucher, who was unaware that he had arrested a famed outlaw.
A black man in jail recognized John and revealed his true identity.
John Ashley was returned to Rayford Prison in June 1921.
He was 33 years old at the time.
There he had a dream about his brothers being killed by three rum runners, Alton Davis,
Bo Stokes, and Jim White.
Ed and Frank Ashley continued their bootlicking enterprise despite the close calls they had with the U.S.
Coast Guard.
While both were returning for Bimini one night in early November 1921, they got caught in a sudden gale and disappeared.
Their bodies were never found.
The three rum runners, Alton Davis, Bo Stokes, and Jim White disappeared three months after
Ed and Frank Ashley died.
Despite the loss of brothers Bob, Ed, and Frank, the Ashley gang still continued on with their bootlegging, rum running, and bank robberies through the 1920s even while
John was in prison.
Laura Updegro was said to have carried a lot of influence of the gang's activities.
The gang also stole cars, hijacked boats, robbed stores.
They even intercepted rum runners' boats along the coast of Florida, which amounted to piracy on the high seas.
Eventually, the gang toned down their liquor piracy and concentrated on robbing banks, which is more their specialty line of work.
People along the Treasure Coast lived in constant fear of the gang.
Many people paid protection money to the gang, yet others helped them along the way.
The gang expanded their activities into the central part of Florida.
It has been rumored the gang stayed at the Fellsmere Inn since revolvers and a rifle were found upstairs bedrooms.
According to the locals, the gang was not all bad.
It was some redeeming social value.
It has been said the gang left money under a brick for a poor, ill individual.
They left groceries for a widow, and they decided against robbing a bank when one member of the gang recognized his childhood friend, and they spared the life of a deputy sent to hunt them down when he begged them not to shoot.
In 1923, John's nephew, Hanford Mobley, who had dropped out of school, and Roy Matthews led the gang.
Once again, the gang robbed the bank of Stewart, during which a teenage Mobley was disguised as a woman.
John escaped from the Rayford Prison Road Gang in September and November 1923.
The Ashley Gang robbed a bank in Pompano and carried away $5,000 in cash and $18,000 in securities.
As John left the bank, he also left a bullet with a cashier as a souvenir of a career as a bank robber. Then the gang left town in a stolen taxi, waiving a bottle of whiskey to bystanders along the
street and shouted, We got it all! Furious and frustrated by the gang's increased lawlessness, Palm Beach County Sheriff's deputies spent months searching the Everglades to find the gang's hideout, but to no avail.
On January 10th, 1924, Sheriff Bob Baker of
Palm Beach County acted on a tip, rounding up a posse.
The posse arrived at dawn the next day, open fire, killing John's father, Joe, inside his tent while trying to put his boots on.
John then shot and killed Sheriff Baker's cousin,
Fred Baker.
John fled into the swamps for the other gang members to escape the posse.
Laura Updegrove was seriously wounded by buckshot, and the police held her in custody following the raid.
People were so enraged at the killing of Fred Baker that they burned down the gang's camp, the Ashley home, and the Mobley home that was the home of John's nephew.
Later that same year, John and his nephew, Hanford Mobley, stole a boat, led a pirate-like raid on some run-runners in the Bahamas, and returned to Florida with $8,000 in money and liquor.
In October 1924, John decided that he and his gang would travel north to his sister
Daisy's house in Jacksonville to plot his revenge, rob a bank along the way, and return after the November elections to kill Sheriff Bob Baker.
He decided not to take Laura with him, who was seemingly was spending a lot of time with another gang member, Joe Tracy.
John was a very jealous man.
On November 1st, 1924, Sheriff Baker received a tip revealing that the Ashley gang was on the move and would be traveling up the Dixie Highway to Jacksonville.
Sheriff Baker knew the gang had to travel over the long wooden bridge over the St.
Sebastian River between Roseland and Micco.
Being at the bridge was in St.
Lucie County at the time, and it was out of his jurisdiction.
Sheriff Baker sent a telegram to St.
Lucie County Sheriff Merritt and asked him to intercept the gang on the St.
Sebastian River bridge.
Merritt agreed at once to cooperate, and Baker sent four deputies to assist Merritt and his deputies.
The deputies borrowed a chain from a Sebastian resident, J.T.
Thompson, stretched across the bridge to block traffic.
Being that it was dark, they hung a red lantern in the middle of the chain and waited in the bushes along the side of the road.
The unsuspecting Ashley gang took their time in traveling up the coast.
In fact, they stopped in Fort
Pierce so John could get a haircut and a shave and play some pool afterward.
By the time the gang left town, it was dark.
The St.
Sebastian River bridge lay 28 miles to the north of Fort Pierce.
An hour after the chain had been placed on the bridge, John Ashley's black touring car was seen headed towards the bridge.
When John Ashley and the gang arrived at the bridge, they had no choice but to stop.
Immediately, the deputies came out of the bushes and descended upon the car.
Inside were John Ashley, age 36, his nephew, Hanford Wogley, age 18, Ray Lynn, age unknown, and Clarence Middleton, age 25.
The deputies ordered the gang out of the car.
Each gang member had a rifle and hosted revolver at their sides.
Supposedly, the deputies disarmed and handcuffed the four gang members, but whatever happened, history records that all four were shot and killed that night on the bridge.
John Ashley, Hanford Mogley, and Ray Lynn were buried alongside each other in the Ashley family cemetery in Go Miss.
Their graves now lie inside the Marita Sands Country Club in Martin County.
Clarence Middleton was buried in
Jacksonville. As for DeSoto Tiger's family, once they learned of John Ashley's death, they felt that DeSoto's death had been avenged.
Some of the Ashley and
Mobley children changed their names, and for good reasons.
Laura Upthegrove lived under an assumed name after John was killed.
She eventually opened up a gas station canal point on Lake Okeechobee and lived with the mother in Upthegrove Beach.
She still continued to bootleg liquor, though.
August 6, 1927, Laura Upthegrove became involved in a heated argument with a customer over the sale of moonshine.
She jerked a bottle of Lysol off the shelf, drank it, and died within minutes.
No one was sure whether or not she grabbed the wrong bottle and thought the Lysol was gin, but when she took a swig and swallowed it, her life came to abrupt end that day at age 30.
Years later, it was revealed by a relative that once Laura learned that John Ashley was not was going to leave Florida and not take her with him, she was one of the who told one of the sheriff's deputies that John was on his way up the Florida coast and
Dixie
Highway. The next time you drive north on US Highway 1 in Indian River County, and you have the time, take Indian River Drive just south of Sebastian and travel north along the scenic shore of the Indian River.
When you come to the north end of Indian River Drive at US 1, to the right you will see Moore's Point historical marker.
It only takes a minute to read and realize that on the night of
November 1st, 1924, the most notorious gang of criminals ever to terrorize the
Treasure Coast, the Ashley Gang, was snuffed out of existence forever on a wooden bridge over the St.
Sebastian River just north of Roseland.