Defiant to the end

Laura Upthegrove and John Ashley
After two failed marriages and four children, Laura Upthegrove decided to join John Ashley’s notorious gang on the east coast of Florida. STEVEN CARR ELLIOTT MUSEUM

Bootleg booze and blazing bullets pockmarked the short and tragic life of Laura Upthegrove, girlfriend of notorious gangster John Ashley


Anyone familiar with Treasure Coast history certainly knows the story of the notorious Ashley Gang. It was a group of despicable outlaws — murderers, rum-runners and bandits — during the 1910s-20s led by John Ashley, whose parents lived in Fruita, near Gomez and Hobe Sound, in what is now southern Martin County. John’s girlfriend and gun moll, Laura Beatrice Upthegrove, perhaps not as well-known, was nevertheless an important member of the gang.

Ashley was prisoner No. 12501 at Raiford State Penitentiary
Ashley was prisoner No. 12501 at Raiford State Penitentiary. LUCKHARDT COLLECTION

Her life was mostly one of unhappiness and tragedy. Afraid of no one, she had the grit, determination and spunk of a frontier woman, probably better suited for a life in the Wild West of the 19th century.

Laura was born on Oct. 5, 1896, in Reddick, near Ocala, the first of nine children of John William Upthegrove and wife, Emma Rebecca Kittler. Her ancestors moved to Florida in the mid-1800s when William Hendry Upthegrove of Pennsylvania came to the Gainesville area. A few years after Laura’s birth, the family was living in Island Grove in Alachua County, where John was a farmer.

When Laura was just 14, she married Calvin Carlton Perry, a man 12 years older who was a driver for Standard Oil Co. and a fisherman in Fort Myers. A year later, she gave birth to a son, Wilson Conrad, followed by a daughter, Vera Elsa, in 1915; two children and she wasn’t even 19 years old.

The couple divorced in 1916 and Laura married Earnest Adair “Buck” Tillman, a marine engineer. In July 1917, a son, Clarence, was born to the Tillmans, followed by a second son, Sidney, in February 1919. By this time, Laura’s family had moved to Long Beach on the eastern shore of Lake Okeechobee, which eventually was named Upthegrove Beach, just north of Port Mayaca. Laura, Earnest and the children, all under the age of 5, lived next door to the Upthegrove family.

Jimmie D. Rebecca Padgett's death certificate
Laura’s daughter, Jimmie D. Rebecca Padgett, died after swallowing an open safety pin and was buried in West Palm Beach. LUCKHARDT COLLECTION

It was evident by early 1920 that rebellious and carefree Laura was not content to be married with children. Suddenly one day she announced she was leaving, with plans to join the notorious Ashley Gang on the east coast of Florida. Finding Ashley was fairly easy for Laura, who would meet up with him at a mangrove region called Peck’s Lake near Manatee Bay in Salerno, although other accounts indicate the two may have already known each other.

To join the gang, Ashley wanted to know if Laura could handle a gun. She obligingly demonstrated, shooting off rounds with a .38 revolver, hitting every target. It was decided that she would scout banks and other establishments for potential robberies and she often drove the getaway car. Laura proved to be brilliant in planning the gang’s activities in executing bank robberies, hijacking illegal liquor and figuring how gang members could escape when jailed. She wore a .38 on her right hip and was ready to use it.

The gang was extensively involved in rum-running activities including hijackings, and Laura played a vital role in those operations.


Laura Upthegrove
After Laura joined the gang, she would scout banks looking for potential robbery sites and often drove the getaway car. STEVEN CARR/ELLIOTT MUSEUM

Although never considered a real beauty, Laura was attractive in some ways, taller than most women, with piercing black eyes, dark hair and tanned skin. She and Ashley were soon lovers and devoted to each other, but Laura’s innocent flirtations with other men made him insanely jealous.

In April 1922, Laura cased the Bank of Stuart, which had been robbed seven years earlier by Ashley, his brother, Bob, and a young man called Kid Lowe. Eventually, Ashley was caught, tried, sentenced to 17½ years and sent to Raiford State Penitentiary. In June 1918, he escaped, but was recaptured in June 1921 and returned to Raiford. However, Ashley was still able to provide instructions for holding up the Stuart bank a second time.


In spite of being a member of the Ashley Gang, it appears Laura was not completely faithful to Ashley and the gang. She began seeing Hugh Bub Padgett, a strikingly handsome fellow, after Ashley returned to prison. Laura knew Padgett because his brother, Noah, was married to her sister, Lola.

In early November 1921, while still involved with the gang, Laura became pregnant. During the later months of her pregnancy, she stayed at her mother’s Canal Point home and on July 31, 1922, gave birth to a daughter, Jimmie D. Rebecca Padgett.

Laura never married Padgett, although he was named the father on the baby’s birth certificate. Tragically, nine months later while living in West Palm Beach, the child swallowed an open safety pin. The pin lacerated her stomach and the child went into shock and died. She was buried at Woodlawn Cemetery. It is unknown if Padgett was ever notified of his daughter’s death.


John Ashley
Ashley was the leader of a gang that pulled off a number of bank robberies in Martin County in the early 1920s.

Meanwhile, Ashley, who had been a model prisoner at Raiford, was assigned to a road gang. On Sept, 27, 1923, he escaped for a second time by bribing a guard and headed straight for the Everglades. Two other gang members, Ray Lynn and John Clarence Middleton, also escaped from a prison in Marianna and later met up with Ashley. Once again, he was back in control of the gang and Laura was back with her lover.

The hijacking of other smugglers’ liquor and stealing cars increased up and down the east coast during the rest of 1923. Whenever it was necessary, the gang slipped back into the swamps, mangroves and underbrush of the Everglades for protection.

At 6 a.m. on Jan. 9, 1924, Sheriff Bob Baker led a raid at one of the gang’s liquor stills 1½ miles from the Ashley home in Fruita. Baker and a 50-man posse came in with guns blazing. The major gun battle resulted in the death of Deputy Sheriff Fred Baker, a cousin of the sheriff, and Joe Ashley, the patriarch of the family. Laura was shot in the hip and her loud screaming distracted the deputies, allowing Ashley to escape. Other family members, including his sisters and his mother, were hauled off to jail while their homes were set on fire by outraged citizens. The sisters and mother were later released.

After treatment for her injury, Laura was arrested in connection with the death of Fred Baker and remained in the Palm Beach County jail. Bail was finally set at $5,000, but was later reduced to $2,500 and she bailed out.

After a few months of hiding in the Everglades, Ashley and Laura met up again. Over time, the gang set its sights on rival illegal liquor operations out of the Bimini Islands in the Bahamas. In mid-1924, the gang attacked the harbor at West End, Grand Bahama Island, stole cash and destroyed storage buildings and docks. Ashley was now an American privateer damaging the property of a British crown colony.

The gang struck again on Sept. 12, 1924, at Pompano Bank. Its heist amounted to $4,000 in cash and $5,000 in bonds. A couple of days later, gang members successfully stole five city-owned automobiles housed near the West Palm Beach police headquarters.

Meanwhile, Laura had to appear in court on the murder charge from the raid on the Ashley camp. She asked for a court-appointed attorney and Sidney J. Catts Jr. was named. Her trial was set for Oct. 6, but the state attorney requested a delay until February.

Then on Nov. 1, sheriff’s deputies and chiefs of police captured four gang members, including Ashley, as they drove north at night along A1A. They were stopped at the Sebastian Bridge by the seven lawmen sent by Sheriff Baker. Laura was not in the car; the plan may have been for her to join them once they were in Jacksonville.

The officers were not taking any chances after stopping them, feeling “it was them or us.” When one of the handcuffed outlaws reached for his hat, the lawmen fired their rifles repeatedly, killing them.

Ashley, Lynn and Mobley were buried in the Little Ashley Cemetery
Ashley, Lynn and Mobley were buried in the Little Ashley Cemetery, where the Ashley family home once stood, now part of Mariner Sands.


Hanford Mobley, left, and George F. Mario
Hanford Mobley, left, and George F. Mario, brother-in-law of John Ashley, were members of the Ashley Gang. Mobley was killed, along with Ashley, Ray Linn and Clarence Middleton, during a sheriff’s ambush on a bridge over the St. Sebastian River near Roseland. SANDRA MARIO PROVENCE COLLECTION

A great deal of speculation has surrounded the circumstances of how Baker learned that the Ashley Gang was headed for Jacksonville. It has been noted by many sources that an informant spilled the gang’s plans that day. Some even say it might have been Laura. It wasn’t until 1976 when one of the key officers present at the killing, Stuart Police Chief Oren B. Padgett, wrote his recollections of that day, 52 years earlier.

Chief Padgett:
I was walking down the sideway about mid-morning this Saturday. It was a beautiful morning; the sun was shining and it was warm; the birds were singing and everything was just beautiful. I walked by a grocery store where George F. Mario [brother-in-law of John Ashley] had just walked out and was putting some supplies in his car. I stopped and spoke to George and we started talking and passing the time of day. I asked him if he had anything new at all, he looked all around and saw that there was nobody nearby to hear what he said. He said, “Yes, they are leaving tonight and they are going to California. They are going as far as Jacksonville tonight and will lay up there tomorrow at John Ashley’s sister, Daisy’s, house and they will continue traveling at night until they get to California. They will be traveling in this automobile that I am putting these supplies in. They’re going to leave later today and there will be four of them.”

Continuing, Padgett wrote:

I thought the situation over very carefully, pondered it in my mind a little bit, went on down to my office, sat around and talked a while to some of the boys. Then I went out and rode around a little, trying to figure out just what to do, if anything. I decided to call Sheriff Bob Baker of Palm Beach County, of which Stuart was a part of that time. For fear that somebody might overhear me talking on the telephone in my office, I went to my home and called Bob Baker on my private telephone. And in talking to him, I did not want to give the name of my informer — I did not want to tell him of the information and how I got it. One of his first reactions was, “Padgett, you better watch this kind of information — if they can get you out of town this afternoon, they’ll rob that bank again.” It was then that I assured him that my information was correct.

Chief Padgett had known Mario for years and trusted him. Did surviving Ashley family members learn that he was the informant? Mario was with the last remaining Ashley brother, Bill, on Dec. 2, 1932, in a small rowboat on the South Fork of the St. Lucie River when the boat overturned. Bill Ashley survived while Mario drowned. The death was ruled accidental.

Laura Upthegrove
Since she was a known bootlegger and gambler, Laura was not welcomed in some communities and spent her life after Ashley’s death moving from one town to another. STEVEN CARR/ELLIOTT MUSEUM


Laura Upthegrove and John Ashley
Laura and Ashley reportedly began their life of crime after meeting in the mangrove region called Peck’s Lake near Manatee Bay in Salerno. NOTORIOUS ASHLEY GANG

With the death of Ashley, the courts dismissed the murder charges against Laura. State Attorney George W. Coleman based his motion on the grounds that Laura was just an accessory.

Laura was totally distraught, discontented and restless without Ashley. The remaining members of the Ashley family treated her as an outcast.

Since she had attained notoriety, especially as a known bootlegger and gambler, she was not welcomed in some communities. She moved to Okeechobee but was arrested several times for public drunkenness and eventually was asked to leave.

Having a man in her life was still essential to Laura. She met Leon E. Lawrence, who immigrated to the United States in 1923. The couple married on Feb. 11, 1926, in Martin County. But the marriage did not last and in early 1927 the couple divorced in Palm Beach County.

Restless, Laura wandered to different locations, being arrested several times for displaying a gun or causing a reckless commotion. She was sentenced to 30 days in Jacksonville for drunkenness in March 1927. While there, she sparked the Pea Farm Cabbage Riot only five days after arriving. She and four other female prisoners demanded that candy be served rather than cabbage on the daily menu. Ultimately, the situation ended when the women were tear-gassed and gave up; Laura was then put in solitary confinement. Upon being released, she returned to work at the gas station at Canal Point owned by her mother.

marriage certificate
Laura married her fourth husband, 34-year-old bachelor Charles Milton Swindal, on Aug. 11, 1927, in Highlands County, five days before she died. LUCKHARDT COLLECTION


Possibly on a whim, Laura married a 34-year-old bachelor, Charles Milton Swindal, on Aug. 11, 1927, in Highlands County.

Laura Upthegrove Perry Tillman Lawrence Swindal's death certificate
Laura Upthegrove Perry Tillman Lawrence Swindal was buried in an unmarked grave in West Palm Beach, after committing suicide. LUCKHARDT COLLECTION

Five days later, Laura was at the Upthegrove gas station. She had sold a bottle of illegal whiskey that afternoon to a customer and he had returned to complain about the liquor’s quality, demanding a refund. E.P. Padgett was visiting the area and riding with Palm Beach County Deputy Sheriff Archibald Brownlee when the two stopped at the gas station to see Laura. When they did, they witnessed her chasing the man out of the store and waving a gun as he quickly drove away.

Laura’s rage continued as she went back into the station where her mother took the gun away from her. Still fuming, she reached for a bottle of disinfectant, swallowed its contents and almost immediately collapsed. Padgett grabbed Laura and attempted to move the seemingly lifeless body to a bed while shouting for someone to get a doctor. Her mother said it was best to let her go. No doctor was needed. Within minutes she was dead. Many thought of it as Laura’s last defiant act in a lifetime of defiance toward the world.

Laura Upthegrove Perry Tillman Lawrence Swindal was buried in an unmarked grave in Woodlawn Cemetery, West Palm Beach. Her mother was the administrator of Laura’s estate, which included several pieces of property and a house in Okeechobee, a house in West Palm Beach and real estate in Hollywood. Laura’s younger brother, Dewitt Upthegrove, handled the estate.

There was speculation at one time that Laura may have buried some of the loot that the Ashley Gang had accumulated at the Canal Point gas station, but nothing was ever found. It had been estimated by authorities that as much as a million dollars may have been stolen or otherwise accrued from illegal activities by the gang through the years, some of it being spent or even given to the needy. Since Laura had several pieces of property at the time of her death, speculation is that they might have been acquired with the cash seized by the gang.

Newspapers of the day called Laura “Queen of the Everglades,” a no-nonsense woman who was as capable as any man of living in the wild glades and hammocks.

See the original article in the print publication

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