DEADLY CONSEQUENCES

A 10-Day Digital series from Oct. 23 to Nov. 1, 2024, the 100th anniversary of the end of the Ashley Gang

Part 6 of 10

THE LOVE INTEREST

Laura Upthegrove
ELLIOTT MUSEUM

Laura Upthegrove was John Ashley’s partner in crime and romance

BY GREGORY ENNS

Besides Hanford Mobley, Clarence Middleton and Roy Matthews, another person worked behind the scenes to execute the Bank of Stuart robbery, casing the bank in the weeks before with how-to instructions relayed by John Ashley from prison. Her name: Laura Upthegrove, John’s lover.

Laura likely met John in 1920 during the three years he was on the lam. John had made his first prison escape from the state convict camp at Milligan on July 10, 1918, with Tom Maddox of Madison County and was recaptured in June 1921.

Laura Upthegrove with her first husband, Carlton Collier.
Laura Upthegrove with her first husband, Carlton Collier. SANDRA MARIO PROVENCE ARCHIVE
Laura Upthegrove with her first child, Wilson.
Laura Upthegrove with her first child, Wilson. SANDRA MARIO PROVENCE ARCHIVE

THRILL-SEEKER

The late historian Alice B. Luckhardt, who devoted years of research to the life of Laura, wrote in an article appearing in Indian River Magazine that Upthegrove gave up a life of marriage and motherhood for the thrill of being with John and joining the Ashley Gang.

According to Luckhardt’s account:

The restless Laura was a 23-year-old mother of four children and on a second marriage when in early 1920 she left her husband, Earnest “Buck” Tillman, for a life of adventure with John Ashley.

Laura was born Oct. 5, 1896, and grew up near Ocala, the oldest of nine children. At 14, she married 26-year-old Calvin Collier in 1911 in Lee County. They had two children, a son, Wilson, born in 1912, and a daughter, Vera, born in 1915.

Laura divorced Collier in 1916 to marry Tillman. They had two more children, a son, Clarence, in 1917, and another son, Sidney, born in 1919. Laura’s daughter from Collier remained with her while her son remained with Collier. During this period, the Tillmans had moved to the eastern shore of Lake Okeechobee just north of Port Mayaca, where Laura’s parents had already been living. The place is now known as Upthegrove Beach.

Laura Upthegrove and John Ashley in their last years together. Laura’s uniform and John’s military cap may have been part of a disguise.
Laura Upthegrove with possibly Lake Okeechobee behind her. SANDRA MARIO PROVENCE

MEETING JOHN

But Laura wanted more than a life of marriage and motherhood and her parents living next door. Rebellion stirred in her soul. Reading and hearing about the adventures of John Ashley, she left her husband and children in early 1920 in search of the notorious criminal.

“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,” Luckhardt wrote.

Before agreeing to allow her to join him, John demanded to know whether Laura could handle a gun. “She obligingly demonstrated skill in using a .38 revolver, shooting off rounds that hit every target,’’ said Luckhardt. “Laura would thereafter be an important part of the gang.”

During this period much of the gang’s activity focused on rum-running and hijacking other competing bootleggers. Laura also served as a lookout for the gang and soon became John’s romantic partner.

Luckhardt wrote:

Although never considered a real beauty, Laura was attractive in some ways, taller than most women, piercing black eyes, dark hair and tanned skin. She and John were soon lovers and devoted to each other, but Laura's innocent flirtations with other men made John insanely jealous. However, 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 by local authorities. She wore a .38 on the right hip and was ready to use it.

But their romance was forcibly broken off when John was captured in June 1921. He escaped again the following November 1921 but he was soon recaptured.

ANOTHER MAN

Laura Upthegrove with possibly Lake Okeechobee behind her.
Laura Upthegrove and John Ashley in their last years together. Laura’s uniform and John’s military cap may have been part of a disguise. SANDRA MARIO PROVENCE

While John was in prison, Laura took up with Hugh Padgett, a handsome, red-haired World War I veteran who worked on a dredge digging the St. Lucie Canal. They had met through Laura’s sister, Lola, who married Hugh’s brother, Noah.

Laura was lonely and always desired male attention and companionship. Hugh proved to be just the right person at this time in Laura’s life.

The couple never married, even after Laura gave birth to a daughter, Jimmie D. Rebecca Padgett, on July 31, 1922. Hugh was acknowledged as the baby’s father on the birth certificate.

The baby’s life was cut short nine months after its birth when it swallowed an open safety pin, lacerating the baby’s stomach, while Laura was living in Palm Beach.

The fact that Laura had taken up with another man apparently did not bother John, as he and Laura soon reunited when John made his last escape on Sept. 27, 1923, from a road camp near Westville in Holmes County.

With deadly consequences, he would join Laura back in the Everglades to continue his life of crime.

NEXT IN THE SERIES (Part 7 of 10) 

Joe Ashley’s stills near the Ashley home
STATE OF FLORIDA ARCHIVE

Part 7, Tuesday, Oct. 29
SHOOTOUT AT THE STILL Deputies raid one of Joe Ashley’s stills near the Ashley home with deadly consequences for both the Ashleys and lawmen. Bob Baker takes over for his dad as sheriff and intensifies his search for John, who has made yet another escape from prison, and other members of the gang. (All-new digital release)

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