
DEADLY CONSEQUENCES
Part 5 of 10
ANOTHER BANK ROBBERY

Three Ashley Gang members led by Hanford Mobley in drag pull off one of the gang’s biggest bank robberies but end up captured
BY GREGORY ENNS
Instead of dressing for court and appearing in Tampa to face a charge of piracy on May 2, 1922, Hanford Mobley slipped on a woman’s black dress and white blouse, stockings and high heels and large-brimmed veiled hat.
Clutching a handbag, he headed out with Clarence Middleton, 22, and Roy Matthews, 28, to rob the Bank of Stuart, the same bank Hanford’s uncles John and Bob and Kid Lowe had robbed seven years earlier.
Both Middleton and Matthews had been working bootlegging operations with Hanford. Middleton was the second oldest of seven children of Stephen and Margaret Middleton of Jacksonville. His father had died 15 months before. Middleton’s older brother, Jack, was the Florida heavyweight boxing champion.
Middleton, who also used the alias Jones, was somewhat bigger than Hanford and rough looking. At 5 feet, 7 inches and weighing 143 pounds, he had black hair and blue eyes, a fair complexion and several small scars on his face.
Matthews, who also went by Robert Matthews, was addicted to opiates and was “known to have an utter disregard of the law” and was fearless, said author Hix Stuart, who was marshal of Stuart at the time of the robbery and would later go on to write a book about the Ashleys. For the Bank of Stuart robbery, Matthews had blackened his face with burnt cork in an attempt to conceal his identity.

HOW IT WENT DOWN
According to newspaper accounts and Stuart’s The Notorious Ashley Gang, the Bank of Stuart robbery went like this:
With Middleton as a lookout waiting for them outside, Hanford and Matthews walked into the bank about 11:45 a.m. and ordered cashier Percy Fuge and assistant cashier Peter Hyer to hold up their hands and back away from the counter. Hanford’s disguise apparently didn’t work as Fuge immediately recognized him, as did another employee, John Taylor.
Hanford headed toward the bank’s vault and ordered the employees to lie down on the floor while Middleton entered the bank and cleaned out the cash drawers at the teller windows. Hyer was ordered to pick up silver that had been strewn about on the floor, with the money placed in a sheet or suitcase. Meanwhile, Hanford entered the vault, took out several bundles of cash and then at gunpoint ordered Fuge to open another time vault.
Without Hanford seeing, Fuge turned a time lock so that the vault wouldn’t open. Meanwhile, B.H. Anderson, a local barber, entered the bank to make a transaction but tried to leave when he saw the men wielding guns. As Anderson tried to leave, Middleton jumped out of the car, drew a revolver and ordered Anderson back inside. The commotion apparently frightened Hanford and Middleton, and they headed toward the car and fled with $8,133.14 in currency and loose silver.
The robbers then headed north on Dixie Highway to White City then west toward Okeechobee Road, where about a mile west of Fort Pierce they exchanged the stolen Buick for a stolen Ford.

THE CHASE IS ON
Marshal Stuart, who had heard cashier Fuge yell that the bank had been robbed, took chase until reaching the abandoned Buick. Palm Beach County Sheriff Bob Baker had caught up with Stuart and took the trail from there. When Stuart took possession of the Buick to return it to its owner, he discovered the woman’s clothing Hanford was wearing. Two bottles of whiskey also were inside.
Meanwhile, Baker and a posse of five other deputies kept on the trail across the state in driving rain.
The Buick had been stolen from a Palm Beach taxi driver who had been hired to transport them the night before. As daylight approached, the gang tied the driver to a tree and gagged him near Gomez and stole $30 from him.
Law authorities said the Ford, the vehicle placed in Fort Pierce for the transfer from the Buick, was stolen from D.J. Smith of West Palm Beach, a relative of Hanford.
Hanford and Middleton registered at a hotel in Plant City, but drew suspicion from the proprietor, who called the town’s marshal. The two then headed to Lakeland, where they were captured at the train depot by a motorcycle policeman who had received a bulletin to be on the lookout for them.
The Ford had apparently been in a collision, as Baker found part of a fender torn loose. Later, at a grocery store, Baker learned that the two had inquired about the best way to get to Savannah without going through Jacksonville and were told that they could get a train out of Plant City, a tip that prompted Baker to alert Plant City law authorities.
A Lakeland motorcycle policeman and Plant City policeman, W.B. Dormany, headed to the Plant City depot where they encountered Middleton and Hanford, who reached for their guns but were overpowered. They had with them a bag of silver worth $2,335.05 of the total $8,133.14 take.
MATTHEWS STAYS FREE
Meanwhile, Matthews had gone to a store to get cigarettes. When he returned, he later told authorities, he saw his friends in the custody of officers. He then slipped around the station and boarded a train that was pulling out for Jacksonville.
After his arrest, Hanford said in an interview with Baker that the robbery was planned by two other men who met them in Fort Pierce, driving them away and letting them have $2,335 in silver. He said the plan was to later meet in Savannah, Georgia, to divvy up the stolen money. When Baker pressed Hanford for information about Matthews, Hanford cursed the sheriff and “stated his uncle had never squealed and he did not intend to do so either,” according to Stuart’s book.
Both Hanford and Middleton had tickets for Savannah when they were arrested at the Plant City train depot. Hanford also claimed that Matthews had held him up with a revolver and taken the money from him.
PRISONER TRANSPORT
Transporting the prisoners, Baker was accompanied by deputies Joe Padgett and John Gainer. Their car broke down in Kissimmee, forcing them to lodge their prisoners in the jail there. “The burning of the car’s bearings proved to be a blessing to Sheriff Baker, for in passing through Fort Pierce the following morning he learned that the Ashley Gang had been in ambush all night, awaiting the officers, intending to take the prisoners,’’ Stuart wrote. St. Lucie Sheriff Augustus Ruffner had approached the ambush several hours before the prisoners were to pass through Fort Pierce, but Ashley Gang members took flight.
According to Stuart’s narrative:
Hanford and Middleton were placed in the Palm Beach County Jail. Stuart said Middleton made a complete confession to Baker there but begged that he not tell Hanford for fear that Hanford would kill him.
In his search for Matthews, Baker then headed to Jacksonville, where he learned Matthews had paid cash for a new car and had made deposits at two banks. Checking the post office and telegram office, Baker and a Jacksonville detective learned of a bouquet of flowers that had been sent to a woman from Matthews, who had placed the order from Savannah, Georgia. They headed to Savannah but learned upon arrival that Matthews had left that morning. They headed to Atlanta, where his mother lived.
But in the end, Matthews was arrested in Griffin, Georgia, after being pulled over for not having a proper tag for his car. When the car was searched, several cases of liquor were discovered.
Baker claimed that Matthews gave a full confession, telling him that he didn’t go in the bank until the barber entered. He said Hanford Mobley had planned the robbery a week earlier. Matthews said he received $2,300 for his participation in the robbery, and Baker said he had $818 left when he arrested him. Matthews apparently was initially identified by an alias, Sam Williams.
A judge later set bail of $15,000 for Hanford and Middleton and $10,000 for Matthews, who was identified as aiding authorities in the case. During a preliminary hearing May 30, 1922, Hyer, the bank employee positively identified Matthews, who also was known as Robert. He said he had known Hanford for about eight months. But when pressed to make a positive identification of Hanford, he said he could not because it was impossible to see through a veil the face of the person wearing the women’s clothing.
WAITING FOR TRIAL
Unable to make bail, the three would learn later that summer that because of a heavy case load their trial wouldn’t be scheduled until early 1923. The judge overseeing their case also ordered them transferred from the Palm Beach County Jail, which was being renovated, to the Broward County Jail in Fort Lauderdale.
Said a Palm Beach Post article of their nonchalant manner at the time they were ordered transferred: “They seemed altogether at ease and during the intervals in the court procedure chatted and laughed with relatives and friends.’’
Their defense would rest largely on alibis.
Hanford’s sister, Laeto, was scheduled to testify that Hanford was with her in West Palm Beach at the time of the holdup. Two Jacksonville men, Harry Burns and B.W. Paul, were scheduled to testify that Matthews was with them in the Jacksonville area at the time of the robbery. Middleton would later claim that he was in Avon Park on the day of the robbery.
But Hanford and Matthews never went to trial. On Dec. 14, 1923, they escaped from the Fort Lauderdale jail. The two men forced their way through a skylight leading to the roof and then reached the ground with the aid of blankets and sheets tied together.
Middleton, also being held with them, decided not to participate and told deputies the escape had been planned for weeks.
MORE CRIMES
After his escape, Hanford remained in South Florida, apparently with Matthews, going in and out of the Everglades.
A little more than a month after the escape, on Jan. 24, 1923, a boy fitting Hanford’s description was suspected of leading a trio that held up W.H. Brooks, a 70-year-old tourist from Baltimore, on the Dixie Highway between Hallandale and Hollywood. The three took Brooks’ seven-passenger Buick, $796 in cash, about $450 in jewelry and a .38 caliber Smith & Wesson revolver. Brooks identified Hanford in a photo as the boy who pointed a revolver at him.
Brooks said he was in the woods trying to camp for the night when two men with revolvers went through his clothes, took his wallet a diamond stickpin, two diamond rings, a diamond cuff link, money and a .38 caliber Smith & Wesson revolver.
Hanford was also suspected in a Jan. 31 theft of an Essex touring car and robbery by three boys. The car was recovered. The victims were S.R. Johnson and Dr. S.A. Folsom of Atlanta. Johnson was robbed of his watch and $100 in cash. They stopped when they saw a handbag on the Dixie Highway in Dade County.
ANOTHER PRISON, ANOTHER ESCAPE
As Matthews and Hanford remained free, Middleton was tried in March 1923 and found guilty of aiding in the Bank of Stuart robbery. Middleton’s defense was that he was in Avon Park at the time of the robbery. He was sentenced to 10 years of hard labor by Judge E.C. Davis.
At Raiford prison, Middleton met fellow inmate Ray Lynn, 23, who was serving a five-year sentence for a grand larceny conviction in Duvall County in 1921. Lynn, a married father of three young children, had served in the Army in France during World War I but went AWOL on returning to the states.
Middleton also likely knew another inmate, Joe Tracy, doing a two-year stretch for highway robbery, who would also become a member of the Ashley Gang. The 30-year-old Tracy, who grew up in Crab Grass in Osceola County, also had a family connection. Tracy’s brother, Walter, had married the mother of Laura Upthegrove, John Ashley’s girlfriend.
Apparently, the gang had a standard for bravery and Tracy didn’t always meet John Ashley’s standards. “Let me tell you something about Joe Tracy,” outlaw Heywood Register, who was sometimes associated with the gang, said in a 1925 interview. “He’s a bold, bad outlaw but a coward. John Ashley nearly killed him several times.”
Lynn and Middleton later were assigned to state road camp No. 1 in Marianna, Florida, in the Panhandle near the Alabama state line when they escaped on Aug. 11, 1924. Tracy had been released from prison after serving his sentence just a week earlier, on Aug. 3, 1924, and it was widely believed that he had picked them up in a Ford car recently purchased from one of the guards at the prison.
In the next three months, they would meet up with John Ashley in the Everglades, help him rob the Bank of Pompano and meet their doom at the Sebastian River bridge.
NEXT IN THE SERIES (Part 6 of 10)

Part 6, Monday, Oct. 28
THE LOVE INTEREST — Laura Upthegrove, a married mother of four, joins the gang and becomes John’s partner in crime and romance. (All-new digital release)
