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Sheriff Bob Baker and the Ashley Gang

June 01, 2023

By David Brand 
Law Enforcement Coordinator, Florida Sheriffs Association

In the early 1900s Florida, father and son sheriffs chased a gang of bootleggers, robbers and murderers from deep in the Everglades to what would later become known as the Gold Coast of Florida resulting in what would become a blood feud between the two families.

George B. Baker hailed from Hamilton County, Florida, and moved to Palm Beach County, then Dade County, in 1901. With an interest in politics, George became a mayor and member of the Dade County Commission.  When the Florida legislature carved Palm Beach County out of Dade County in 1909, Governor Albert W. Gilchrist appointed George the sheriff of the fledgling new county. George became a popular sheriff and was continuously elected until his death in 1920. Upon his death, Governor Sidney J. Catts appointed Bob Baker, George’s son and deputy to replace him.

Sheriff George Baker, Palm Beach County

Ten years earlier, Deputy Bob Baker, then a 23-year-old deputy, went to arrest a man named Wash Pope who was armed with a shotgun. The suspect fired at Bob and nearly blew his right leg off. A doctor amputated his leg above the knee with him eventually receiving an artificial leg. Considered a progressive lawman, establishing fingerprint units and contemporary methods, he was reelected each term until his death in 1933.

Sheriff Bob Baker, Palm Beach County

The Ashley Gang 

John Ashley, who later became known as the “Swamp Bandit,” first came to the attention of Palm Beach County Sheriff George Baker in 1911. John was an otter trapper who sometimes partnered with Desoto Tiger, the son of Tom Tiger, a well-known leader of the Seminole Tribe. The two men had been trapping in the Everglades when Ashley came into town alone. Several days later, Desoto Tiger’s body was uncovered while work crews were dredging a canal from Ft. Lauderdale to Okeechobee. Ashley sold the otter hides to a dealer in Miami for the Sizable sum of $1,200.00. Another member of the Seminole Nation told the sheriff that Ashley was the last man seen with Desoto Tiger.

Sheriff George Baker sent two deputies to the Gomez area, south of Stuart, to arrest Ashley. It should be noted that Martin County was not created from Palm Beach County by the legislature until 1915. John and his brother, Bob Ashley, ambushed the deputies and told them to go back and tell the sheriff “not to send any more chicken-hearted men or they might get hurt.”

The Feud Begins 

Ashley left the state, when he was going to be arrested for the murder of Desoto Tiger, but later returned and surrendered. His trial ended in a mistrial, possibly because the Ashley family was well-known in the area. The State Attorney requested a change of venue to Miami. Upon hearing that, Ashley broke away from his jailer, Deputy Robert C. “Bob” Baker, the sheriff’s son, and fled deep into the Everglades.

By 1915, a mobster from Chicago named Kid Lowe joined the gang and taught John about robbing trains with the two robbing a passenger train early that same year. Also, two more members joined the gang around the same time: John Clarence Middleton and Roy Young Matthews.

Roy Young Matthews

On February 23, 1915, Ashley and his gang held up a bank in Stuart, Florida. Reports of what they stole are varied with one account being $4,300.00 and another being $45,000.00 in silver and cash. Stories about what occurred during the getaway vary as well. One version has Kid Lowe accidentally firing his gun, striking John in the right jaw with the bullet lodging in his left eye causing him to lose the eye. Another version involves an argument about splitting up the cash. In pain and needing medical treatment, Ashley was soon arrested by Sheriff George Baker. He was left with an eye patch and eventually received a glass eye.

According to one account, between 1915 and 1924 the gang robbed over forty banks.  In 1914, the Pioneer Era in Palm Beach County had ended only 20 years earlier. Many of the free-spirited settlers who remained knew each other and were not especially fond of the bankers and wealthy landowners. Many of them respected John Ashley who gave money and food to those in need making him a sort of Florida cracker Robin Hood.

Once in custody, Ashley was subject to two trials. One for the 1911 murder and another for the 1915 bank robbery. He was convicted of the murder but in a strange twist, the Florida Supreme Court reversed the decision. He was convicted and sentenced for the bank robbery.

Ashley was determined to once again disappear into the Everglades and get back to the family business of robbery and moonshining. While in jail in Miami, awaiting trial for the second time on the murder charge, Ashley attempted an escape by digging a hole in the cement floor of his cell with a tablespoon. He succeeded in digging a twelve-foot tunnel under the floor while disposing of the dirt and debris by flushing it away and covering the hole during the day with a rug. However, unlike the character Andy Dufresne in the movie The Shawshank Redemption, the jailers found the tunnel.

While in the Dade County jail, rumors began circulating that his family was going to break him out. This included Joe Ashley, John’s father, brothers Bill, Ed, Frank, and Bob along with Laura Upthegrove, John’s girlfriend and reported getaway driver who was later known as the “Queen of the Everglades.” Bob Ashley, apparently tired of waiting on the others to get organized, attempted to free John by himself.

Laura Upthegrove

On June 2, 1915, Bob Ashley went to the deputy sheriff’s residence, which adjoined the Dade County jail and knocked on the door. When Deputy Wilber Hendrickson opened the door Bob shot him in the chest and took his jail keys from him.  Ashley fled the scene, dropping the keys. Trying to escape, he stopped a passing truck and threatened the driver. The driver deliberately stalled the truck allowing Officer John R. Riblett, of the Miami Police Department, to demand that Ashley give up. Ashley shot him in the head. The officer returned fire resulting in both Ashley and the officer being killed. Officers took both Ashley and Officer Riblett to a hospital where they were both pronounced dead. Miami had lost its first police officer killed in action.

Deputy Wilber Hendrickson, Dade County 

On November 23, 1916, John Ashley pleaded guilty to robbery and was sentenced to 17 years in the state penitentiary at Raiford in north Florida.  After being transferred to a road work camp in the Florida panhandle, he escaped and once again disappeared into the Everglades.

Rum Running in the Florida straits 

1920 brought Prohibition and a new illegal industry was born. Al Capone might have controlled alcohol in Chicago but rum runners supplied Florida. Suddenly, the Ashley boys had a new job. During John’s absence in prison, the gang once again began moonshining but now also hijacking rum runners.  John, along with brothers Ed and Frank, ran liquor across the Florida Straits from British warehouses in the Bahamas and Bimini.  However, they proved to be inept at this new endeavor. In July 1920, Joe (the father) and Bill Ashley were arrested in Highlands County for bootlegging. John Ashley was captured in July 1921, making liquor deliveries in Wauchula in Hardee County. The same year, Ed and Frank Ashley were lost at sea making a run to Bimini.

Different members of the gang, now in remnants, robbed a bank in Stuart in December 1923. One member, Hanford Mobley, wore a dress and veil around his face to conceal his identity. Sheriff Baker tracked Mobley and co-conspirators to Plant City near Tampa where they were captured and brought back to the West Palm Beach jail. The sheriff then had them transferred to the jail in Ft. Lauderdale where they escaped a few weeks later.

Hanford Mobley

One of the co-conspirators, John Clarence Middleton, refused to break out and was sent to Raiford prison. While in Raiford, Middleton along with John Ashley, who was already there, and another inmate named Ray “Shorty” Lynn, escaped again and went back into the Everglades to moonshine once again.

On September 12, 1924, the gang robbed the Pompano Bank in Broward County stealing $23,000.00. John Ashley, again, sent Sheriff Baker another bullet and a message stating that this was “in case the sheriff ever gets out to the Glades.”

The Last Straw  

This latest escapade proved to be too much for Sheriff Baker. He borrowed rifles, machine guns and ammunition from the National Guard, deputized citizens, and formed an old-fashioned posse. He put Deputy Fred Baker, his cousin, in charge of the posse and they went to Ashley’s moonshine still close to the small village of Fruta. On September 29, 1924, they raided the camp. Gunfire was exchanged. Joe “Pa” Ashley was killed along with Deputy Fred Baker. Laura Upthegrove received buckshot to the knee and was captured. John Ashley, along with several confederates, managed to escape.

Saddened by the death of his father, John, along with the remaining members of the gang, stole a car and made plans to drive up the Dixie Highway, later named U.S. 1, to Jacksonville. Somehow, Sheriff Baker learned of not only the escape route but the date and description of the stolen vehicle. Some historians believe that Laura Upthegrove, scorned from being left out of the flee from the area, tipped off the sheriff.

Laura Upthegrove and John Ashley

Knowing that the gang had informers in the area, Sheriff Baker planned on capturing them on the Sebastian River bridge, north of Ft. Pierce. Sheriff Baker sent Chief Deputy H. L. Stubbs, along with deputies Elmer Padgett, I.B. Thomas, and the Stuart Town Marshal O.B. Padgett to inform St. Lucie County Sheriff J.R. Merritt of the plan to capture the gang. Sheriff Merritt, now in charge, added his Chief Deputy C.E. Wiggins, and Ft. Pierce chief of Police J.M. Smith to the detail.

The End of the Feud 

On October 31st, the officers drove to a wooden bridge that crossed the Sebastian River. After crossing over into Brevard County, they hid their vehicles and walked back across the bridge. A chain was suspended across the entrance to the bridge and a red lantern was attached to it. Before the gang arrived, two local men, Ted Miller and T. O. Davis, drove up to the chain and stopped, making them witnesses to the arrest.

Ashley, Mobley, Middleford and Lynn arrived at the bridge and stopped at the chain. When the lawmen emerged from the woods, Ashley reached for a rifle but Sheriff Merritt and Chief Deputy Wiggins interceded. The gang members were then removed from the vehicle. At this point, the sequence of events becomes lost to history. Some testimony indicated that the gang members were being handcuffed but other testimony suggested that the gang members reached for pistols that were concealed. Regardless, in the confusion all four gang members were shot and killed by the officers similar to the ambush of Clyde Barrow and Bonnie Parker in Louisiana in 1934. All four bodies were loaded up in the stolen car, taken to Ft. Pierce, and laid out in front of W.I. Fee’s Funeral Home; a common practice at the time. John Hopkins Ashley lay dead at age 36 ending the feud with the Bakers.  Sheriff Bob Baker removed the glass eye from John and boasted that he would make a key fob out of it but later returned it to the family.

John Ashley’s glass eye that is displayed in the Martin County Historical Society museum

John Ashley’s grave

The court ruled the killings justifiable. An editorial published in The Jacksonville Florida Times-Union on November 5, 1924, summarized “the extinction of the Ashley gang by the summary means employed…will call forth no sympathy, but, rather there will be freer breathing because those outlaws no more will strike terror to the hearts of innocent people, no more will molest, rob, and murder, as was their practice…Too much credit cannot be given the officers’ display of vigilance and bravery.”


Laura Beatrice Upthegrove Swindal, after the death of John, moved around and eventually settled on her family’s homestead on the eastern shore of Lake Okeechobee where she was in and out of jail for liquor violations. In August 1927, while selling beverages from a small family store, she became involved in an argument with a customer over a liquor sale. Laura produced a gun that was taken away by her mother. She then went inside and drank a bottle of Lyson. Within a few minutes, her sad life was over.

In 1973, a movie entitled “Little Laura and Big John” was produced about the exploits of John and Laura. It was billed as “the desperate love between two people destined for destruction.” The tagline was “They’ll steal into your heart – then shoot their way out!” Filmed in Stuart, Florida with many of the extras being local residents.

Movie Poster

Sheriff Bob Baker never revealed his source.


Click on the link below for a YouTube video about finding Ashley gang artifacts in Fruta, Florida:

Click on the link below for a YouTube video from the Historical Society of Martin County about the Ashley gang:
1  Rogers, William & Denham, Mike A look back in Florida Sheriff History: Palm Beach County Sheriff Bab Baker vs. the Notorious Ashley Gang. The Sheriffs Star  May/June 2000 p. 4
2 Procyk, Richard “The Ashley Gang and Frontier Justice”  History: Town of Jupiter  December 2, 2012
3  Ibid
6  Ling, Sally J. Run the rum In: South Florida During Prohibition. The History Press  Charleston, South Carolina  2007 pg 87, 89, 91.
7  McGoun, William E. Southeast Florida Pioneers: The Palm and Treasure Coasts. The Pineapple Press  Sarasota 1998 pg 136-140.
8  ibid
9  Procyk, Richard History Tojwn of Jupiter December 3, 2012
10  Rogers, William & Denham, Make A look back in Florida History: Palm Beach County Sheriff bob Baker vs the Notorious Ashley Gang. The Sheriffs Star  July/August 2000 p.4
11  Rogers, William & Denham, Mike Florida Sheriffs: A History 1821-1945 Sentry Press, Tallahassee, Florida 2001 pg. 228.