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The Ashley Gang: Stuart's Bank Robberies, Rum-Running and a Deadly End on the Sebastian River Bridge

By The Led Zeppelin Bus · · 6 min read · 1,103 words

A public, expanded version of a newsletter article.

A century ago, the Ashley Gang robbed banks, ran liquor and killed lawmen across South Florida. Stuart was at the center of the story. Here is what the record shows, where the sources disagree, and where to see the history today. This is not a story about heroes. People were robbed, wounded and killed.

Colored pencil sketch of a 1920s downtown Stuart street corner with a small brick bank building and a Model T parked out front
AI-generated image Illustration (artist's sketch, not a photo)

The family in Fruita

Joe Ashley and his wife, Lugenia, raised five boys and four girls on a homestead at Fruita, between Stuart and Hobe Sound (Stuart Magazine). Fruita was part of the old Spanish land grant called Gomez. The family's land on the west side of Old Dixie Highway, including the family cemetery, was bought in 1978 to develop the Mariner Sands community (Indian River Magazine). Martin County didn't exist yet; until 1925 this was Palm Beach County (TCPalm).

TCPalm lists five gang members active between 1915 and 1924: John Ashley, Ray Lynn, Roy Matthews, Clarence Middleton and Hanford Mobley, John's nephew.

Black-and-white composite portrait of Ashley Gang members, published in 1928
Composite portrait of the Ashley Gang, as published in 1928; the center couple was reportedly paid to pose. Photo: State Archives of Florida, Florida Memory

View this photo at Florida Memory

The feud with the Baker sheriffs

The Town of Jupiter's history account says the feud began in 1911. Palm Beach Sheriff George B. Baker sent deputies to arrest John Ashley in the killing of Desoto Tiger, a Seminole trapping partner, and John and his brother Bob ran them off. The same account says Robert C. "Bob" Baker succeeded his father as sheriff in 1920 and kept up the pursuit (Town of Jupiter, "The Ashley Gang and Frontier Justice"). The Florida Sheriffs Association also covers the Bob Baker years (FSA). Sources differ: the Historical Society of Martin County exhibit page describes a "near 13-year feud with Palm Beach County Sheriff George B. Baker" (HSMC). Both father and son were sheriffs during the feud.

The Bank of Stuart robberies

The bank building still stands at 301 SW St. Lucie Ave., at the corner of Osceola Street in downtown Stuart (TCPalm).

  • 1915: John Ashley, his brother Bob and Kid Lowe robbed the Bank of Stuart. The Jupiter account dates it Feb. 23, 1915. As they left, a shot fired by Lowe hit John in the jaw and cost him the sight in one eye; he later wore a glass eye. Sources differ on the take: about $4,500 (TCPalm), $4,300 (Town of Jupiter), and "more than $4,200" (Palm Beach Post).
  • 1922: While John was in prison, Hanford Mobley, Clarence Middleton and Roy Matthews robbed the same bank. Instead of appearing in court in Tampa on a piracy charge on May 2, 1922, Mobley put on a woman's black dress, white blouse, stockings, high heels and a large-brimmed veiled hat. Bank employees recognized him right away (Indian River Magazine, "Another Bank Robbery"). TCPalm dates this robbery May 12, 1922.

Sources differ on the date: the Town of Jupiter account places the Mobley disguise robbery in September 1924. The 2024 newspaper and magazine accounts say 1922. We use 1922 and flag the conflict.

Black-and-white portrait photo of Hanford Mobley
Hanford Mobley. Photo: State Archives of Florida, Florida Memory

View this photo at Florida Memory

The gang was also blamed for a September 1924 robbery of the Bank of Pompano; the city's history page notes the crime "was supposed to have been committed by the Ashley gang" (Pompano Beach).

Rum-running and the sea

During Prohibition, the family ran liquor from West End in the Bahamas to hideouts south of Stuart (Town of Jupiter). John was arrested in 1921 delivering liquor near Wauchula. That year his brothers Ed and Frank Ashley vanished at sea on a run to Bimini. Sources differ on the month: the Jupiter account says October 1921; the headstones at the family cemetery read "Lost at sea - Dec. 1921" (Find a Grave).

In 1924, John Ashley and Hanford Mobley raided liquor warehouses at West End, Grand Bahama. The Historical Society of Martin County calls it a "two-man raid" (HSMC; also Wikipedia)).

The cost in lives

The violence was real. The Palm Beach Post reports the gang had killed three officers by the end. In 1915, Bob Ashley shot and killed Deputy Wilber Hendrickson in Miami while trying to free John; Bob himself died soon after. In early 1924, a raid on Joe Ashley's camp left both Joe Ashley and Deputy Fred Baker, the sheriff's cousin, dead (Town of Jupiter).

The end at the Sebastian River Bridge

On Nov. 1, 1924, deputies from St. Lucie and Palm Beach counties stopped John Ashley, Hanford Mobley, Ray Lynn and Clarence Middleton at the old wooden bridge over the Sebastian River in Roseland. All four were killed (TCPalm; Indian River Magazine, "Deadly End").

Accounts conflict. Officers said at the time they fired when Ashley reached for a weapon; witnesses said the men may have been shot while handcuffed (TCPalm timeline). Historian Ada Coats Williams later published a deputy's account, held until all the deputies had died, that the men were handcuffed when the shooting began (TCPalm). No one was charged. A historical marker stands at U.S. 1 and North Indian River Drive.

Where they rest, and where to learn more

John Ashley, Hanford Mobley and Ray Lynn were buried Nov. 4, 1924, behind what is now the Mariner Sands Chapel (TCPalm). The family plot, now called Ashley Park, was heavily vandalized over the years; the developer restored it and set new headstones around 1987 (Find a Grave; Martin County Genealogical Society). It sits on private property; visitors need the Mariner Sands property owners' association's permission.

The Historical Society of Martin County runs a permanent Ashley Gang exhibit at the Elliott Museum, 825 NE Ocean Blvd., Stuart, included with regular admission. Artifacts include John Ashley's glass eye, the original Bank of Stuart sign and a Prohibition-era still (HSMC; Joe Capozzi).

Some legends credit the gang with dozens of robberies; the exhibit's own page repeats a claim of "nearly $1 million from at least 40 banks," while Stuart Magazine notes there are only three known bank robberies the gang carried out. We report only the documented ones.

Sources

Every fact above comes from one of these sources, read Oct 20, 2026. Details may have changed since.

Drafted Oct 20, 2026 for Issue 1003. Spotted an error? Email asadigitalart000@gmail.com and we will fix it.

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