John Hopkin Ashley (March 19, 1888  – November 1, 1924) was an American outlaw, bank robber, bootlegger, and occasional pirate active in southern Florida during the 1910s and 1920s.

His gang robbed nearly $1 million from at least 40 banks while at the same time hijacking numerous shipments of illegal whiskey being smuggled into the state from the Bahamas.

His two-man raid on the West End in the Bahamas in 1924 marked the first time in over a century that American pirates had attacked a British Crown colony.

Ashley's activities also hindered Prohibition bootleggers in major cities, whose importation of foreign liquor undermined local moonshiners.

He was one of nine children born to Joe Ashley, a poor Florida woodsman, who made his living by fishing, hunting, and trapping otters.

According to fellow Seminole Jimmy Gopher, Ashley had been last seen with Tiger traveling in a canoe together with a boatload of otter hides to sell at a local market.

Authorities were later told by fur traders in Miami, the Girtman Brothers, that John Ashley had sold them the hides for $1,200;[1] the previous day he had also been arrested in West Palm Beach on a charge of "recklessly displaying firearms".

Two deputies, S.A. Barfield and Bob Hannon, found Ashley camping in a palmetto thicket near Hobe Sound and attempted to take him into custody.

John Ashley then sent the officers back with a message for Sheriff George B. Baker "not to send anymore chicken-hearted men with rifles or they are apt to get hurt".

[5] Ashley repeatedly escaped from various local jails and eluded law enforcement until he was gunned down at the St. Sebastian River bridge in Roseland.

[2][3] He was taken to Miami to stand trial for the murder of Tiger, however, the state's attorney believed that that had a better chance of prosecuting Ashley for the Stuart robberies in West Palm Beach.

Entering the jailer's house, Bob Ashley shot Deputy Sheriff Wilber W. Hendrickson at point-blank range[8][9] and left with his jail keys.

Each of the men claimed to not know how to drive the car either so Bob Ashley jumped on the running board of a passing truck and forced the driver, T.H.

[2][4][6][8][10] Angered by Bob's killing spree, several thousand Miami residents threatened the jailhouse and talked of lynching John Ashley in his cell.

We were in your city at the time one of our gang, young Bob Ashley, was brutally shot to death by your officers and now your town can expect to feel the result of it any hour.

Whenever she heard authorities were nearing one of Ashley's hideouts, she would drive her car through secret backwoods trails, often without headlights if at night, to warn fellow gang members.

[1][3] Ashley behaved as a model prisoner for two years until escaping from a road camp, with the assistance of fellow bank robber Tom Maddox, on March 31, 1918.

The Ashley gang continued moonshining in his absence, maintaining their many stills in the woods of central Florida, and began hijacking rum runners as well under Clarence Middleton or Roy Matthews.

[1][6][8] The circumstances surrounding Ashley's third and final escape remain a mystery, only that he "vanished from his cell", and returned to bank robbery with his gang.

In one of their more memorable robberies, the gang managed to rob the Stuart bank a second time in September 1923 after Ashley's teenage nephew Hanford Mobley sneaked into the building disguised as a woman and escaped with several thousand dollars.

[6] Shortly after the robbery, Mobley and Middleton were caught in Plant City and Matthews in Georgia, however all escaped and were back together in the woods near Gomez by the end of the year.

In 1924, he and his nephew Hanford Mobley stole a sea skiff and led a raid against rum-runners in the Bahamas' West End leaving with $8,000 from four wholesale liquor warehouses.

Suspecting that the law might be on to his plans, Ashley changed his route at the last minute and sailed through St. Lucie Inlet, narrowly avoiding capture.

Baker was determined to capture Ashley and, with weapons from the Florida National Guard and deputized civilians, made plans to surround the cabin and starve him out.

His father, Joe Ashley, was killed[6] in his bunk while his partner, Albert Miller, and Laura were seriously wounded by buckshot from a deputy's shotgun.

[1] On November 1, 1924, Baker received a tip from an anonymous source, believed to be a gang member's girlfriend (or a disgruntled brother-in-law),[1] that Ashley would be travelling up the coast on the Dixie Highway to rob a bank in Jacksonville.