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Decades later, Ashley part of local lore

More than eight decades after he and his crime partners died in 1929, John Ashley continues to be one of the most intriguing figures in Florida history.

Many a relative of an Ashley Gang member has written to defend, or at least try to explain, the long-dead gangster.

Clyde Middleton wrote in January to tell us of his uncle, Clarence Middleton (pictured below):

middleton

“He was the second oldest son of Steven and Margeret Middleton, my grandparents. He had four brothers and three sisters living in Jacksonville; all are deceased now.

“His oldest brother, Jack, owned the Embassy Club and the Peacock Club in Jacksonville.

“Cecil, Clyde and Bruce all served honorably in World War II and became successful businessmen in Jacksonville after the war.

“Clarence probably got involved in rum running in the early ’20s and met up with some of the Ashley Gang in prison then fell in with them.

“He was one of the four men murdered on the San Sebastian bridge in 1924. He is buried beside his father in Jacksonville.”

Clyde refers, of course, to the evening of Nov. 1, 1924.

Deputies stopped Ashley and Middleton, along with Hanford Mobley and Ray “Shorty” Lynn, on a wooden bridge over the St. Sebastian River in what was then St. Lucie County.

They later said the men were shot trying to escape. But many believed they were assassinated by lawmen tired of being humiliated from Stuart to Miami by robberies, moonshining and murder.

In 1997, Ada Coats Williams, a retired teacher of creative writing at Fort Pierce’s Indian River State College, completed Florida’s Ashley Gang, the first book on the Ashleys since 1928.

A retired deputy who’d been on the bridge that night had confirmed to her in the 1950s that the men were shot while handcuffed, after John made a sudden move.

He had told her on the condition that she keep the secret until after all those involved had died.

Williams, profiled in this column in September on her 90th birthday, never has publicly identified her confidant.

ashleygangbook1
The Notorious Ashley Gang, by Hix Stuart, is a 1920s book about the infamous gang that terrorized South Florida in the early 20th century. (Palm Beach Post file photo)

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Posted in Eliot Kleinberg February 17, 2011 at 10:10 am.

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