Ashley Gang descendants not fond of ancestor

Then and now, the family of Ashley outlaw Ray Lynn has kept a distance

BY GREGORY ENNS

As the daughter of Ashley Gang outlaw Ray Lynn, Inez Lynn Hamilton had an unusual —and intentionally misleading — story that she would share with her grandchildren about her father’s death.

“She told us her father died when she was a child and had fallen off the Sebastian River bridge and had hit a rock,’’ said Hamilton’s granddaughter, Lee Ann Alderman of Fort Pierce.

Hamilton’s father was Jerold Ray “Shorty’’ Lynn, 25, who had just joined the notorious Ashley Gang after escaping from a state prison road crew in Marianna, Florida, on Aug. 11, 1924. Barely 90 days later, he and three others — fellow escapee Clarence Middleton, gang leader John Ashley, and Ashley’s 19-year-old nephew Hanford Mobley — would be shot to death in an ambush set up by lawmen at the Sebastian River bridge exactly 100 years ago on Nov. 1, 2024.

“I remember she didn’t like to talk about him a lot,” Lee Ann said. “It was an embarrassment for her. He was not a good man or a kind man.”

Lee Ann said her grandmother, Inez Lynn Hamilton, would recall a story of her father using her for his target practice. “We were told by her that he would put her out in the yard by a stump and shoot around the stump and try to scare her.” Lynn had also thrown her younger sister against a wall.

Born in Pike County, Alabama, Lynn had grown up in Milton in the Florida panhandle.  Lynn married Lillie Johns of Charlton, Georgia, in 1917 and for a time they had lived in Jacksonville. 

They had three young children, Inez [Hamilton], born in 1918, Lee [Kuzminski], born in 1919, and Ressie Lynn, born in 1921. It was a marriage interrupted by military service and a prison sentence. 

Lynn had served in the 40th Infantry Army in France in World War I, but went AWOL in 1919 when he landed in New York on his return to the United States, according to research conducted by Lee Ann Alderman’s son, Austin Alderman of Fort Pierce. In 1921, Lynn was sentenced to five years in prison on a grand larceny conviction in Jacksonville. 

At Raiford state prison, Lynn became friends with Ashley Gang member Clarence Middleton. Upon their escape, the two fled together to the Ashley headquarters in south Florida. Along with John Ashley and Joe Tracy, both men were suspects in the Sept. 12, 1924, robbery of the Bank of Pompano in which $5,000 cash and $4,000 in liberty bonds were taken.

MOVE TO FORT PIERCE 

Lillie Lynn moved with her three children to Fort Pierce in 1923, a move that brought her closer to family in Pompano. By coincidence, Ray Lynn’s body and the bodies of the other three would be brought to downtown Fort Pierce and displayed on the sidewalk Nov. 2, 1924. 

The Aldermans say Lillie had been estranged from Lynn by the time she moved to Fort Pierce from Macclenny, Fla., though they never divorced. Lillie Lynn later married Freeman Smith and her three children later used the Smith surname. Daughter Inez married Jesse Hamilton in 1935.

“She was a hard-working woman,” Lee Ann said of her grandmother, who ran a successful citrus business with her husband. “She didn’t want to be like her father. She worked for everything she had. She worked out in the groves and wanted to make something of herself, and she was successful in her own right.”

Neither Lee Ann, 58, nor Austin, 28, believes the Ashley Gang did good for others. “Around here, I feel that some people have a sort of a Robin Hood attitude toward them,” Lee Ann said. “I never had that same feeling because I heard stories about what he did to his daughter and other people that weren’t good. I never thought of them as Robin Hood-type good characters who were doing good, kind things.”

Austin Alderman said Lillie and her three children lived in poverty while Lynn apparently had plenty of money. He had $363 on him, worth about $6,500 today, when he was shot.  Lillie Lynn Smith died in 1976 and her daughter Inez Hamilton died in 1990.

Besides Ray Lynn, Austin Alderman has researched a more illustrious side of the family. His grandfather is the late Florida Supreme Court Justice James Alderman, scion of the early Florida cattle ranching family. Like his grandfather, Austin Alderman has also gone into law. He is a civil attorney at Dean Meade in Fort Pierce. 

“I have kind of a colorful story that I can tell people — that I live on the right side of the law, but let me tell you what my great-great grandfather did before me.”

EXECUTED?

Austin said he believes that Ray Lynn and the other three had been placed in handcuffs and executed that night at the Sebastian River bridge. 

“As an attorney,” Austin said, “I look at it objectively from a legal perspective. It was an extrajudicial killing by law enforcement.’’ 

A coroner’s jury had ruled at an inquest that the killings were justifiable homicide after deputies testified that the outlaws were not handcuffed. “I could look at it and understand perhaps why law enforcement at the time did what it did, not that it was right. John Ashley had escaped from prison three times, Clarence Middleton had escaped twice and Ray Lynn had escaped with Clarence Middleton. They were struggling to even keep them incarcerated.”

Austin Alderman said he has never been able to see Ray Lynn’s grave at the Ashley family cemetery in Fruita in southern Martin County. The cemetery is inside the private gated Mariner Sands residential subdivision, which was developed in the 1970s.

Lynn was buried at the Ashley family cemetery — the only non-family member so interred — after relatives refused to claim his body. Lynn’s parents, John and Minnie, had previously disowned him. The Ashley family took care of the burial because of his loyalty to the family. His body was placed in an above-ground vault between the bodies of John Ashley and Hanford Mobley, though because of grave robberies the exact location of his remains is not certain.

“His own family said he was dead to them,” Austin said. “They had no interest in claiming him. He wasn’t one of theirs because he was nothing but trouble.”