The Ashley Gang
When the first Sheriff of Palm Beach County, George Baker died in 1920, his son Robert succeeded him as sheriff. Robert C. (“Bob”) Baker helped bring the notorious Ashley gang to justice, outlaws who had terrorized southeast Florida for 13 years. Members included brothers John and Bob Ashley, their nephew Hanford Mobley, and two men named Middleton and Lynn.
The gang robbed banks and trains, ran rum from the Bahamas during Prohibition (1920-1933), and murdered people. Wilbur Warren Hendrickson, deputy and jailor in Miami, was killed in 1915 by Bob Ashley during the attempted rescue of his brother John. In November 1924, Baker helped organize a trap at which Ashley, Mobley, Middleton, and Lynn were killed. Laura Upthegrove, John Ashley’s girlfriend, committed suicide.
Dr. Anna Darrow, who came from Chicago to practice medicine and run a pharmacy in the Glades from 1912 to 1922, wrote about the challenges of those years, including the Ashleys in an article entitled “Reminiscences of the Lake Okeechobee Area, 1912-1922” for Tequesta in 1967:
Historians told us that the early pioneers of the Everglades were outlaws and hid in the wilderness to be lost from civilization. Sometimes when filling out a birth certificate and I asked where the parents were born, the answer would be to write “unknown” and not to ask any more questions. I was called upon to take care of the Ashleys, the Mobleys, the Rice gang, and the Upthegroves. Leland Rice had his lower jaw shot off and was carried to our house in the middle of the night. … When I treated Laura Upthegrove, who lived on the ridge near Pahokee, I didn't know that she was in with the outlaws.