SEPTEMBER SEARCH

A distracted Bob Baker begins an intensive — and unsuccessful — search for the Ashley Gang after the Bank of Pompano robbery

BY GREGORY ENNS

Palm Beach County Sheriff Bob Baker got something of a break when John Ashley and the gang robbed the Bank of Pompano on Sept. 12, 1924.

While other Ashley Gang heists such as a train robbery and two bank robberies had been committed in Palm Beach County, the Bank of Pompano robbery was committed in Broward County, a jurisdiction beyond Baker’s responsibility.

Since late December 1911 when John killed Seminole DeSoto Tiger, Baker, and his father George before him, had been ridiculed about their inability to capture and keep John Ashley and the gang in jail or to bring them fully to justice for the crimes they committed. Throughout most of these dozen years, Ashley family patriarch Joe ran one of the biggest moonshine and bootlegging operations in southeast Florida right under the nose of the Bakers.

Which begs the questions.

Why was it so difficult for the father and son to capture and keep John Ashley? Why was the Ashley moonshine operation allowed to run so long without the weight of the law bearing down on it? Until 1923, all moonshine arrests relating to the Ashleys occurred outside Palm Beach County.

A FEW REASONS

John’s intelligence and guile certainly played a part in evading the Bakers. So did his decision to use much of the Everglades as a hideout when the heat of the law was on him. He was able to keep a base in Fruita, then in Palm Beach County but now part of southern Martin County, because it was a remote wilderness that provided plenty of cover for sharpshooter John. Lawmen walking into the woods in search of John could easily be ambushed and killed.

But the corrupt activities — and distractions — of both Bakers also could have played a role.

George Baker, who became sheriff of newly created Palm Beach County in 1909, was heavily involved in Bradley’s Beach Club, a gambling operation headed by Edward R. Bradley. In 1913, a group called the Law and Order League alleged that Baker was covering up the illegal activities of the club. Baker was also a leader in the local Ku Klux Klan.

 PROBLEMS AT HOME

Bob Baker, who was appointed sheriff on his father’s death in 1920 and soon won election, faced his own bootlegging problems when he was suspended from office March 22, 1923, by Gov. Cary Hardie after two federal indictments charged him with conspiring with bootleggers to violate prohibition laws. The Florida Senate refused to uphold the suspension after one of the indictments had been quashed, and he was returned to office May 14, 1923.

Baker also had problems at home that came to a boiling point as he approached re-election in November 1924 and pressure increased for him to capture John and the other members of the gang.

Things were getting so bad with Baker and his wife, Anna Etteene, at their Gardenia Street home that Baker would soon move out of the family home and file for divorce. Among other things, Baker alleged that his wife became “violently jealous’’ when he talked to women during the course of his duties and then confronted the women, accusing them of having improper relations with Baker. 

Baker said at one point Anna threatened him with a gun and bit him to the bone, and “blood flowed freely.” He said their marital arguments often occurred in front of their three children.

SORDID ACCUSATIONS

In court papers seeking support from Baker, Anna and her attorneys didn’t mince words about what she thought of her future ex-husband. Anna’s response, on file at the Historical Society of Palm Beach County, along with the complete Baker divorce file, alleges:

It is impossible for the human mind to be able to conceive how it can be that a man who knows and realizes in the smallest degree that there is no one of worse morals than he witnesses; that he is a very hard drinker and a drunkard, that he is a constant gambler, and a whoremaster of the worst type, and that he has had as his dearest companions the vilest and lowest down characters both male and female, and he not only knows that respondent knows these traits of his character, but that the public knows as well the same facts and that he only expects and hopes to maintain his character and cover up and conceal from the Court records these facts by virtue of his position as sheriff backed by his horde of deputies, supplemented by his great worth in a financial way, he being worth, as respondent believes and she has about as good a right to know as anyone … at least $1,500,000.

That sum would be worth about $17.7 million in today’s dollars.

PAYING ‘FINES’

Anna alleged that one way her husband built his net worth was through charging rum runners and moonshiners a monthly fee — disguised as a fine — for protection against being arrested for their misdeeds.

 Several witnesses in the divorce trial testified to paying the “fines’’ and bringing them to Baker’s house — instead of the courthouse — and giving them to Anna. One, a man named James Booker, said he would visit Baker’s home monthly, delivering $25 each time in a sealed envelope.

Whether Bob Baker had such an arrangement with the Ashleys is unknown and probably unlikely. But Baker’s arrangements certainly would have constrained him from cracking down on a high-profile target such as the Ashleys for fear that his secret protection of others would become public.

Anna Baker also alleged that her husband’s drinking had gotten to such a point that he sometimes suffered severe alcohol withdrawal symptoms known as the delirious tremens. In one instance, she said her husband’s alcohol use left him out of commission for a week.

This was occurring as the battle with John Ashley was intensifying, with John taunting Baker and leaving the message with two people that Baker could find him in the Everglades. John had returned to Florida after fleeing to California following Joe’s shooting death at his still Jan. 9, 1924, returning to avenge his father’s death. Now, the battle between John and lawmen was a deadly zero-sum game, and only one side could be the winner.

SEARCH CONTINUES

While the Bank of Pompano robbery occurred in Broward County, John and the gang appeared headed back to Palm Beach County when they ditched their get-away car and swam across the Hillsboro Canal and into the safety of the Everglades.

Unsuccessful at finding the gang immediately after the robbery and facing re-election in barely a month, Baker on Sept. 29, 1924, embarked on a well-publicized weeklong search. It was prompted by a tip he received that John, and the gang, were at Salerno and were planning to dash to Bimini or Gun Key to pirate ships that were harbored there.

That same day, a scout for the sheriff found the gang’s 26-foot cabin cruiser tied to C.C. Jacobs’ dock. It was loaded with mattresses and provisions that could last for months, including ten sides of bacon, preserves and dried fruit, 200 gallons of gasoline stored in drums and about $200 worth of ammunition. Baker confiscated the boat, which had been likely used as a source of supplies, as well as a coupe that was nearby.

Could the boat have belonged to Laura Upthegrove? Laura had established a lucrative rum-running business and at about that time was living in a second-floor apartment with her mother in Salerno, according to an interview her brother, Woody Upthegrove, had with historian Steve Carr in the late 1980s. She also had a boat about that size and was photographed in front of it, complete with what appeared to be whiskey cases in the background. 

Laura had recently been released on $2,500 bail in the murder of Deputy Fred Baker, the sheriff’s son, in the still shootout of Jan. 9, 1924. Baker put her under surveillance, with his deputies following her from Upthegrove Beach at Lake Okeechobee to Salerno, where they learned she had recently made a large ammunition purchase.

POSSE ORGANIZED

Learning of the deputies’ presence in Salerno, Ashley and three confederates — thought to be Clarence Middleton, Joe Tracy and Ray Lynn — escaped to the woods to the west and abandoned their boat. The next day, Sept. 30, Baker gathered a posse of 50 men, organizing them in squads and placing them at points where the gang might search for food and supplies. Some of the searchers included deputies from Osceola County who were seeking gang member Joe Tracy, who was a suspect in the Sept. 9, 1924, murder of C.O. Delesdernier.

As the sheriff went to a railway station to wire for reinforcements, it was reported that George Mario, John Ashley’s brother-in-law, was seen driving a vehicle with Joe Tracy inside and was heading west. 

With the gang hiding out about a mile and a half west of Salerno, Tracy had been directed by John to head back to Salerno for food. But on his way, Tracy came upon a posse. When he attempted to turn back the posse cut him off.  He took off, boarding a train for freedom and separating from the other three, apparently for good.

Suspecting John, Middleton and Lynn were hiding out near Lugenia Ashley’s rebuilt home in Fruita, Baker posted a four-member posse in hiding 150 yards west of Lugenia’s home.  

GIVING A SIGNAL

Lugenia knew law officers were monitoring her, so when her son, John, and the two other gang members emerged from the woods about 1:30 p.m. to approach the house she stood on a stump, waved a handkerchief and let out a blood-curdling yell, recalled Stuart police Chief O.B. Padgett in Alice Luckhardt’s book, Florida Son. Then they scattered back into the woods. Some took cover behind pine trees, and both sides began firing and exchanged shots for about five minutes.

One of the deputies from the posse attempted to spray gang members with a machine gun with no luck. “The gun failed,’’ said an account in the Miami Tribune. “Its trigger was hung and Ashley and his followers sought refuge in the swamp land.”

After a period of silence, the law officers crawled to the gang members’ position, only to discover that they had already fled. Recovered nearby were a .38 automatic revolver thought to have been shot out of one of the fugitive’s hands and a large supply of ammunition.

FLIGHT TO THE EVERGLADES

The gang members then began an eight-mile trek west of Stuart through piney woods and palmetto and then sawgrass until reaching the safety of the Everglades. There, on Oct. 1, they robbed the camp larder of W.A. Roebuck. 

The next day they traveled 5 miles, reaching the St. Lucie Canal. To cross the canal, they had created a raft from a telephone pole and slats from an abandoned shack. They placed their supplies, ammunition and firearms on it, and then swam it to the canal’s north side, continuing to elude law officers.

The gang continued west 15 miles toward Indiantown, where Baker placed a guard in a low swampy area he anticipated the gang crossing. Once again, deputies and the gang exchanged shots, with two deputies slightly injured from flesh wounds.

Near a farmhouse, another detachment of deputies saw a man on top of a house who then got down and made a dash to flee with the others Inside the house, they found two young married couples told the deputies three men brandishing pistols and threatening their lives had come into the house. They said the three ordered the women to prepare them a chicken dinner. They said one of the men went up on the roof to serve as a lookout. As the food was being cooked, the lookout gave the alarm, and the three ran away.

The three found a high spot of dry land in the swamp where they camped overnight. Their distance had grown farther and Baker, convinced they were traveling to the state’s west coast, gave up the search.

Earlier in the week, on Oct. 3, three deputies searching mangroves behind Gomez found a hideout, framed in wood and covered in tarpaper and glass, believed to be the gang’s main ammunition dump. An automobile parked nearby also held ammunition. Deputies set fire to the camp and then stood back and “listened to the roaring of hundreds of shells as they exploded,” the Palm Beach Post reported.

BILL ARRESTED

The manhunt for John in early October didn’t deter the moonshining activities of his big brother, Bill, who was arrested Oct. 11 in Riviera on a firearms and moonshine charges.

The gun in question, which had been purchased just a few minutes before his arrest, was a new repeating rifle. Though the gun charge was dropped, Bill was sentenced to 30 days in jail on Oct. 16.  

A jury also found him guilty of driving an automobile while under the influence of liquor, but the 30-day sentence in that charge was withheld as long as he paid a $250 fine and his court costs.