by Willie Drye
“John Ashley, one of the two members of the notorious Ashley gang still at large, today apparently had made good his escape as small searching parties, one by one, gave up the pursuit and returned to their homes,” said the Kansas City Star.
The gang had been dealt a stunning blow, but John Ashley wasn’t through yet.
A few weeks after the battle in the Everglades, publisher William Randolph Hearst and columnist Arthur Brisbane paid a visit to William Jennings Bryan in his Miami home.
Hearst, whose newspaper circulation war in New York with publisher Joseph Pulitzer is considered a major factor in pushing the United States into war with Spain in 1898, was at the pinnacle of his publishing influence. He owned twenty-eight newspapers in 1924, as well as news services, magazines, a film company, and real estate.
But Brisbane, who had been working for Hearst since 1897, was said to be the real brains behind Hearst’s success. And his boss had rewarded him. Brisbane was known as the highest-paid journalist in the United States, and he was fond of introducing himself by telling people how much Hearst paid him.
In his nationally syndicated “Today” column, Brisbane praised the “old-fashioned” beauty of Bryan’s home overlooking Biscayne Bay.
“This place of mine is the most beautiful spot in Florida, and, therefore, in the world,” Bryan told Brisbane.
But, Brisbane wrote, politics were “boiling and raging like lava” in Bryan’s heart.
Bryan was indeed trying to insert himself once again into national politics. He’d seriously considered running for one of Florida’s seats in the US Senate, and now was seeking to become part of the state’s delegation to the upcoming Democratic National Convention in June.
Not all of Brisbane’s travels in Florida made it into his column, however. Author Oliver Carlson wrote that railroad executives and real estate brokers wanted very much for Brisbane to see the beauty and the economic opportunities in Florida.
They knew that Brisbane was almost compulsive about real estate.
“Brisbane’s enthusiasm for real estate knew no bounds,” Carlson wrote. “He wrote about it in his columns. He spoke of it in his lectures. Friends, acquaintances, even strangers were urged to buy! Buy! Buy!”
Miami was in the early stages of the real estate speculation that would soon become a national mania. Solomon Davies Warfield, owner of the Seaboard Air Line Railroad, was smart enough to get Brisbane out of Miami and show him property where prices were not yet escalating. For two days, Warfield and Brisbane looked at property, including land in northern Palm Beach County near Stuart, on the St. Lucie Canal that connected Lake Okeechobee and the Atlantic Ocean.
There’s no record of whether Warfield disclosed to Brisbane the fact that he was making some big plans for that area. But Warfield’s plans certainly would have made the property more attractive to Brisbane, and Warfield and others who were deeply invested in southern Florida’s economic growth wanted very much for Brisbane to start mentioning Florida favorably in his columns, which were read by at least twenty million people.
The best way to get Brisbane to start endorsing Florida was to sell him some property. Brisbane was very interested—and he was not alone. Many others were also becoming quite captivated.
Across the United States, readers of newspapers and large-circulation magazines were learning about the incredible profits being turned by ordinary people who had simply bought some land in Florida. In March, for example, readers of The New Republic read about a woman who had just sold her house in Miami for $100,000—more than $1.3 million in twenty-first-century dollars. She’d bought it for $18,000 in 1921. Another investor paid $2,500 for Florida property in 1921 and turned down an offer of $25,000.
In the past, the stream of traffic into Florida had ebbed with the traditional end of the season in April. But that didn’t happen in 1924. Newcomers continued to pour in. The Dixie Highway was becoming crowded. “They come in droves, flocks, herds,” The New Republic wrote.
And they were enchanted by what they found.
A visitor in March 1924 sent a postcard to friends back home on Washington Street in Ogdensburg, New York, describing the enchanting surroundings during one of the frequent concerts in Miami’s Royal Palm Park—where even the birds seemed to join in the fun.
“Afternoons and evenings, a mockingbird sits nearby on a tree and sings beautifully along with the band and keeping in perfect tune and time,” the visitor wrote.
But if the concert—and the harmonious mockingbird’s accompaniment—were free, not much else was.
“There’s plenty to do if one feels like spending money constantly,” the Ogdensburg visitor wrote. “But there is a limit.”
There was no limit on prices, however. Prices for everything—food, hotel rooms, gasoline—were steep, and getting steeper. And those who came to invest were in for a shock.
“Even swampland several miles west of Miami was selling for fantastic prices by 1924,” said Miami historian Paul George.
Real estate broker J. Newton Lummus Jr. said land sales in Miami were “on fire” in 1924, and they would stay that way throughout the year instead of slowing down, as they usually did, when the tourist season ended.
It was the year, in short, that Florida starting taking on the aspects of a “modern, latter-day gold rush,” George said.
As real estate prices escalated and word of fast fortunes spread, more and more people came to Florida seeking instant wealth. The gold rush mentality set in, and in such an environment, writer Gertrude Mathews Shelby would later note, thinking too much about real estate investments was a hindrance to making money.
“The people who have made real fortunes check their brains before leaving home,” a real estate broker told Shelby. “Buy anywhere. You can’t lose.”
Handford Mobley, the daring youngest member of the Ashley Gang, was not at the Everglades hideout on the morning of the deadly shoot-out with lawmen on January 9, 1924. Some accounts say he happened to be making a run to the Bahamas when the gunfight happened. By other accounts, he was in San Francisco, and immediately started back to Florida when he read about the bloody battle in a newspaper.
By late summer 1924, however, he was back in Palm Beach County, and he and the surviving gang members were plotting another bank robbery.
On the afternoon of Friday, September 12, Mobley, John Ashley, and two occasional gang members, Joe Tracy and Ray Lynn, hijacked a motorist near Lantana, just south of West Palm Beach, and ordered him to drive south to Pompano, about halfway between West Palm Beach and Miami.
When they neared their destination, they ordered the driver to stop and Ashley tied him to a tree.
For thirteen years, John Ashley had been playing a deadly game of hide-and-seek with the law-enforcing Baker family of Palm Beach County. He was furious that Baker’s posse had killed his father in the January gunfight. Before he left the driver, he gave him a bullet. Assuming that the man eventually would be talking to Palm Beach County Sheriff Robert Baker, Ashley told him to tell Baker that he had another bullet just like that one for him.
Ashley and the three other gang members drove the stolen car to the Bank of Pompano. They followed their usual plan of striking in mid-afternoon, when banks typically were less crowded.
Reports varied as to how much loot the gang got, but it was probably at least $8,000 or $9,000 in cash and about $18,000 in government bonds. Before they left, Ashley gave another bullet to a cashier and told him to keep it as a souvenir.
They drove north in the stolen car and then headed west. Lawmen found the car abandoned near the banks of the Hillsboro Canal, a drainage canal that sliced through the Everglades to Lake Okeechobee. Once again, the Glades had swallowed the Ashley Gang.
Robbing the bank at Pompano seemed to energize John Ashley and Hand-ford Mobley. It had been a decent haul, but they wanted a spectacular take.
Ashley and Mobley had made many trips to West End to haul booze back to Florida, and they knew a huge amount of
cash flowed into the liquor dealers there every day—so much money that hundreds of thousands of dollars were routinely hauled from West End to banks in Freeport and Nassau. West End was isolated from the rest of the islands. A boat fleeing West End with, say, a huge amount of money could be in trackless open water in minutes.
Mobley, Ashley, and other gang members decided that instead of holding up bootleggers on the high seas, they would aim for a fatter target. They would raid the liquor dealers at West End.
Their plan worked almost to perfection. They raided several liquor warehouses and made off with around $8,000 in cash and a boatload of booze. The only flaw in their raid was that shortly before the Ashleys arrived, a government boat had left the harbor with $250,000 in cash.
After more than a decade of chasing John Ashley through the Everglades, it was becoming clear to police that he was practically invincible in his wilderness hideout. Soon, however, a powerful natural force would drive Ashley and his gang out of the Glades, and the cops would take full advantage of that vulnerability.
On October 14, a tropical storm formed in the western Caribbean Sea and quickly morphed into an extremely powerful hurricane. On October 19, the hurricane crossed the western tip of Cuba with winds that may have reached up to 165 miles per hour.
As the storm turned to the northeast and headed toward Florida, it weakened rapidly. By the time it came ashore on the Gulf Coast, it was only a minimal hurricane. Still, it dumped almost a foot of rain as it crossed the Everglades on October 21 and went back to sea.
The drenching downpour made life miserable in the Everglades for John Ashley, Handford Mobley, and other gang members still on the lam from the recent bank robbery in Pompano. Ashley, Mobley, and two other gang members decided they’d had enough of the soggy Glades for a while. They were going north to Jacksonville, planning to perhaps knock off a bank or two along the way. They would lay low in Jacksonville until they figured out their next move.
Their plans didn’t include Laura Upthegrove, and she wasn’t happy about being left behind. Soon after the hurricane had crossed Florida, Palm Beach County Sheriff Robert Baker learned that Ashley, Mobley, and gang members Ray Lynn and Clarence Middleton would be leaving for Jacksonville on Saturday, November 1. They would be traveling in a Ford.
Baker saw an opportunity to catch Ashley and his remaining gang members away from their protective Everglades, but he knew his movements were constantly being watched, and that if he headed north around the same time as Ashley, his quarry likely would be warned.
Baker was running for reelection on Tuesday, November 4. While he announced that he would be campaigning in Palm Beach County on November 1, he quietly sent four of his deputies north to Fort Pierce, where they reported to St. Lucie County Sheriff J. R. Merritt.
In 1924, there was only one road into Jacksonville from southern Florida, and that route would take Ashley across a wooden bridge over the Sebastian River, about fifteen miles north of Vero Beach. Merritt decided to set up a roadblock at the bridge and grab Ashley there.
Merritt and two of his deputies joined the four Palm Beach County lawmen. Around sundown, they drove north to the bridge.
Merritt left his deputies on the south bank of the Sebastian, drove his car across the bridge, concealed it, and then walked back across the bridge.
The lawmen hung a chain across the entrance to the bridge and attached a red lantern to the chain. They hid in bushes and underbrush beside the road and waited.
Shortly before eleven p.m. a car with two men stopped at the bridge entrance. Moments later the Ford with John Ashley and his gang rolled to a stop behind the first car.
“We waited until they stopped, then came up from behind and covered them with our guns,” Merritt later told the Evening Independent of St. Petersburg. “They were caught unawares, being interested in seeing why the car ahead had stopped.
“When we came up alongside, John Ashley saw me first and grabbed for his rifle. I pushed a shotgun in his face and Deputy Wiggins pushed a gun into his ribs at the same time, telling him to throw up his hands or we would blow his head off.”
The cops disarmed the four men and ordered them to get out of the car and stand in front of the headlights.
Merritt later told reporters that he’d ordered the other lawmen to carefully search the four fugitives while he crossed the bridge to get his car, where he’d left his handcuffs. That was a lie, although the truth about what actually happened that night would not be known for more than seventy years.
The lawmen handcuffed John Ashley, Handford Mobley, Ray Lynn, and Clarence Middleton. Their hands were cuffed in front, and they were ordered to raise their hands above their heads and to not move.
Merritt then asked the men who’d arrived at the bridge just ahead of the Ashley Gang to give him a ride across the bridge to get his car to take them back to Fort Pierce. When he got to his car, he sent the men on their way and started back across the bridge in his car.
The cops guarding the gang members were edgy. After the January shoot-out in which his father was killed, John Ashley had said that he would kill any lawman who confronted him.
The deputy guarding John Ashley warned him he’d be shot if he moved. Ashley stood motionless for a few moments, but then made that sudden movement he’d been warned against. He took a quick step forward and started to drop his manacled hands. Maybe he was making a move for a concealed weapon that the cops hadn’t found, or maybe the car’s headlights had attracted mosquitoes—always plentiful after a hurricane has dumped heavy rains—and he’d been bitten. Whatever the reason, the deputy guarding him fired, and fired again.
Hearing the shots, and perhaps thinking that Ashley was making a move for a gun—or perhaps just waiting for an excuse to shoot—the other lawmen gunned down the other three gang members.
When Sheriff Merritt returned, he and his deputies removed the cuffs, loaded the four corpses into the Ford, and hauled them to an undertaker in Fort Pierce.
But Merritt told the Evening Independent a different version of how the four fugitives had died. He said they had not yet been handcuffed.
“When I returned, I stopped my car with the lights shining on the party,” he said. “I got out and went to the side door of my car to get the handcuffs.”
Merritt said the four men had not been searched, and that Ashley “gave a signal and all of the outlaws grabbed for their six-shooters. Then the shooting began,” he said.
A few days later, Merritt told the same story to a hastily convened coroner’s jury, and the jury ruled that the shooting of the four gang members had been justified. As unlikely as it would seem that an experienced lawman would not have immediately searched four notoriously dangerous criminals for weapons, or that he would have left handcuffs that he knew he would need on the other side of a long bridge, no one, other than perhaps John Ashley’s grieving mother, wanted to punish the men who had finally rid South Florida of the Ashley Gang.
John Ashley, Handford Mobley, and Ray Lynn were buried near the Ashleys’ modest home on November 4, 1924. Miami Herald reporter George L. Bradley turned the funeral into a maudlin portrait of a mother’s grief.
After stifling her emotions while the coffins were carried to the open graves, Lugenia Ashley began sobbing, Bradley wrote.
“There they are—three of them,” she wailed. “They killed them for not a thing in the world.”
Turning her gaze to the grave of her husband who’d been killed in the January gun battle in the Everglades, she said, “He never wanted to harm a hair on anybody’s head.”
“It’s [Sheriff] Bob Baker’s work,” she concluded. “We never did anything to him. I hope he’s paralyzed tomorrow and they have to feed him out of a spoon for the rest of his life.”
Decades later, author Ada Coats Williams interviewed the deputy who’d killed John Ashley at the Sebastian River bridge on November 1, 1924. She never identified the deputy, but she later quoted him in her 1996 book, Florida’s Ashley Gang.
A part of the wild Florida frontier died the night that John Ashley and his gang members were gunned down on the banks of the Sebastian River. Their violent deaths, coming at the moment that a growing tide of fortune seekers was beginning to flood Florida, also marked the end of the first phase of the Florida land boom.
The people pouring into Florida would be just as eager as the Ashley Gang had been to grab all of the money they could and run; they would just use different methods to snatch their riches.
On the day after Ashley, Mobley, Lynn, and Middleton were killed, an advertisement for Coral Gables was published in the Atlanta Constitution.
“The tropical beauty which appears in such overflowing abundance is only one of the many attractive phases,” the advertising copy read. “Certainly no state in the Union holds such unlimited opportunity for profitable investment as Florida does today.”
Coral Gables developer George Merrick was an honest man trying to build something beautiful, but many of those who followed his lead had no such scruples. The new robbers coming into Florida didn’t need guns to get rich; all they had to do was play on the greed of other newcomers who wanted to make a quick fortune without having to think about it too much. They would be ripe for the picking.
CHAPTER FIVE
The Stars Shine Brightest in Florida
BY THE WINTER OF 1924–25, GILDA GRAY HAD COME A LONG, LONG WAY FROM the old neighborhood in the Milwaukee suburb of Cudahy, where she had been known as Marianna Michalska.
Gray came to the United States as a child with her family from what is now Poland in 1909. In January 1925, she was twenty-three years old and in her second marriage, having danced her way onto Broadway with the Ziegfeld Follies. Her sinuous dancing had even caught the attention of that darling of the Jazz Age, author F. Scott Fitzgerald, who mentioned her in a scene in his classic 1925 novel, The Great Gatsby.