At about 9 a.m. on Sunday, June 12, 1938, Galveston County Jail guard E.E. Goode climbed the stairs to the fourth floor “Iron House,” home to the jail’s federal prisoners. He unlocked the outer door and called out to Raymond Tyler, a 27-year-old serving four years for theft and burglary. His mother had come to bring him some tobacco.

When Goode swung open the door to Tyler’s cell, the inmate pulled a gun and leveled it at his head.

“Don’t kill me,” Goode reportedly begged, according to reports in the Galveston Daily News. “I’ll do anything you say.”

Tyler ordered the jailer to release two more prisoners: Pete Calandra, 32, serving a 12-year sentence; and Ed Sutton, 34, serving an eight-year sentence. Like Tyler, both men had been convicted for theft and burglary.

The three prisoners ordered Goode to lock himself in “the tank” with the other prisoners, but the guard hesitated. When Tyler started to push him into the cell, Goode swung his bunch of keys toward the gun, according to the other prisoners who watched the escape unfold. Tyler fired twice, striking Goode once in the chest.

As the guard crumpled to the floor, the prisoners raced down stairs to the first floor, where head jailer William Lindgren was coming out of his office. They yelled for him to open the outer door. He tried to barricade himself in a closet but they caught him, knocking him to the ground. Using two metal bars taken from his cell, Calandra gave Lindgren a savage beating. When he finally dropped the keys, the men grabbed them and ran. They barely had time to notice the wharf policeman standing at the bottom of the jailhouse steps as they careened down the street.

In front of A. Longo’s grocery store at 1601 Ave. A, they spotted a black sedan—with the keys inside. They piled in and sped toward the West End.

Despite having several skull fractures, Lindgren managed to radio for help. Fifteen minutes later, the entire Galveston police force and half the Galveston County Sheriff’s Department had gathered at the jail. Officers rushed Goode to the hospital but he died before he got there. Sheriff Frank Biaggne, who tripped down his front steps and broke his ankle in his haste to get to the jail, ordered blockades at all roads leading off the island. Traffic on Broadway slowed to a “snail’s pace” as officers at the causeway checked every vehicle headed for the mainland. But the escapees were long gone.

While officers combed the island looking for them, Tyler, Calandra, and Sutton hunkered down in the brush at the edge of a pasture on the West End. At dusk, Tyler snuck back into town for some food and water. The men stayed hidden all day Monday and concocted a plan to sneak off the island undetected. Early Tuesday morning, they stole some food and a skiff from a West End fishing camp. Under cover of darkness, they made their way up the Intercoastal Canal. Once they reached the mainland, they stole a car parked near the water and looted clothes, food, water, and money from a house near the ship channel. They got about a mile down the road to Beaumont when the car stalled. Tyler announced a new plan: They would steal another car, rob a few banks, and head to East Texas to hide out. Sutton wanted no part of it. When he turned to walk away, Tyler raised his gun to shoot Sutton in the back. Calandra convinced him not to fire the shot, and Sutton disappeared into the woods.

Now on his own, Sutton hopped a train to Memphis and then on to Baltimore, Philadelphia, and Wilmington, Del., before returning to Philly. Calandra and Tyler went on to Oklahoma, Colorado, and Washington state.

While the men enjoyed their freedom, Biaggne and his deputies grew increasingly frustrated by the lack of clues in the case. They quickly realized the men had escaped their dragnet and alerted police departments in other states where the men had family connections. The FBI even joined the hunt, but the men remained at large. While police all across the country continued to look for the fugitives, Biaggne focused his attention on the gun and how Tyler smuggled it into the jail. The sheriff arrested Tyler’s mother but released her after a few days. The search for the gun smuggler turned out to be as frustrating as the hunt for the escapees.

But the men couldn’t stay hidden forever. Calandra’s time on the lam ended first, when police in Salt Lake City, Utah, found him on July 8, sleeping in a stolen car. After “long questioning” Calandra admitted to local officers that he was one of the Galveston escapees. He tried to fight his extradition to Texas, but Biaggne wasn’t about to let him off that easily. He traveled all the way to Utah and personally presented extradition papers to Gov. Henry Blood to secure Calandra’s return to the island.

Sutton got caught next, on Sept. 1 in Des Moines, Iowa, after breaking into several houses. He didn’t object to coming home and gave Biaggne plenty of details about the escape and the aftermath.

“I am glad to get home,” Sutton said between gulps of hot coffee (in a post-capture interview with Biaggne observed by a reporter from the Galveston Tribune). “When they arrested me, I told them what I had done and that I wanted to get back home.” He especially looked forward to being reunited with his life story and “observations,” which he’d written down during his last stay in the Galveston County Jail. He told the Tribune he hoped the guards hadn’t lost it.

Tyler managed to avoid capture the longest, until Oct. 16. Acting on a tip from Calandra and another former jail inmate, Biaggne had warned police in Tacoma, Wash., to be on the lookout for the fugitive. An officer eventually discovered him on the side of the road, working on a car.

“I just stole this car in Seattle, and here it is stalled,” Tyler reportedly told the officer when he approached.

“Well, in that case, you’re under arrest,” the surprised officer said.

Tyler made a full confession, admitting he was the “trigger man” responsible for killing Goode. He didn’t bother trying to fight extradition to Texas, even though he must have known Galveston prosecutors would seek the death penalty.

All three men went on trial separately in November. Sutton got life in prison. Prosecutors asked for the death penalty for Calandra, alleging he was just as responsible for Goode’s death as Tyler.

“We don’t ask for any middle ground,” Assistant County Attorney Emmett F. Magee told the jury. “We ask you to put him in the electric chair or turn him loose!”

After deliberating for eight hours, jurors struck a compromise and gave him a 50-year prison term. Calandra “appeared elated when the verdict saved him from the electric chair,” according to the Tribune.

Tyler’s attorneys tried to argue their client couldn’t be held responsible for his actions because doctors who evaluated him determined he was “feeble-minded.” One psychiatrist testified that Tyler was “a chronic psychopath, maladjusted, easily influenced and below-normal mentally but not insane.” They blamed another inmate, George Newsom, for smuggling the gun into the jail and planning the escape. Newsom allegedly decided at the last minute not to leave after his lawyer told him he had a good chance of beating the charges against him at the time. Tyler took the stand in his own defense, insisting he never intended to shoot Goode. Prosecutors said his intent didn’t matter.

“Do your duty as red-blooded Americans, gentlemen,” County Attorney Charles Theobald told jurors. “And bring in a verdict that says a life for a life. … Do not mar the white flag of justice by dealing any differently with this defendant than he dealt with Ernest Goode.”

The jury deliberated for 24 hours and settled on a life sentence.

Neither Tyler nor Sutton learned their lesson. In 1943, both men escaped (separately) from the state prison in Huntsville. Police quickly recaptured them.

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