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Authors: David Ward

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Alcatraz’s escape artists, however, confronted a custodial staff very intent on keeping them on the island. “The inmates’ job is to get out,” said a senior custodial officer; “our job is to keep them in.” With Alcatraz labeled by the press and the popular media as escape-proof—a characterization not seriously denied by the Bureau of Prisons or the Department of Justice—many guards and their supervisors took it as a personal and professional challenge to thwart escapes. In an ongoing battle of wits, skills, and courage, they took it on themselves to keep escape-inclined prisoners from locating, as one convict put it, “the hole in the Rock.”

Although many Alcatraz inmates were escape artists, planning a break was not for all prisoners. As in planning the robbery of a bank or monitoring the daily routine of a potential ransom kidnap prospect, plotting an escape required intelligence, skill, patience, and courage. Escape routes had to be carefully figured out, the patterns of guards monitored for long periods of time, the actions of escape partners closely coordinated, and clothing, ropes, flotation gear, and other paraphernalia constructed, prepared, and hidden. Such preparations occupied weeks and even months of time and involved activities that were risky in and of themselves. It is not surprising that most of the men who attempted to escape from Alcatraz had robbed banks or kidnapped someone, crimes involving considerable advance planning, a sense of timing, and the ability to think quickly and to act decisively while working under life-threatening circumstances—all the while maintaining emotional control, or what admiring confederates called “nerves.”

The custodial staff at Alcatraz expected that the greatest collection of escape artists ever assembled in one prison would devise some sophisticated escape plots, and they were not disappointed. Several of the attempts involved planning, preparation, and execution of such a high order that they rank at the top of the list of the most ingenious and daring escapes in American penal history. They have been featured in such films as
Escape from Alcatraz
and
Six Against the Rock
, and even today they are reenacted on various “true crime” television series.

Escape attempts from the island were concentrated during the period from 1937 to 1946. After 1946, only two serious efforts to break out occurred, both in 1962, and they contributed to the closing of the prison in March 1963. Several of the breaks that occurred during the prison’s thirty-year history came close to success—inmates were able to get out of their cells and the cell house or the industries building—but none of the escapees was able to overcome the last security barrier, the cold, fast currents of San Francisco Bay.

“LOST IN A FOG”

Theodore Cole, one of the first two men to test the Rock’s security system, had all the credentials that justified a transfer to Alcatraz. He was sent to the Oklahoma State Training School for Boys at the age of fourteen. Shortly after his release, he was convicted on a burglary charge and sent to the Arkansas State Penitentiary; a short time later he was released to Oklahoma authorities so that he could be tried for the armed robbery of a Dr. Pepper bottling plant in Tulsa. Armed robbery was then a capital offense in Oklahoma and the judge, contending that “the boy is a potential killer,” sentenced him, at age seventeen, to death in the electric chair. Subsequent protests by women’s clubs and other organizations, however, were successful in convincing the appellate court to set aside the death penalty in favor of a sentence of fifteen years.

At the Oklahoma State Penitentiary Cole got into a dispute with his cell mate, pulled out a prison-made knife, and stabbed the other man twenty-seven times, killing him. As this murder charge was pending, Cole escaped by concealing himself in a bag that was thrown in the back of a laundry truck. The truck drove out of the prison and Cole jumped off, unseen by the driver. While on escape status, he approached a man who was preparing to get into his automobile and drive to Cushing, Oklahoma. He asked for a ride and the driver agreed, but a short distance outside of town Cole produced a gun and forced the man to drive him to Springfield, Illinois. Cole was identified as the kidnapper by his victim, and because kidnapping had recently become a federal offense, state and local police were joined by the FBI in the effort to track him down.

On January 5, 1935, Cole was arrested in Dallas, Texas, and returned to Oklahoma City to be tried on federal kidnapping charges. In the Oklahoma City Jail he tried, unsuccessfully, to escape by concealing himself in a garbage can and by sawing the bars of his cell. On May 20, he pleaded
guilty to kidnapping in U.S. district court and was sentenced to a term of fifty years; Oklahoma authorities filed detainers to hold him after service of his federal sentence for his escape from the state penitentiary and the murder he committed there. Cole was shipped off to Leavenworth on the same day that he was sentenced. His admission summary classified him, at age twenty-three, as a habitual criminal; an FBI report characterized him as “moronic, vicious and a killer.” At Leavenworth Cole readily admitted to the staff that he had murdered his cell mate in the Oklahoma state prison and this statement, plus the length of his sentence and his record of escapes, provided the basis for the recommendation that he be transferred. Five months later he was on the Rock.

Ralph Roe was on the same train that brought Ted Cole to Alcatraz. Roe had also run away from home at the age of fourteen and had also compiled an impressive criminal record. After serving time in a youth prison in California for robbery, he traveled to Arkansas, where he was sent to prison on a grand larceny conviction; eighteen days after his release from Arkansas he was arrested for theft in Oklahoma and went off to the state reformatory at Granite City for two years; six months after his release from the reformatory he was sentenced to twelve years in the Oklahoma State Penitentiary for robbery with firearms. He served six years, but seven months after his release he was charged with harboring a fugitive and robbery with firearms, charges that were ultimately dropped; six months later he was arrested for auto theft and burglary. These charges were also dropped but two months later he was arrested for the robbery of the Farmer’s National Bank at Sulfur, Oklahoma, and for kidnapping the cashier as he and an accomplice made their getaway. These charges were not dropped. On January 18, 1935, he received a ninety-nine-year sentence and was transported to Leavenworth. The Leavenworth medical staff determined that he was “acclimating himself to his very restricted life in an unusually excellent manner; despite his 99 year sentence he is facing his fate in an optimistic manner and has retained a cheerful personality.” Despite this positive evaluation, he was put on the same train with his friend Ted Cole to help build the Alcatraz population.

Ralph Roe settled down to do his time quietly and soon won over the medical staff, who pronounced him “a likeable individual with good intelligence.” Ted Cole was caught up in several protests, including the strike that began a few months after his arrival. When asked by the deputy warden why he was refusing to work, Cole replied that he did not know what
the strike was about, but he “felt that he had to stick with the boys a few days as he had to live with them for many years.”
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Cole’s only other disciplinary reports were for possession of contraband (some clothes stolen from the laundry and a piece of fudge smuggled from the kitchen).

Cole and Roe, like so many of the escape plotters, understood that a man could not engineer a break if he was not as free as possible to move about the kitchen, the hospital, and the industrial area to look for weaknesses in windows, doors, and fences. The two created no trouble, attracted little attention from staff or inmates, and served their time quietly, but they were determined to find a flaw in the security system.

Their jobs in the Model Shop afforded them this opportunity. They discovered that the bars in the windows were not tool-proof steel, and that for relatively long periods between head counts they were not under direct surveillance by guards. Although a guard was stationed on the flat roof of the building, he could not be looking on every side of the building at once, and fog reduced his visibility.

Cole and Roe correctly saw that heavy fog would be the key to their escape because it would obscure their movements, both on the island and in the water. When the fog remained thick and close to the water on the afternoon of December 16, 1937, they were ready.

Inmates who worked in the industries shops were counted every thirty minutes and the two were observed at their jobs at 1:00
P.M
. by Officer Joseph Steere. After the count, Steere left the mat shop to check up on the inmates in other shops; when he returned to make the 1:30 count, Cole and Roe were gone. He called the deputy warden, heard the alarm siren go off, and began to look around the work area. He noticed that one of the windows was missing some bars. The officer assigned to routine patrol along the edge of the flat roof rushed to the bay side of the building but saw no sign of the men—even the fence gate through which they passed was closed in its normal position. He had not looked over the side of the building during the few minutes that the inmates were climbing out of the window, running to the fence, twisting off the padlock, and jumping down to the edge of the bay and swimming away from the island.

A massive search was launched, with Warden Johnston ordering several of his men to join San Francisco police officers in a search of every fishing boat that came in to dock at Fisherman’s Wharf and other piers. (As an indication of the poor weather that day, the guards reported that they helped search only fifteen boats, when normally fifty or more would have gone out and come back.) Angel Island, the closest landmass to Alcatraz,
was carefully searched, as was Red Rock Island, a rocky out-cropping located near Richmond some seven miles inland from the Golden Gate Bridge. No sign of the fugitives was found on these islands or along the shores of San Francisco, Sausalito, Tiburon, Richmond, Berkeley, Oakland, or other communities ringing the bay.

On Alcatraz, guards looked in every corner in the shop buildings, the docks, shrubbery, and sewers, and the caves along the shore at the northwest end of the island. The caves were searched with lights and the largest cave was flooded, first with tear gas and then with a gas that produced vomiting, and guards were assigned to watch the area around the entrances to the caves for any sign of life.

Prison officials hoped that the bay would offer up the bodies of the two convicts as tangible evidence that the escape attempt had failed. Harbor officials and keepers of the eight lighthouses then operating were contacted to inquire whether they had observed any unusual sights or events and urged to keep their eyes open for floating objects that might be related to the escape. The direction and rate of the flow of tides was calculated to plot the probable movements of bodies. Harbor officials reported that the afternoon ebb tide on December 16 was stronger than the returning flood tide, which meant that a body carried ten miles out with the ebb tide would return only six miles on the flood tide; bodies carried out under the Golden Gate Bridge, they said, would likely be returned to coastal shores rather than back into the bay.

Since Alcatraz represented the most visible symbol of the federal government’s promise to keep the country’s most desperate lawbreakers securely locked up, the disappearance of Cole and Roe tarnished the image of the escape-proof fortress that the Justice Department had sought to create. As the lead from the
San Francisco Examiner’
s full-page spread the next day put it,

Two desperate Alcatraz prisoners vanished from the American “Devil’s Island” yesterday into the obscurity of one of this winter’s heaviest fogs. Theodore Cole, 25, and Ralph Roe, 32, Oklahoma desperadoes with long careers of crime, apparently had escaped from the Federal Prison that was supposed to be escape proof.

The
Examiner
reported that the search for the two inmates was “one of the greatest manhunts in Northern California experience.” The paper offered a $500 reward for information leading to the arrest of the “desperadoes” and complained that when a boat hired by the newspaper approached Alcatraz, guards on the island fired warning shots across its
bow. The
Examiner
also ran a separate story in which the prison was labeled “a menace to San Francisco.”

When Attorney General Cummings and the Department of Justice decided to make Alcatraz an American Devil’s Island, vehement protest arose from San Francisco and all the Bay Region. The Bay Cities bitterly resented conversion of a beautiful island on San Francisco Bay into a sinister repository of what were advertised by the Department of Justice as the most vicious Federal prisoners in captivity. Repeated efforts were made to convince Cummings that Alcatraz was not escape proof. The
Examiner
had a girl swim completely around the island and back to shore as proof that escape by swimming was no very difficult matter. The fogs of the Bay as cover for an escape were no secret. But someone seems to have been too much intrigued by the publicity value of Alcatraz. Here was the most effective possible dramatization of the G-Man. All the nation’s Public Enemies on an island that loomed like a fortress under the windows of a million people. What a monument to the Department of Justice! Now the worst fears of this region may have been realized. If the two convicts that escaped yesterday have reached the mainland then two beasts have been turned loose upon these communities. If the men are as advertised, two of the nation’s most desperate criminals, they will kill any man, woman or child who stands in their way of escape. Their past records include kidnapping and murder. Their future records may well include another murder or murders. Even if they are later found hiding on the island or if they are drowned, the stupidity and cynicism that underlie the whole Devil’s Island scheme are apparent. Alcatraz was, and is, a bad choice, and it is a continual affront and menace to every city that borders on the Bay.
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