12/16/1937 - After months of planning and labor, the day finally arrives in which convict buddies Ralph Roe (prisoner AZ-260) and Theodore Cole (prisoner AZ-258) decide to become the first men to test the vulnerability of their supposed escape proof home ... challenging the bars, walls, and water of the Federal penitentiary located on Alcatraz Island.
Theodore Cole is a twenty-five-year-old felon from Oklahoma with burglary, armed robbery, kidnapping, murder and two escape incidents on a record that began when he was fourteen ... he is serving a 50-year sentence. Ralph Roe is a thirty-two-year-old criminal also from Oklahoma with a resume that includes grand larceny, theft, harboring a fugitive, auto theft, armed robbery, burglary, and kidnapping ... he is serving a 99-year sentence. Both men are extremely bad apples!
Serving out their terms quietly, both with jobs in the prison's Model Shop, Cole with a position as a janitor and Roe with work converting used tires into rubber floor mats, sometime in 1936 the men discover a flaw in their confinement ... the bars in the windows where they work are not made of tool-proof steel and can be parted. Creating a make-shift saw, the men soon beginning carving away at a special window they have selected for their escape every moment they are not under observation by a guard, covering up their work from discovery with a camouflage mixture of paint chips and putty. Bars finally cut, the men then wait for an essential element of their plan that they know will arrive sooner or later ... the dense fog San Francisco is notorious for having and in December of 1937, the thick grey cloak they need to leave the island arrives.
Alcatraz Model Shop
A deterrent to escapes, a count of the men working in the Model Shop is made every thirty minutes, and when Officer Joseph Steele makes his rounds at 1:00 in the afternoon, all prisoners are accounted for. As soon as the officers leaves however, Roe and Cole make their move for freedom ... the cut bars are dislodged, the men climb through a 8 and 3/4 by 8 and 3/4 inches hole, drop five feet to the ground, use a twenty-four-inch Stillson wrench to twist off a padlock on a gate leading through a fence topped by five feet of barbed wire, drop twelve feet from a cliff on to a beach covered in car tires discarded by the Mat Shop, and then vanish into the waters of San Francisco Bay, never to be seen again, both drowning victims of a 7-9 knot ebb tide that is thought to have carried the men out into the Pacific ... at least that is the official story.
Cole rap sheet
Roe rap sheet
Missed when the count is next taken at 1:30, a massive search of both the island, the waters ringing Alcatraz, and potential landing sights takes place ... and a $500 reward for information leading to the arrest of the men is offered. Nothing comes of any of it though and when an inmate testifies that he had seen the men floundering in the water, Alcatraz officials and FBI personnel determine the men are dead. But are they? The active investigation of the missing men is not discontinued until September of 1974, and over the years there will be reported sightings of the escapees in a North Bergen, New Jersey bar, by a cab driver in Seminole, Oklahoma who claims he gave the outlaws a ride, by a bartender in Petaluma, by two hitchhikers in Tulsa who will identify the men from photos they are shown by police, Warden Johnston will receive a postcard from Colorado signed T. Cole, an inmate will receive a letter with the code the convicts had agreed to send if they successfully escaped that posits "business is good," and in 1941, the San Francisco Chronicle will run a story stating that the men are living in South America. Did they drown or make it to shore? To this day no one can say with 100% certainty what happened to Cole and Roe ... and the ghosts of the island aren't talking!