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Throughout his trial, Cole continued his efforts to escape from the Oklahoma County Jail, where he was incarcerated during the proceedings. He succeeded in sawing through several bars of his cell using a razor, and he continually boasted that he would eventually break out. He was considered such a high escape risk that a sensitive ribbon microphone was installed to monitor any unusual sounds emerging from his cell. On May 20 1935, Cole was transferred to Leavenworth Penitentiary in Kansas, where he renewed a longstanding friendship with Ralph Roe, a fellow inmate he had known at McAlester.

Ralph Roe

Ralph Roe

Ralph Roe was born on February 5, 1906 in Excelsior Springs, Missouri, and like Theodore Cole, he had endured a troubled childhood. Roe’s mother died of tuberculosis when he was only nine, and he later lost his two sisters to the same disease. At fourteen, Roe quit school and ran away to California. It was in Los Angeles that Roe was convicted of his first robbery in April of 1923, and this would be only the beginning of his lengthy criminal record. In July he was sent to the Preston Reformatory in Ione, California, but he escaped and trekked onward to Little Arkansas. Roe would then go on to commit a string of robberies throughout the west. His robberies became ever more violent, and one resulted in a gun battle which left accomplice Wilbur Underhill wounded and bleeding to death, hiding in the back of a furniture store.

Then on September 10, 1934 Roe and his accomplice Jack Lloyd robbed and took hostages at the Farmers National Bank in Sulphur, Oklahoma. This Federal crime would earn him a ninety-nine-year sentence and a recommendation for transfer to Alcatraz. Like Cole, Roe had also previously attempted to escape from McAlester. He had gotten another inmate to nail him into a utility crate, but he quickly started to suffocate inside of it, and thus was forced to abandon his plan. Both Cole and Roe were transferred via the same train from Leavenworth to the Rock.

Ralph Roe’s conduct report at Alcatraz.

Alcatraz

The two inmates maintained a close friendship at Alcatraz, both taking paying jobs and working side-by-side in the Mat Shop. The Mat Shop was a facility where prison workers transformed used car tires into rubber mats for the Navy, and it was located on the bottom floor of the Model Shop Building at the northernmost tip of the island. The area was recognizable by the piles of discarded tires that were pitched down from the industry building, littering the waterline.

Roe and Cole had spent several weeks in preparation for their escape, studying the habits of the correctional staff, and working to identify potential loopholes in the security system. Using a stolen hacksaw blade, they were able to saw their way through the steel sash window grill, packing the saw gaps with grease and shoe polish to avoid detection. On the morning of Thursday, December 16, 1937, dense fog forced the docking of almost all the small vessels in the area. The forceful currents leading out past the Golden Gate Bridge and toward the Pacific Ocean were fluctuating between seven to nine knots, creating what were considered death-trap conditions for anyone willing to try their fate in the perilous waters. The two inmates were likely not aware of how dangerous the currents and foggy conditions could prove to be. It was speculated that they might have seen the spell of bad weather as an opportunity to escape under cover of dense fog.

At about 12:50 p.m., the inmates returned to the Industries Building from the mess hall after lunch, and underwent a count by Junior Officer Joe Steere, who found all inmates present and accounted for. Steere was alternating his patrol between the Blacksmith and Mat Shops, and he left the Mat area unattended while performing his routine watch. Steere returned to the Mat Shop for the 1:30 p.m. count, but inmates Cole and Roe were not at their assigned work detail.