Theodore Cole

Theodore Cole (February 6, 1913 - c. December 16, 1937 or later) with Ralph Roe took part in the second documented escape attempt from Alcatraz, in 1937. Although officials were quick to conclude they perished in the attempt, their remains were never found, making the incident the first to shatter Alcatraz's reputation as an "escape-proof" prison.

Cole and Roe, both convicted bank robbers in Oklahoma, had been caught during earlier, independent escape attempts from that state's McAlester Prison. Judged to be escape risks, they were both incarcerated in high-security Leavenworth Prison, then transferred to higher-security Alcatraz in 1936. The two were given jobs working in the prison's Mat Shop, a facility at the northernmost point of the island, where discarded automobile tires were cut up and converted into rubber mats for the U.S. Navy.

On December 16th, 1937, a dense fog swept through the San Francisco Bay, impeding marine traffic and reducing visibility on Alcatraz. At 12:50 p.m., a routine headcount at the Mat Shop showed all prisoners accounted for. But at the next headcount, just forty minutes later, Cole and Roe were missing. On one window, the reinforced bars had been bent and the multiple panes of heavy-duty glass shattered, creating a hole eight and three-quarters inches high and 18 inches long.

Hampered by the thick fog, guards were able to turn up only one trace of the escapees: an abandoned wrench from the Mat Shop, which had been used to partially dismantle a gate on the outermost fence. An extensive, multi-day search ensued; portions of the island were flooded with tear gas in an attempt to flush out the escapees, with no result.

An investigation concluded that Cole and Roe had prepared for the escape well in advance, using a hacksaw blade to weaken the window bars and disguising the damage with a mixture of grease and shoe polish. After taking advantage of the fog, they entered the water, presumably relying on floats improvised from tires or fuel canisters. There was no evidence to suggest they had constructed or launched a raft.

Prison officials concluded that Cole and Roe's lives ended, by drowning, shortly after their escape. The swift ebb tides at the time, estimated at 7-9 knots, would have swept even an expert swimmer out of the bay and into the Pacific Ocean. The dense fog would have made it almost impossible for outside confederates to pick them up on a boat, nor could the swimmers know whether or not they were swimming toward shore.

However, police departments in the surrounding counties and the FBI followed up every tip and rumor, with no success. In the following days, months and years, there were various reports of sightings but their validity is unknown. Sightings included two hitch-hikers, who claimed they had seen Roe and Cole and identified them to police by their photos, a San Francisco Chronicle reporter in 1941 declared that the pair were living in South America and a cab driver in Cole's Oklahoma hometown who told police he had been shot by men he recognized as the two escapees.