Theodore Cole and Ralph Roe

Imprisonment

Cole and Roe, both convicted bank robbers (Cole went into Alcatraz for kidnapping also) 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. They 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.

Roe, an Oklahoma bank robber, was originally captured after a shootout with local police and FBI agents in Shawnee, Oklahoma on December 30, 1933. This same gun battle claimed the life of Roe's partner, Wilbur Underhill. Cole had been given a death sentence by means of an electric chair for his role in the robbery of a bottling works plant in Tulsa, Oklahoma.

Escape and disappearance

On December 16, 1937, a dense fog swept through the San Francisco Bay, impeding marine traffic and reducing visibility on Alcatraz Island. Cole and Roe were working in a tire repair shop. A routine headcount at 12:50 p.m. showed all prisoners accounted for. At the next count, at 1:30 p.m., the two men were gone. Two iron bars and three heavy glass panes of a window in the shop had a hole 8 ³⁄₄ inches (22 cm) high and 18 inches (46 cm) long. Once through the window, they slipped down to the gate of a high wire fence, concealed by the fog. With a wrench taken from the tire shop, they forced the gate lock and dropped twenty feet to a beach. Their trail vanished at that point.

An exhaustive search of the island revealed nothing; guards found only the abandoned wrench. 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. Subsequent investigation revealed 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. At the beach, the men presumably entered the water, 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 drowned 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 fog was so thick that it would have made it almost impossible for outside confederates to pick them up by boat, nor could the swimmers know whether or not they were swimming toward shore. It is most likely that Roe and Cole drowned, and that their bodies were swept out to sea with their flotation devices.

Despite their likely fate, police departments in the surrounding counties and the FBI followed up every tip and rumor. In the following days, months and years, there were various reports of sightings, but their validity is unknown. Two hitchhikers claimed to have seen Roe and Cole, and identified them to police by their photos. A 1941 San Francisco Chronicle report declared that the pair were living in South America, and a cab driver in Cole's hometown of Seminole, Oklahoma told police he had been shot by men he recognized as the two escapees.

The Seminole Producer reported on June 7, 1939:

Oklahoma officers seemed intentionally to try to not identify the escapees as they continued their hijacking spree in the Seminole, Tecumseh and Shawnee Oklahoma area. The Seminole Producer reported on June 24, 1939: