On December 16, 1937, one of the densest fogs to ever occur in San Francisco blanketed the Bay Area, bringing visibility to near zero. That was just the break Alcatraz Prison inmates and convicted bank robbers Theodore Cole and Ralph Roe were waiting for to make their daring escape from what was known as “The Rock.”
The two were considered escape risks and were doing time for crimes in Oklahoma. They were moved from a prison in McAlester, Okla., to the maximum security facility in Leavenworth, Kan., then to Alcatraz in 1936.
Both had secured jobs in the prison’s Mat Shop, where automobile tires were shredded and made into mats for the Navy. On December 16, both were present for the 1 p.m. headcount, but the next count at 1:30 showed two prisoners missing. Cole and Roe had made their move.
The pair had previously sawed through iron bars with a hacksaw and covered their marks with a mixture of axle grease and shoe polish. Sliding through the bars and cutting a hole in the heavy glass window, the two convicts fled the shop with a stolen wrench, which they used to pry open a gate, all the time concealed by the dense fog. Once through the gate, they dropped roughly 20 feet into the icy waters of the bay. The men presumably entered the water and floated away on floats improvised from old tires and oil drums. Their trail vanished at that point.
An exhaustive search of the island turned up no evidence the pair had made it to the mainland. Prison officials presumed both Cole and Roe drowned attempting to reach the mainland.
Shortly after the escape, however, police departments recorded various reported sightings of the men. A crime spree in the Seminole, Okla., area in 1938 is reportedly linked to the two after a cab driver was shot while being hijacked for a bank robbery. Other sightings around Shawnee and Miami, Okla., were reported, but Cole and Roe continued to evade captors. As late as 1941, a San Francisco Chronicle article noted that the two were living well in South America, reportedly in Peru and Chile.
Cole and Roe’s departure from the island prison was only the second recorded escape from Alcatraz.