Alcatraz spent 29 months holding some of the country's most notorious criminals, including Al Capone, George "Machine Gun" Kelly, and Robert Franklin Stroud. Despite being dubbed as inescapable, several prison escapes were made on the island. Over the years, 14 different escape attempts were made by 36 inmates. Of these, 23 were caught and captured, six were shot and killed, two drowned, and five were never found. Two of the men never found were Theodore Cole and Ralph Roe.

Cole & Roe

Theodore Cole and Ralph Roe were both convicted robbers in Oklahoma. However, after independent escape attempts from McAlester Prison, the pair was sent to Leavenworth Prison high security and then eventually Alcatraz in 1936.

The two got jobs working at the facility's mat shop, where old tires were cut up and made into rubber mats for the Navy.

During their time here, the two used a hacksaw blade to weaken the bars on the window. They disguised their work each day with a combination of grease and shoe polish.

The Escape

On December 16, 1937, a particularly foggy day, the prison guards made their routine inmate check at 1:00 pm. Cole and Roe were both present. However, when the call was made again at 1:30 pm, the pair were missing.  

Upon investigation, the guards found a hole in the mat shop window. Two bars and three heavy window panes were compromised and had a hole that was nearly 9 inches high and 18 inches long. Once outside of the shop, Cole and Roe used a wrench to open the gate lock and dropped 20 feet onto the beach.

What Happened To Roe & Cole?

Prison officials thoroughly checked the beach and land surrounding Alcatraz and concluded that they had died either from drowning or the unusually cold water.

Over the following days, weeks, months, and years, different sightings were reported. One came from two hitchhikers who claimed to run into the pair. Similarly, a San Francisco Chronicle in 1941 reported the pair were living in South America. A cab driver in Theodore Cole’s hometown also told police that he had been shot by two men that matched their warrant photos.

What really happened to the pair?

No one knows.