You may have heard that Alcatraz, the infamous federal prison on a forbidding island in San Francisco Bay during the mid-20th century, was a place from which no one successfully escaped. You might also have heard that that claim is equivocal; three convicts, Frank Morris and the Anglin brothers, may have successfully escaped in 1962, in an incident chronicled in the surprisingly accurate 1979 Clint Eastwood film Escape from Alcatraz. But unless you’re a buff of Rock history, chances are you probably haven’t heard of Theodore Cole and Ralph Roe. They may–heavily emphasize the may–have escaped from the island 77 years ago today, on December 16, 1937. But, as with much other Alcatraz lore, it’s impossible to tell for sure.

Alcatraz is a strange place with a very dark and troubled history. The chapter of that history that made it most famous began in the early 1930s, when the feds decided they needed an ultra-secure facility to house the super-criminals, many of them emerging from the lawless Prohibition era, that kept escaping from other prisons. Gangster Al Capone was shortly jailed here, and Alvin Karpis, FBI’s Public Enemy #1 in 1935, spent many long years locked up behind Alcatraz’s thick walls and bars. In fact, the story of Cole and Roe has a lot to do with Karpis–and he may be the reason why we don’t know more about it.

Theodore Cole was a bank robber from Oklahoma. In December 1933 FBI G-men caught up with him in a shootout in Shawnee, Oklahoma, and, after killing his partner, managed to take him alive. Roe was also from Oklahoma, and had been sentenced to death after knocking over a factory in Tulsa. Both went to the Rock. They wound up working together in the prison shop, repairing tires. There the two of them hatched an escape plan.


Alvin Karpis, a notorious Depression-era bank robber, served longer at Alcatraz–26 years–than any other person. He was paroled in 1969 and died in Spain a decade later.

It took a while for their plan to come to fruition. Using hacksaws, Cole and Roe made and enlarged a small hole in the barred windows of the tire shop. At night they disguised the damage by filling in the bars with goop made from shoe polish and grease. They watched the skies for the signal for their escape: a heavy storm with thick fog. On December 16, 1937, a very foggy day even by San Francisco standards, they judged the time was right. Sometime between 12:50 PM and 1:30 PM, when guards conducted head counts, Cole and Roe wiggled through the 18-inch-wide, 8-inch-tall hole they’d made and ran toward a fence, thinking they were obscured by the heavy fog.

They then used a wrench to force open the gate in the wire fence. Jumping 20 feet down to the beach, it is believed they used some sort of floats–possibly tires taken from the shop–to try to brave the current and swim for nearby land. As their trail vanished from the beach and their bodies were never found, the FBI concluded that they drowned quickly once they were in the water.

This is not an unreasonable conclusion. San Francisco Bay is one of the most treacherous bodies of water in the world. Filled with brutal currents, hungry sharks and usually numbingly cold, especially in December, it’s doubtful even an Olympic athlete in perfect shape could survive a dip of more than a few minutes. Furthermore, Alvin Karpis, who told authorities he witnessed the escape, saw them go into the water and claims they were sucked under the surface by the powerful currents. Supposedly this convinced Karpis that escaping Alcatraz by water was impossible. He would remain incarcerated there until the prison closed in 1962; after he was moved to another prison he had the dubious distinction of teaching future mass killer Charles Manson how to play guitar.

Although it takes some liberties with the truth, the 1979 film Escape from Alcatraz, dramatizing the only (supposedly) successful escape from the Rock, is pretty accurate, and also a surprisingly good movie.

I have my doubts. Not about whether Cole and Roe made it–it seems almost certain they drowned–but about Karpis’s story. If the bank robbers waited until a storm with thick fog to make their escape, and Karpis was obviously inside the prison looking through the windows, how could he have seen them through the storm? Karpis was notoriously unreliable and no stranger to stretching the truth. I’m doubtful he saw anything, which means all the evidence we have about Cole and Roe’s escape comes from the hole in the window, the broken gate and the wrench they used to break it, which authorities found nearby.

As with all famous escaped criminals, many people insisted they saw Cole and Roe in following years. In 1939 they were supposedly seen committing more crimes in Oklahoma, and two years later there were reported sightings in South America. None of them were reliable. I think the Herculean undertaking it would have been to swim to safety across the bay in December, and then make a successful escape once back on dry land, was too much for these two-bit bank robbers.

Alcatraz was not escape-proof. In 2003 for the MythBusters show Adam Savage and Jamie Hyneman reenacted the famous 1962 escape–where the prisoners built a makeshift raft–and proved that it could be done. But that was many years later, and the “learning curve” needed for a successful escape from the prison was extremely steep. Cole and Roe almost certainly didn’t make it, but they remain part of the Rock’s bloody, daring and unsettling history.