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Federal prison; Gardner’s name was synonymous with the island institution. He spent two years incarcerated on the island from 1934 until 1936 and after his ultimate release in 1938, he peddled a small informational book and narrated boat tours for San Francisco tourists. Jim Quillen once said that if the walls of Alcatraz could talk, every cell would be novel of tragedy and despair, and he felt that this was especially true in the case of Roy Gardner. When Gardner arrived on one of the first trains from Leavenworth to Alcatraz, he was already a “solid con,” or a seasoned inmate. Gardner was known to the public as a brilliant escape artist, and he was famous for his Houdini-like jailbreaks. Up until his arrival at Alcatraz in 1934, he had seemed nearly impossible to keep caged.

Gardner was born on January 5, 1886 to a poor family in Trenton, Missouri. He entered the U.S. Army, and served in the 22nd Infantry stationed in the Philippine Islands from 1903 to 1905. After returning to the U.S., he deserted the military because of what he described as “serious gambling debts.” Fearing for his life, he fled to Mexico and took a job working in the mines. In 1909 Gardner was arrested in Mexico for smuggling weaponry, and was sentenced to death by a firing squad for his involvement with the Mexican Revolutionary Army. While awaiting his execution, he was confined in a dungeon under the most horrific conditions. The cells were rat-infested and dimly lit, and he was forced to relieve himself in a bucket that was emptied infrequently. Just three days before his scheduled execution, he amazingly overpowered his sentry and fled to Arizona. From there he eventually traveled northwest to San Francisco.

On December 22, 1910, during the busy Christmas shopping season, Gardner robbed Glindemann’s Jewelry Store on Market Street in San Francisco. Posing as a distinguished customer, he waited as the clerk laid a full tray of diamond rings before him. After taking some time to examine the gems, he grabbed the entire tray and fled into the street, but he was quickly spotted and tackled by a San Francisco police officer. Following his trial he was sentenced to serve five years in a California state prison, and he entered San Quentin on February 16, 1911. He was by all accounts a model inmate, and worked productively in the Prison Industries. He was released in September of 1913, and secured a job at a copper mine in Kennett, California. He eventually took a welding job at the Mare Island Naval Ship Yard, and sold war bonds during World War I. During his short reprieve from crime, Gardner met and married a pretty waitress named Dolly Wades. But despite this interlude of normalcy, Gardner’s link to the world of crime had not yet dissolved.

Dolly Wades-Gardner

After a busted gambling spree during a business trip in April of 1920, Gardner was again arrested for robbing a postal mail messenger in San Diego, taking approximately $75,000 in bonds and securities. He was sentenced to a twenty-five-year Federal term at McNeil Island. The thought of enduring another prison term was unbearable to Gardner, and during his transfer by train, cuffed in hand and leg irons, he made a bold escape from the Federal marshals who were accompanying him. He somehow managed to secure their guns, and made them take off his shackles. He fled, and immediately thereafter committed another robbery. This time he had truly struck gold as his heist would net him over $200,000. But his luck was to prove short-lived. Only days after the robbery, Gardner was recognized while playing poker at a saloon in Roseville, California. The Porter House Saloon was only blocks from where he had committed the robbery. He was captured, and was sent back to McNeil to serve out an additional prison term. Amazingly enough, just like a modern-day Houdini, he again escaped from the Federal marshals. But he was recaptured soon after, and this time extensive precautions would be taken to ensure that he had no means of escape.

In September of 1921 Gardner was transferred to Leavenworth Federal Penitentiary,