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Coy feverishly attempted to find work, in hopes of making a decent life for himself and his wife. He was a gifted craftsman and artist, and made use of his talents as a decorator and painter. However, despite his earnest attempts, the Great Depression had left him unemployed and desperate to support himself. Bernie found himself backed into a corner with few options left by which to survive. In 1923 Coy was arrested in Draper, Wisconsin, for violating liquor laws along with an assault and battery charge. He was released with time served and fined $250, which he clearly could not afford to pay in his state of unemployment. He was convicted of larceny charges in 1928 and 1930, and eventually served nearly five years in the Wisconsin State Penitentiary.

Reading Coy’s letters from the years prior to his Alcatraz escape attempt, it would be nearly impossible to predict his violent and premeditated break for freedom. His letters articulate what appear to be a true desire to reform, as is illustrated in these excerpts written to the superintendent of the prison where he was incarcerated on August 30, 1936:

I regret that this request [for release consideration] must be made under the present unfavorable conditions, rather than under circumstances relevant to the continued progress of some noble social service. Please believe me sincere in my regret, and if there is a loyalty of promise incapable of future betrayal, you may be assured, Sir, that your confidence in me, however great or small, shall never be abused. Since my incarceration, I have made a record which is the envy of everyone. Not one time have I been disobedient, or sullen, nor have I set an example which would not be commendable in the best society. I am a firm believer in discipline, and regulate my actions according to my belief. I believe I have proved myself trustworthy. I am president of the Holy Names Society here inside the prison, a Catholic society, and I know that I have acquitted my office satisfactorily every moment. I do know right from wrong, and certainly try to be well thought of by everyone I meet. The Army and the World War, at age seventeen, gave me a background upon which to build a life equally as remarkable as your own; and I may yet put the right foot first. I am not too proud to ask for help, nor too weak to win if refused. I am not guilty of any crime and have nothing of which to be ashamed. Your will is my determination, Sir, in prison or, at home. More than this no man can promise.

Only six months after composing this letter Coy was released from prison, but he was soon involved in another crime. On April 18, 1937, armed with a sawed-off shotgun, Coy robbed the National Bank of New Haven Kentucky with a friend named Delbert Lee Stiles, and a relative named Richard Coy. The three fugitives made off with just over two thousand dollars and retreated into a small cave by the Rolling Fork River. Three days after the heist, local farmers noticed smoke from their campfire and alerted officials. During the trial that followed, Coy was identified by cashier A.E. Kirkpatrick as the man who had walked up to the cage, drawn a sawed-off shotgun and held him at bay while an accomplice scooped up the money. On June 3, 1937, Bernard Paul Coy was sentenced to twenty-five years and five days in a federal penitentiary. The trio would all be sent to serve out their respective sentences at the Federal Penitentiary in Atlanta.

Bernie did not adjust well to prison life and frequently found himself in isolation as punishment for engaging in altercations with other inmates. It is recorded that Coy physically attacked another inmate with a brutal implement consisting of a razor blade mounted onto a toothbrush handle and this incident would earn him his one-way ticket to Alcatraz. Bernie arrived at Alcatraz on July 31, 1937, and he got off to a rough start during his first years on the Rock. On September 21, 1937 he participated in a work strike stating: “I’m not a big shot or looking for