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Letters From Alcatraz - Michael Esslinger [120]

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LEGEND SHATTERED,” as the name “Alcatraz” had until then been synonymous with the word “escape-proof.” Fellow inmates Theodore Cole and Ralph Roe had been long-term associates at McAlester and Leavenworth prisons, both had established escape records, and each was known in their own right as a Houdini of escape. Their crafty escape plan would give them the opportunity to sneak beyond the view of a correctional officer, and then slip past the barbwire fences and into the chilly waters of the fog-laden bay, never to be seen again.

Theodore Cole


Theodore Cole

Theodore Cole was a violent killer who had escaped a death sentence through “sentimental pressure.” Born April 6, 1912 in Pittsburg, Kansas, Cole began his life of violent crime in his early teens. He was the youngest in a family of one brother and two sisters and grew up primarily in Tulsa, Oklahoma. His father died when he was only two years of age and his mother eventually remarried in July of 1925. It is documented that his mother and his new stepfather were both strict disciplinarians. His family moved about frequently as his stepfather, a paving contractor, strived to maintain steady employment.

In February of 1927, at only fourteen years of age, Cole robbed a gas station using a handgun. Cole’s criminal record would grow over the coming years to include a variety of burglaries, one of which would involve the non-fatal shooting of a police officer in Hot Springs, Arkansas. At seventeen, Cole robbed the Dr. Pepper Bottling Works in Tulsa, and this crime resulted in another conviction for armed robbery. His parents spent everything they had to defend their son, but their efforts ultimately proved unsuccessful. Cole was prone to intensely violent and unpredictable outbursts and District Judge Saul Yager sentenced him to die in the electric chair stating, “The boy is a potential killer and deserves such a sentence.” Cole had been sentenced to death without having committed murder and this initiated nationwide sentimental protests led by various women groups and civil rights organizations. The groups were successful in getting his sentence reduced from life to fifteen years, but it was a barren victory.

In November of 1933, while imprisoned at McAlester Penitentiary in Oklahoma, Cole attempted to escape and was critically wounded but survived and it only emboldened his violent tendencies. Only a few months after his failed attempt, Cole murdered his cellmate William Pritchard, using a homemade knife to stab him twenty-seven times. Amazingly, Cole was able to convince the jury that Pritchard had attempted to kill him, and therefore that he had acted in self-defense. On November 30, 1934 Cole managed to escape the Oklahoma prison by concealing himself in a laundry bag which was loaded onto a truck and driven into town. On the afternoon of December 5th, Cole secured a pistol and approached a forty-eight year old gentleman named James A. Rutherford, pleading that he was stranded and needed a ride into the next town. Rutherford obliged, and as they drove away, Cole drew his pistol and took him hostage. He forced Rutherford to drive him to Illinois, where he released him. Cole then stole another vehicle and traveled south, committing a few small robberies along the way for quick cash. Finally, on January 6, 1935 in Dallas, Texas, Cole was captured and extradited back to Oklahoma. This time the court showed less leniency, stating “He is moronic, vicious, and a killer” – and Cole was sentenced to fifty-years in prison.

Throughout his trial, Cole continued his efforts to escape from the Oklahoma County Jail, where he was incarcerated during the proceedings. He succeeded in sawing through several bars of his cell using a razor, and he continually boasted that he would eventually break out. He was considered such a high escape risk that a sensitive ribbon microphone was installed to monitor any unusual sounds emerging from his cell. On May 20 1935, Cole was transferred to Leavenworth Penitentiary in Kansas, where he renewed a longstanding friendship with Ralph Roe,

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