The Prison Guard

A young man’s primary goal in life was to become a security guard at the local prison. After getting out of high school, the first thing he did was go to the prison and ask for an application, but he was told they weren’t hiring. Disappointed, he signed up for a stint in the Army, but not one week later he found a want ad in the newspaper saying “LOCAL PRISON NEEDS GUARDS.” Unable to break his Army commitment, he uttered the now-famous line, “Damn, I could’a been a con tender!”


An alternative version follows.

Aicatraz Prison, often known as the “Rock,” is on a small island in San Francisco Bay.

Alcatraz has long been the most famous prison in America. It started as a military prison during the Civil War and became a federal prison in the early part of the twentieth century. When it closed in the 1960s, it had housed such famous con men as the Birdman of Alcatraz and Al Capone.

Within the world of federal penitentiaries, Alcatraz attracted a lot of prospective guards to tend the prisoners. Sometimes two and three generations of the same family had members working as guards at the “Rock.”

In one local San Francisco family, working at Alcatraz spanned three generations, but unfortunately, not a fourth. One young man was not destined it seemed to follow in his father’s, grandfather’s, and great-grandfather’s footsteps. As is common with the new generation, this young man preferred a more professional calling, and he graduated from law school, became a district attorney, and finally built a successful private practice.

He was asked several times to become an officer at Alcatraz, and he was even asked to consider becoming the warden. Yet his private practice consumed too much of his time.

After several government inquiries, he always demurred, always refusing the honor of heading the prison.

Finally, in 1963, he decided to retire from law having built a secure nest egg, and he himself asked if the warden’s job was still available. Unfortunately, the Justice Department had decided to close Alcatraz, and when the federal officials told him that no there would be no job at Alcatraz for him, he could only reply, “I coulda been a con tender.”

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