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The toughest part of Alcatraz was not the escape

by Frances Garcia
July 27, 2025

Alcatraz may be the most famous prison in the world. It is known for the infamous prisoners who spent time there, because it is said to be impossible to escape from, and because of its image as ‘The Rock’ both in pictures and in the famous movie of the same name. Yet if you talk to anyone who has served time at the prison none of these things stand out. The reason ‘The Rock’ is famous to prisoners is that it is the hardest time any prisoner has to serve.

Bryan Conway spent ten years in a prison in Atlanta and 20 months in prison in Alcatraz. He says the 20 months were far worse than the entire ten-year stint. To understand why you should really read Conway’s notes on his time there. His beautiful use of language paints an excellent picture of what daily life was like in this isolated forgotten place that was known by all. 

Conway describes the moment he arrived in Alcatraz as a good one. He had been transferred because he wouldn’t testify against an inmate in Atlanta who had stabbed somebody. When he reached his cell in Alcatraz, they already knew. The other inmates welcomed him because he had proven he wasn’t a switch and was someone that could be relied on. 

There were many famous inmates there during his time with the lead names of Capone and Machine Gun Kelly standing out. Conway didn’t spend any time with Capone but became good friends with Kelly while at the prison. On the outside, it is often believed that prisoners are judged by their crimes by other prisoners. That murderers are more revered than shoplifters. Conway says this is far from true. All prisoners are treated equally with the exception of those in prison for sex crimes. On the outside, we assume this is because even prisoners are disgusted by sex crimes but this is not true either. Conway says that those who commit sex crimes are simply not trusted. It is assumed that most are insane and can’t be relied on in a prison environment.

Conway says that the prisoners are not the problem in Alcatraz. In his time, there were 317 prisoners in Alcatraz, and 14 went terribly insane. Many more than that were what he describes as stir crazy. By this, he means they continue to function and complete the daily routines but they are walking around in a daze that they would never wake from. A concussion brought about by giving up on life. The hardest part of life on Alcatraz is the routine. In no other prison is the routine in place in such a strict manner. If you want to shave you have three minutes to complete it between 6 20 am and 6 25 am. There is no talking during meals and there is no chance to get away with any misbehavior. Prisoner counts are conducted every thirty minutes to ensure everyone is where they are supposed to be.

Even a good night’s sleep can not be counted on. The prison guards use this time for target practice and will shoot at targets outside to both intimidate and warn the cons attempting to rest inside.

While Alcatraz is often treated as this halloed place where men fear escape but the greatest convicts reside, what it is, is worse. It is a simple prison that is so strict and severe it kills every man inside by the method of routine. A routine that can never be escaped and captures every man’s sanity eventually. Conway’s reports are an incredible insight into the terrible time he spent there.

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