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The Story of the Mysterious Alcatraz Prison Break

By

Ami Ciccone

, updated on

February 27, 2020

Today, Alcatraz is one of the most visited places in the San Francisco area. It's a world-famous prison that only decades ago was the house of well-known federal prisoners. Escape from the island was believed to be impossible, and yet, over 30 prisoners tried to flee. While all of them are believed to have failed, three inmates escaped together.

One of them, John Anglin, allegedly reached out to the FBI in 2013 through a letter that might have shed light on the most mysterious escape in the history of the prison. But was it really him? Did they achieve the impossible?

A Barren Rock

Alcatraz was considered an ominous place ever since it was discovered by Spanish explorers. The rock has no flowing water. Therefore, there was no life in it—not even one single plant. Furthermore, its soil had nothing to offer to agricultural development.

Without beaches, boats had difficulty docking here, and there were only three places that were accessible to them. In short, it was the perfect place for a prison, which is what it eventually became. Dozens of books have been written about this iconic place.

Not Always A Prison

Contrary to what many people believe, Alcatraz Island wasn’t always a prison. Interestingly, it started as a fortress, where the military could survey the surroundings of the San Francisco bay. Furthermore, it was also the perfect place for a lighthouse, which guided boats to the bay for years.

However, during the Civil War, as military officers were put under arrest, Alcatraz started functioning as a military prison. While at first, this was just a temporary measure, the place functioned as a military prison for 73 years.

A Rejected Transition

When the Federal Government announced Alcatraz would become a federal prison, the residents of San Francisco were outraged. People didn’t want a maximum-security prison so close to the city.

Despite it being located in the middle of the sea, there were worries about prisoners escaping and wreaking havoc in the city. People were worried about the well-being of their loved ones and different civil groups organized protests. However, the decision had been made and there was no turning back.

Proving The Escape Route

Approximately 17 military prisoners had escaped the island before. This was one of the main concerns of the residents, as it was not impossible to find a way to leave. Furthermore, two women took to the task of showing how swimming from the island could be done. Doris McLeod and Gloria Scigliano swam separately out of the island as a way to prove this.

They were both successful. There was even a proposal for creating a peace statue instead of turning it into a federal prison. But instead of looking for a designer for the said endeavor, the Justice Department made changes to the existing infrastructure.

New Security Systems

The abundance of security measures made Alcatraz a very difficult place to escape. There were observation towers, which allowed for the surveillance of the whole prison. Furthermore, the doors of each cell were reinforced so that a prisoner could not tamper with them with simple tools.

Metal detectors were installed, and as a way to counter any possible riots, there were tear gas detonators. Previously, there had been a tunnel going under the building, but it was sealed off. The last defense was a natural one, the freezing waters surrounding the island.

The Prisoners

Despite what people think until today, the prison was not used for high-profile criminals only. While famous prisoners such as Al Capone and Machine Gun Kelly spent part of their sentences there, a great number of prisoners were unknowns.

This is because Alcatraz was the place were problematic inmates were sent. Those who had tried to escape other institutions or that failed to follow the rules. This prison was never the first place where prisoners were sent after their sentences in court.

The Anglin Brothers

The Anglin Brothers are an example of two prisoners who were not well-known when they arrived at Alcatraz. However, their names would eventually become legendary. They grew up in a family of 14 siblings, and they were very poor. Together with a third brother, they started robbing banks.

John and Clarence ended up in Alcatraz after they were caught trying to escape their respective prisons. Curiously, they had always attacked the places they robbed after the bank was closed. This was a way to avoid injuring anyone. The one time they used a weapon, it turned out to be a toy gun.

The Safest Place

Aside from the reinforcements made before the opening of the building as a federal prison, there were strict rules in Alcatraz. One of these was that there were around a dozen checks a day, making sure all prisoners were accounted for. Also, there were hard iron bars installed.

The distribution of guards followed a logistic strategy that also maximized surveillance over the entire prison population. Even visiting time, in which the prisoner’s lawyer or family could come, was strictly guarded.

Escape Attempts At Alcatraz

During the nearly 30 years in which Alcatraz functioned as a federal prison, a total of 36 men tried to escape. More often than not, they did it with someone else, which equates to 14 escape attempts. Despite the health hazard the freezing waters represented, these men were willing to risk it.

According to the FBI, 24 of them were apprehended and sent back to prison, six were shot, and two drowned. However, one of the most famous attempts—if not the most famous—was performed only one year before the prison closed in 1963.

Reasons To Escape

When the prison was first inaugurated, there was a harsh rule that most prisoners found unbearable: the rule of silence. Inmates were prohibited from talking to each other. They could only do so during meals and recreation time. Any infractions led to punishment. This had a clear impact on the prisoner’s mental health, and the rule was discontinued before 1940.

Other reasons for discomfort were how cold the cells usually were. They had higher cells being coveted because they were usually warmer. That, as well as the simple fact of being imprisoned, were some of the reasons why inmates tried to leave.

Finding Out They Were Gone

June 12, 1962—the guards were performing the regular morning check. However, their day drastically changed when they discovered that three inmates were missing. John and Clarence Anglin, along with Frank Morris were nowhere to be found. Instead, they had their beds to look like they were in them.

They had even built plaster heads with real hair, which completely deceived the night guards. Immediately after this finding out, the entire prison was locked down. A search for these three men was about to begin.

Who Was Frank Morris?

Interestingly, Morris was no stranger to escaping from prison. He had first been imprisoned for the robbery and his dealings with trafficking drugs. He escaped once before, managing to run away from the Louisiana State Penitentiary. In fact, it took an entire year for law enforcement to capture him again.

After one year of being free, Morris was caught and sent to Alcatraz for his involvement in a burglary. In 1960, he arrived at Alcatraz, where he developed an impressive plan with the Angling brothers.

Setting Up For The Escape

It has been estimated that the escapees had been working on their plan for months. Perhaps Morris’s previous education on escape plans helped. For months, they widened the ventilation duct of Morris’s cell. Their tools were as primitive as they came, sharpened spoons as well as saw blades that had been discarded.

To hide the hole they were making, they used painted cardboard. Somehow, they managed to use the motor of a broken vacuum cleaner as a drill. Morris would play the accordion to mask the noise of their improvised drill. Also, they managed to store different items on the roof of the cell.

Making A Go For It

On June 11, 1962, Clarence, John, and Frank crawled through the hole and went up towards the prison roof. According to investigators, they then used a smokestack to slide down. They had collected more than 50 raincoats, and they used these clothes to make a raft, which they managed to inflate.

They now had to make it through the treacherous waters, all the way to San Francisco bay. Their months of planning had led to this moment. But will they make it?

The FBI Steps In

A prison escape is considered successful only if the prisoners are not caught, and the FBI was not willing to let this one be a success. As soon as they were called in, they started a comprehensive search for the prisoners. There were even checkpoints set up all across the United States.

They were alarmed when they realized these three had a history of escape attempts. Furthermore, they proceeded to interview relatives of the escapees. The FBI wanted to determine if anyone could’ve helped them in case they made it to land. After all, the prisoners would need money to get by.

Searching For Their Remains

Of course, another possibility was that the prisoners had not made it to land. Therefore, boat operators in the Bay were tasked with helping with the search. They were to look for any remains or debris that could’ve resulted from this escape attempt.

The search was not entirely unsuccessful, a homemade life-vest was found at one of the beaches. Furthermore, pieces of wood that could’ve been part of a paddle were also recovered. However, no bodies, shoes or any identifiable items were found.

The Alleged Mastermind

There was a fourth prisoner who was supposed to escape with these three inmates. Allen West stated that he had been the mastermind behind the entire plan. He was very well informed, which made it likely that he was actually part of it.

However, according to him, the space wasn’t wide enough for him to go through. Many people believe that West was scared about their chances of survival. He preferred to play it safe rather than end up at a hospital—or worse.

Never Coming Back

It is believed that one of the reasons behind the sudden closing of Alcatraz was this escape. Only one year later, the prison was permanently closed. Allegedly, the escape caused government officers to take a closer look at the conditions in the prison.

It was found that the infrastructure was lacking in maintenance, and there were numerous issues to be targeted. It was a textbook condition for prisoners to escape. In 1963, the prison closed. Now, even if they were to catch John, Clarence, and Frank, they would never have to go back.

Finding More Affordable Alternatives

Allegedly, the true drive behind the decision to close Alcatraz was the fact that it was the most expensive prison in the federal system. It had stopped being a necessary investment, as other high-security prisons were created. This led the federal government to use other institutions to house these inmates.

Today, Alcatraz is no longer a loss of resources. On the contrary, it has become a major tourist attraction, with a museum visited by thousands every year. Did the closing of the prison mean a stop in the search for the Anglin brothers?

The FBI Makes A Decision

After exhaustive research, the FBI decided it was time to drop the investigation. According to them, the escapees were surely dead. While young people had proven the swim could be done, the FBI believed that the strong currents would have made things terribly difficult for the Anglins and Morris.

Furthermore, the fact that no stolen car had been reported during that time led them to think they had never made it to land. Another one of the reasons why the FBI closed the case was the fact that the relatives of these inmates had no means of helping them.

17 Years Of Unsuccessful Search

It wasn’t that the FBI stopped searching immediately. On the contrary, they looked for these three inmates for 17 years! And yet, there was nothing to be found, they believed them drowned, but many others thought they might have gotten away with their escape.

The FBI sustained that there was no credible evidence that they were alive. But objectively, there wasn’t sufficient evidence to think they were dead either. Even some clothes found later at sea are considered to be another person's.

Insufficient Proof Of Death

There had been different objects found, which could have belonged to the escapees. Aside from the remains of a paddle, three life jackets were found in different areas. One of them was very close to the shore of Alcatraz.

Furthermore, it wasn’t as if they had a raft. The makeshift raft they had made had been put together using binder clips. According to the investigators, there was a strong chance the clamps wouldn’t have been able to hold the raft’s structure once in the water.

A Letter Arrives

In 2013, a letter arrived at the San Francisco Police Department. The letter had allegedly been sent by one of the Anglin brothers, John. He claimed he was the only escapee alive and that he was willing to turn himself in under very specific conditions.

This letter was brought to the FBI for analysis, but the results were inconclusive. Was he truly John Anglin? And why would he be reaching out after so much time had already passed?

A Desperate Plea

According to the letter, Frank Morris had died in 2008 and John’s brother, Clarence, had passed away in 2011. He was all alone in the world and now had cancer. He wanted to turn himself in to be able to get the medication he needed for his disease.

However, he wanted the minimum prison sentence possible, knowing that he was nearing the end of his days. How could the FBI accept this? And did they even believe him?

The Evidence Was Insufficient

After the FBI had dropped the case, it had become the responsibility of the U.S. Marshals to find the escapees. Since the FBI’s analysis of the letter was so inconclusive, they decided that it couldn’t possibly be John Anglin. Their skepticism led them to make no comments about this information.

The news that there was a letter at all didn’t come up until five years later, in 2018. Furthermore, they thought the person writing the later just wanted to be in all the celebrity news outlets. There was a reason for this belief.

The Suspicious Request

One of the things that gave pause to the FBI officers was the fact that the writer of the letter wanted to appear in the news and to make his surrender public. While this might have been a way to get assurances that he wouldn’t be harmed, it doesn’t seem like there would be a reason to fear for his well-being.

Therefore, this measure was hardly necessary. This led them to believe that the writer may have just wanted notoriety. This is something the escapees, if they had survived, had avoided for 50 years.

What Did Alcatraz Look Like?

At the time the alleged John Anglin sent his letter, Alcatraz didn’t look different than when he had been within its walls. However, the lighthouse had been restored, so that visitors could admire the first one that ever existed on the Pacific Coast. Also, the historic gardens had been renovated.

However, the prison itself was so similar to where he once lived that even the hole through which he escaped had been conserved. He would’ve probably been disconcerted to realize how much money the tourism industry makes off his former prison.

A Desirable Prison

Something visitors might be surprised to learn is that many prisoners preferred Alcatraz. Since this was a penitentiary where people were always coming in from other prisons, comparisons were made.

As it turns out, the fact that Alcatraz wasn’t crowded in the least made it attractive to prisoners! Being able to have their own cell was considered a positive point by everyone. Therefore, being in Alcatraz doesn’t appear to be the nightmare portrayed by books and the media.

Best Food In The Country

Another interesting tidbit about what life in Alcatraz would have been for John, Clarence, and Frank is the fact that Alcatraz had the best food in the entire prison system. Therefore, their nutrition was probably better than what they had been getting at their prior prisons.

Furthermore, the guards were also far from cruel. According to former prisoners, they just left them alone and interacted only as necessary. Why then would the brothers and Morris try to escape? And did they have any odds in their favor?

The Feared Dungeons

Alcatraz was far from a vacation spot. Despite it being better than other prisons, it was still a prison. Furthermore, there were dungeons where prisoners were kept during the ‘30s. It is unknown if these were used in the later years or during the stay of the Anglins and Morris.

While it seems very unlikely, knowing that this dungeon existed at all could have caused fear in the inmates. Furthermore, the simple fact that they had a history of trying to escape made them a flight risk. Some people just feel no anxiety when faced with daunting odds, and it seems like these three were exactly like that.

Some Favorable Odds

According to another prisoner, Bob Schibline, the prisoners had tide tables from a Chronicle page. How did he know that? He had given it to them himself! Bob had retrieved it from a wastebasket. This meant that the Anglins and Morris had an idea of what time would be best to try to make it to land.

Furthermore, the Anglins were great swimmers, as they had grown up swimming in Tampa Bay in turbulent waters. This meant that they had sufficient education regarding currents—even if in this case, the water was freezing.

Science Backs The Letter

In 2014, a team of Dutch researchers decided to go a bit deeper on whether or not it would’ve been possible for these three inmates to escape. Using modern technology, they developed interactive models to simulate the overall conditions of the water and the bay when they escaped.

According to them, there was a one-hour window in which it was very likely they could’ve reached land safely. Despite how short that window was, it was still a possibility to be considered.

The Death Of The Third Anglin

A little-known fact is that John and Clarence had a third brother, Alfred. They had all been bank robbers together. However, unlike his brothers, Alfred was on his best behavior while he was in prison. Only months after his brothers allegedly escaped, he was waiting for his parole hearing.

It was very likely that he would be able to leave prison due to his great behavior. However, he did something extremely unexpected on January 11, 1964. Alfred tried to escape, only to be electrocuted by a high-power line.

Adding To The Mystery

Alfred’s departure was disconcerting. Why risk everything and leave a fugitive when he was probably going to be a free man only weeks later? According to his cellmate, Alfred had received a letter from his brothers. This urged him to forget about his model behavior and try to join them.

This was one of the only explanations that could make sense of his unfortunate decision. Another one of his brothers, Robert, stated that during his last visit, Alfred had hinted at the fact that he might have known where John and Clarence were.

A Disappointed Family

When it became known that John's letter had made it to the FBI in 2013, the family members of the Anglin brothers were very upset. They felt they had a right to be informed, especially if their alleged relative was deadly ill. They were very disappointed with the behavior of law enforcement organizations.

It could be entirely possible that one of their own was out there, suffering, without access to the treatment he needed. Also, they had reason to believe the letter might be real.

The Family Had Proof

The tale of the Anglin brothers was part of this family’s DNA. Younger generations had heard all about it, and they knew that there had been occurrences that led the family to believe they might still be alive. One of these was the fact that, for three years, their mother received a Christmas card.

The cards had been signed by Clarence and John. However, the police stated that there was no way to determine if the cards had been signed and sent after their alleged escape.

A Long Shot

The family had more things to say about this. David and Ken Widner were John and Clarence’s nephews. They went public in 2015 and stated that they had reason to believe their uncles were alive and in good health, living in Brazil.

However, this would contradict the letter where John declared Clarence was already dead. Despite this, it has been speculated that he might have wanted the police to think the others were dead to protect them.

A Common Question

Today, the escape of the Anglin brothers continues to be one of the most fascinating subjects when it comes to the history of Alcatraz. The workers there have stated that people often ask them if they think the prisoners could have made it.

Furthermore, one of the most visited places in the former prison is the hole through which they escaped. It seems like people want to believe that human ingenuity can trump any security system, no matter how comprehensive it might be.

They Even Have Their Own Movie

Interestingly, the story was immortalized in 1979, in the film Escape from Alcatraz. Here, Clint Eastwood plays the part of Frank Morris. While the movie took numerous liberties, it helped in making the legendary story even more well-known.

In the movie, Morris knew the Anglin brothers from another prison, something that was not true in real life. Furthermore, they made Morris into a genius who didn’t need high school to know numerous things that helped him plan the escape.

An Unresolved Mystery

Despite the dismissed letter, the mystery of John Anglin, Clarence Anglin, and Frank Morris’ escape remains to this very moment. Likely, we will never know with certainty if they made it out alive.

After all, they would be elderly men by now and would be completely unrecognizable. The U.S. Marshals support the FBI’s claim that these men are dead. However, there’s still the question of why they continue to look for these three escapees if they're so certain about their mortality.

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