Escaping Alcatraz: 15 Shocking Facts About The Prisoners Who Attempted The Impossible

As one of the most famous prisons to have ever existed, Alcatraz housed the most infamous convicts of its era. It was a fortress that was nestled on an island in the San Francisco Bay, and served a painful reminder to the unlucky men heading there that escaping the prison was virtually impossible. Alcatraz was heavily guarded, and the swim to the shores of San Francisco seemed to stretch on forever. It may be beautiful to look at as a civilian, but those unlucky souls serving their prison sentence there would have begged to differ.

These days, Alcatraz is a tourist spot in the bustling city of San Francisco, and visitors funnel in each day to learn some incredible facts about the prison's rich history. Guided tours are given throughout each day, and guests get to learn about history and famous inmates that served time on the island. Among the more interesting facts about the history of Alcatraz, the attempted escapes always piqued my interest the most. 36 men were bold enough to attempt an escape from the island, and their differing attempts were all unique. Some were incredibly simple, while others were complex schemes that were orchestrated by clever criminals.

Keep in mind that even if these men made it past the guards and to the shore, the 1.25-mile swim that awaited them in the frigid waters of the San Francisco Bay posed the biggest challenge. It's not like the men were all stud athletes who were built for endurance. Their nutrition and lack of resources assured that swimming to San Francisco was a ridiculous notion. Nevertheless, these men gave it their best, and left us with some incredible facts about attempting the impossible.


15 Some Tried Filing Through The Barred Windows

The desperation that inmates felt when arriving at Alcatraz must have been palpable, and the numerous and inventive ways they tried to escape are truly impressive. From the second they stepped foot on the island, each prisoner began to methodically plan out their escape. While some get clever with their methods, others chose a simpler solution. Case in point being when prisoners Theodore Cole and Ralph Roe attempted their escape from the facility.

The two inmates filed through some barred windows, and began their great escape undetected. The two prisoners must have been pretty stealthy, because they actually made it to the ocean. Soon thereafter, they hopped in the Bay, and made a swim for it. Unfortunately, no one ever saw these two again, and conventional wisdom suggests that they died at sea. Nevertheless, give credit where it is due, because even making it that far on the heavily guarded island was no easy feat.

14 Some Even Killed A Correctional Officer


For those who have seen the show Orange Is the New Black, you know that inmates and correctional officers don’t exactly have the greatest relationship. The prisoners have a natural disdain for those who are responsible for keeping them in line, and one fateful day on Alcatraz saw the tension boil over, costing an officer his life. While in prison, inmates are offered a variety of jobs to pass the time and to make money for commissary. In the woodworking shop, Thomas Limerick, Jimmy Lucas, and Rufus Franklin carried out a plan to attack an officer. Using a hammer, the three men beat the officer, and made a run for it. While making a break for it, the men were apprehended.

Limerick and Franklin were shot, and Limerick would die from the wound. The other two men stayed alive, but suffered severe punishment for their actions. Each would receive a life sentence for the murder of the CO.

13 A Few Tried Sawing Through The Cell Bars

They say that the quickest way to get from one point to another is in a straight line, and maybe some inmates took that expression a bit too seriously. While some may have preferred a touch more cunning in their attempted escapes, some just went ahead and went the more obvious route. Back in 1939, there were 5 inmates who all made a run for it, and their attempts began back in the isolation unit in which they were being held. These men chose to cut through their cell bars in order to break free and make their way to the ocean.

After their successful escape, these 5 inmates would make it to the ocean, but alas, that is where their attempt was thwarted. Three of the men waved their white flag when they were discovered, while the other 2 decided to put up a fight. They were then fired on by the officers, and one man even lost his life.

12 A Bolder Attempt In Taking Correctional Officer’s Hostage


The men that have comprised this list so far have had varying degrees of success, and none of them quit of their own volition. Most were either caught or shot by the guards. This instance, however, is a shining example that sometimes the best way to avoid a sticky situation is by using your words. In May of 1941, 4 inmates carried out a plan to take several officers hostage. The men were successful, but their plan never reached its target destination.

While in the midst of their hostage situation, the four inmates began to converse with their hostages. The officer's sharp mind and tongue somehow managed to convince the inmates that this was a terrible idea, and they actually coerced them into giving up. Imagine being so close to tasting the freedom that you have longed for only to be convinced by a hostage that it's a bad idea. The inmates were doomed either way, but just throwing in the towel like that is a bit disappointing.

11 Lack Of Stamina Led To Giving Up On The Swim

Looking back at the history of the complex, I find it puzzling that inmates would actually try to escape from Alcatraz. Sure, you might be able to find a way out of confinement, but the notion that these inmates could make the swim back to San Francisco is outrageous. Sure, people have done it, but these inmates weren’t in excellent shape, and their diets couldn’t have been enough to provide the energy required for the swim. Nevertheless, these feeble-minded men couldn’t resist the temptation of freedom, and gave it a try.

In September of 1941, inmate John Bayless tried his luck at escaping the prison, and to no surprise, was unsuccessful. But, unlike others, Bayless actually made a swim for it once he reached the shore. However, Bayless would turn around shortly after entering the Bay, and swimming back to shore. For his efforts, all Bayless got was wet and embarrassed.

10 Unfortunately, Some Were Shot In The Water


Some of the prisoners who attempted the daring escape of Alcatraz were fortunate enough to actually make it to the ocean. The problem with this feat is that once the inmates got to the shore, the results were never in their favor, and some who dared to brave the waters were taken out by the officers that were responsible for tracking them down. April 14, 1943 saw four inmates make a break for it, eventually reaching the ocean and yielding different results. Two men, Harold Brest and Fred Hunter, were tracked down, caught, and brought back to shore. Another inmate, James Boarman, wasn’t as fortunate, and when officers opened fire on him, he was hit, and would eventually drown.

Now, those three men all had terrible endings to their evenings, but the fourth man almost did the impossible. Inmate Floyd Hamilton was nowhere to be found, and most assumed that he had drowned with Boarman. Surprisingly, Hamilton survived the waters, and hid in a cave near the shore. Eventually, he was captured.

9 Disappearing From Duty

While you are stuck at your job spending time reading lists and not working, do you ever find yourself thinking about your great escape? Legitimately just getting up and walking right out the front door and never coming back? Fortunately for you, no one is going to stop you. Inmates, on the other hand, aren’t so lucky. In comparison to the other entries on this list, Ted Walters’ attempt to escape Alcatraz is probably the least inventive, and unsurprisingly among the least successful.

As the story goes, Ted was on duty when he finally decided that enough was enough, and he decided to just leave. Of course, being stuck on an island did him no favors, and his lackluster attempt to leave fell short. Our dear friend was caught by officers while still on the shore. Call me crazy, but if I’m going to break out of prison, I’m going to be a little more creative than this.


8 Posing As A Soldier


Imagine being so fed up with your living conditions that you are willing to do whatever it took to make changes. So far, we have seen examples of men killing people, breaking iron bars, and even taking hostages to break out of Alcatraz. All of these attempts, of course, were thwarted, but a few of them were pretty clever. This example of cunning could very well top a list of most creative exit attempts. In 1945, inmate John Giles tried pulling off the impossible by using some handy resources. After a load of army fatigues were sent to Alcatraz to be cleaned, Giles swiped a set, put them on, and then headed aboard a ship heading to freedom.

Giles, however, didn’t get the results that he was looking for. The ship that he was on headed towards Angel Island, which housed a military facility. Soon thereafter, the jig was up, and Giles was sent packing back to his home on the island.

7 Cellhouse Takeover

Bloodshed and hostage situations were a part of several escape attempts, but they all paled in comparison to this. A situation which saw several prisoners gain access to weapons, Alcatraz was truly rocked with the events that transpired on May 2nd through the 4th of 1946. It is famously referred to as the "Battle of Alcatraz", and the lives of officers and inmates alike were taken during this bloody battle for prison control. 6 prisoners banded together to gain weapons access, eventually taking a few guards hostage. In the thick of everything, their plan began to deteriorate, causing division between the men. Several hostages were executed, and the Marines were called in.

When the Marines are called in for help, you know that it is serious business. They hit the area with bombs, looking to take the prisoners out. In total, the situation lasted for nearly 2 days, making this escape attempt the bloodiest and longest in the prison's history.

6 Hiding Out In The Rocks 


Serving a life sentence for murder must be a terrible way to live, and inmate Floyd Wilson who had made his way to Alcatraz by way of Atlanta was ready for a change. Each time a ship made its way to and from the island, a muster was called. This provides guards a simple way of keeping track of the prisoners that they are responsible for, and gives an immediate alert that trouble may be around the corner. In one such instance, a muster had been called, and Wilson was nowhere to be found. An alert was put out, and the hunt for the inmate quickly got underway.

After 11 hours of scouring the island for him, Floyd Wilson was eventually found hiding out in the rocks. He was found only 150 yards from where he had originally disappeared from. Wilson was already serving a life sentence, so he had very little to lose by attempting the escape.

5 Floating In The Bay

Not only were these two men unable to pull off successful robberies as civilians, they were also unable to pull off a successful escape as prisoners. Aaron Burgett and Clyde Johnson were both serving lengthy sentences for their robbery attempts in Missouri and Tennessee, respectively, and both were tasked with working garbage detail. The inmates worked together to overpower an officer who was on duty, making a beeline for the ocean. While making a swim for San Francisco, Johnson would eventually be caught. Burgett, however, was not as fortunate as his partner.

It seemed as though Burgett had completely disappeared until his lifeless body was spotted floating in the ocean. A search for his body that lasted for 10 days had already been called off by the prison. This discovery came nearly two weeks after the men had attempted their escape. It was an abrupt end to what was almost a successful escape attempt.

4 A Disappearing Act


Depending on who you ask, some might say that this attempt was in fact successful, and that these men made it back to San Francisco to live a quiet life. Frank Morris, along with brothers John and Clarence Anglin were never seen or heard from again after their cells were discovered empty. Their escape attempt was an incredibly intricate and well-thought-out idea that appears to have been carried out to perfection. The three men used decoy heads to trick prison guards into thinking that they were asleep in their cells.

These men used makeshift drills and wall segments to hide their master plan, and their stash of items that would be used to get them home. They made their own rafts and life vests to help the voyage across the sea. It was a genius idea that by all accounts may have paid off. Their bodies were never discovered, and the notion that they survived is more of an urban legend than anything.

3 Leaving Through The Kitchen Window

Another team up that failed to yield results, these two men gave a valiant effort, but fell short. John Scott and Darl Parker were both serving lengthy sentences for similar crimes (bank robbery), and worked culinary detail together. The two like-minded men conspired to escape together, and simply needed to wait for the opportune time. Not unlike the prisoners that cut through their cell bars, Scott and Parker sawed through the kitchen window to make their way to the shore.

While their fate may have seemed intertwined, the end results for the two men were vastly different. Parker was found with relative ease, as he was merely hiding in some rocks. Scott, however, made it further than his partner. His unconscious body was discovered by teenagers under the Golden Gate Bridge. Impressively, Scott had made it three miles from the shores of his prison. After being captured, both men were taken back to their home on the island.

2 A 50-Foot Drop


Joseph Bowers may not be a household name, but back in 1936, Bowers' name swept through the Bay Area as he became the very first prisoner to ever attempt an escape from Alcatraz. The prison had already been open for nearly 2 years, and all attempts to escape had merely been dreams to those who were incarcerated. After all, standing on the shore of the island and looking back at San Francisco would snuff any semblance of confidence from those who were imprisoned there. But, each story has to start somewhere, and Joseph Bowers elected to be the first man to attempt the impossible.

Bowers was a mentally ill patient who had no friends, and was fed up with his way of living. While working his detail, Bowers made the decision to try and escape the prison by hopping the fence that led to the shore. He was caught and eventually shot by an officer, falling 50 feet to his death.

1 There Is No Recorded Proof Of A Successful Escape

More so than any other fact on this list, the most shocking remains that in the history of the facility, there is no recorded proof that any prisoner successfully escaped the facility. There have been whispers of a few men who made it to the shore and lived a quiet life, but there is no concrete evidence to support this. Alcatraz housed the biggest and the scariest criminal minds that the country could offer, and none of them pulled off this feat. The heavily-guarded facility and ice-cold 1.25-mile swim were simply too much for any man to overcome.

Alcatraz may not be an active prison anymore, but history buffs looking to get a better sense of the terrors of the island are welcome to take guided tours. For those who have never done so, I would highly recommend it. Even as a kid, it completely captured my attention, and has stuck with me after all this time. Just make sure you catch the ferry home, otherwise you could end up like the inmates on this list.

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