Can James Brown escape the iconic prison island— and does he even want to leave?

I’ve never seen my son quite so captivated (no pun intended) as he is now—in the middle of the Alcatraz audio tour. While I fiddle with the headset control and work out how to pause the commentary so I can take in the detail in the old cells, he’s off in a crowd of jail tourists, keen to find out as much as he can.

For a while I was slightly worried I’d lose him, but then I realised—this is a prison on an island that only five inmates ever escaped from, so he’s not going anywhere. And anyway, as history lessons go, he seems to love it. People told me to book early and choose the dusk tour for maximum eeriness, but because of the confusing array of San Francisco day-trip offers online, I did neither. Thankfully we managed to get a boat before the end of our holiday, although you normally have to arrange it in advance. There’s only one boat trip to Alcatraz, and we were very excited to be on it.

The opposite of fort knox, Alcatraz has entered the language as something that’s impossible to escape from. Maybe that’s what makes the escapees’ stories even more fascinating. Five prisoners fled The Rock in two separate breakouts. Two were captured on the next island, while the other three—the subject of the Clint Eastwood film Escape From Alcatraz—are still missing.

The authorities like to say they probably died while trying to swim across the bay, but they’re still on the FBI wanted-fugitives list, which in itself is quite surprising. If they survived, they’d all be in their early eighties now and could be reading this article. In fact, I hope they are.

The prison itself is far smaller than you’d imagine—just two symmetrical blocks of cells with a walkway between them and a view out to the bay for those locked up on the top floors. The exercise yard is the one you see in the film, as are the walkways. The museum audio tour features the firsthand testimonies of some of these prisoners and the warden who guarded them. It sounds like it was as much fun to work here as it was to be locked up.

The living monument to incarceration has lots of stories to tell and myths to bust. The Bird Man of Alcatraz, for example, didn’t have any birds here; he had them at his previous prison. And he wasn’t the gentle soul Burt Lancaster portrayed him as either—unlike “Machine Gun” Kelly who, to paraphrase the tour, “behaved like a total gentleman once he’d put his machine guns down”. 

This in particular impressed my son. “He worked out that by being well behaved in prison he’d get privileges,” he said. “Everyone liked him because he was a gentleman.” Hopefully this is a thought he’ll take back to school with him.

I spent most of our time on Alcatraz wondering what on earth it must have been like surrounded by bars, psychopaths and people with murderous anger-management issues. In the solitary-confinement cell I took a few “art shots” of the ventilation holes and pale-green walls, and wondered what the prisoners must have looked at all day. Having said that, a couple of the tiny cells, with their jigsaws and books, actually looked quite appealing—no council tax or parking tickets to pay, no idiots on the train squealing on their phones. You’d just need to stay out of the way of The Creep, a notoriously unstable sociopathic prisoner who went everywhere on tiptoes.

So many characters portrayed on film were kept here. We see Al Capone in his mugshot, looking cocky and supremely powerful, and Bumpy Johnson, the Godfather of Harlem who was Denzel Washington’s character’s boss in the film American Gangster. Then Frank Morris, who led the trio that escaped from their cells by scraping open the walls and replacing bricks and their own sleeping heads with papier-mâché replicas.

Having walked slowly through the dining hall, the infirmary where The Birdman lived due to ill health, out into the exercise yard and around the warden’s quarters, I caught up with my son outside. He was overflowing with information and questions. But first he wanted to go to the shop and meet a real-life former prisoner who was signing books there. 

I doubt anyone but Al Capone and Kelly would have imagined that, half a century on from their time there, they’d be selling Alcatraz prisoner and prison merchandise  such as the posters, books, fridge magnets, postcards and sweatshirts on sale here.

My son came back with a poster of the most infamous inmates, with hundreds of years of prison sentences between them. “I’m going to put this on my wall with my skateboard posters,” he explains. “This is one of the best places I’ve ever visited.” As prisons go, it’s hard to disagree.

James Brown, founder of Loaded magazine now edits Sabotage Times—an online magazine with the motto: "We can't concentrate, why should you?" Since November 2010 James has written over 50 of his popular monthly Reasons To Be Cheerful column in Reader’s Digest, you can read more by clicking here.

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