Why We Can't Escape Alcatraz

New York Times

11-05-2025

When President Trump recently said he wanted to reopen Alcatraz, to 'lock up the most dangerous criminals and keep them far away from anyone they could harm,' it was hard to know how seriously to take him. The federal government already houses its worst offenders at a supermax prison near Florence, Colo. — the 'Alcatraz of the Rockies' — where Zacarias Moussaoui, El Chapo, Eric Rudolph and Dzhokhar Tsarnaev are held in conditions far more brutal, isolating and inescapable than anything Alcatraz ever had to offer. One day later, the president doubled down, calling Alcatraz 'the ultimate' in terms of being 'very strong, very powerful in terms of law and order,' and referring to the movies about the place and the failed escapes: 'It sort of represents something that's both horrible and beautiful and strong and miserable, weak, it's got a lot of qualities that are interesting.'
What he was trying to conjure, in his associative but effective way, is Alcatraz's continuing hold on the American imagination, its force as a metaphor for a no-holds-barred, publicly retributive form of justice. Alcatraz was and remains as much an idea as a place. James V. Bennett, the director of the Bureau of Prisons for nearly the entirety of Alcatraz's operation as a federal penitentiary, grasped the enduring symbolic power of the island from the start: 'Always when I went to Alcatraz after that first [visit] in 1937,' he wrote years later, 'it seemed to me that this was the place where the legend of the big house in the annals of crime would live the longest and die the hardest. Alcatraz was never without a sense of fantasy.'
'Fantasy' is a strange word to use in relation to a supermax prison, at the time supposedly the toughest ever built, but we understand it intuitively because many of us have participated in it. Anybody who has watched 'Escape from Alcatraz,' or played the video games, or donned the headphones and shuffled through the cell house audio tour, has played a role in the collective maintenance and propagation of the fantasy that is Alcatraz: the most notorious criminals, the harshest conditions, the solid steel doors to the solitary cells, the dummy heads in the beds of those, immortalized in the movie, who escaped in 1962.
Mr. Trump's plans remain unlikely. Beyond the prohibitive cost and decrepit infrastructure, the logistical complications alone are fatal. The island has no source of fresh water, and everything required to sustain life there, from food and water to fuel, has to be brought in by barge or boat. Those practical considerations aren't what the president is talking about, when he floats the idea of bringing a 113-year-old prison back online to house the proverbial 'worst of the worst.' What he's talking about is the fantasy.
The now-iconic cell house, which sits atop steep island cliffs in the middle of San Francisco Bay, didn't start out as a symbol of anything. The main building was built in the early 1900s to house an influx of military prisoners in the wake of the Spanish-American War; it was only after the Justice Department took it over in 1933 that people started talking about how 'escape- proof' it could be. (The early military prisoners had no trouble breaking out of the building; two men escaped within months of its opening in 1912, never to be seen again, and others would follow.)
Amid a Prohibition-era surge in crime, the Department of Justice decided it needed a location to house the gangsters, bootleggers, kidnappers and escape artists that state and lower-rate federal penitentiaries couldn't hold. Alcatraz wasn't the ideal choice, as its limitations were clear, but money was tight in 1933. The building already existed, it could be retrofitted to enhance its security at a relatively low cost, and the notion of the forbidding 'island prison' had a long and easily-summoned history in the public imagination.
When the federal penitentiary opened in 1934, with the arrival of Al Capone in August from Atlanta and Machine Gun Kelly in September from Leavenworth, the notoriety of the prisoners and the stated mission of the place brought an intense level of scrutiny from the general public. The Bureau of Prisons' direct instructions to Warden James Johnston, in the face of this interest, were to cultivate an 'air of mystery' about the prison's operations and rarely respond to press or other inquiries. With a few exceptions, Warden Johnston followed this policy for the first 12 years of the prison's operation.
When inmate Henry Young was brought to trial in San Francisco in 1941 for the premeditated murder of a fellow inmate, the jury and newspaper-reading public were prepared to believe the undeniably perjurious testimony of the inmates who spoke in Young's defense. Inmate after inmate took the stand and told terrifying stories of torture and deprivation at the hands of brutal prison guards, over the repeated objections of the government's lawyers. This led to Young's conviction on a lesser charge, on the grounds that Alcatraz was the true culprit; the foreman of the jury went so far as to call for a federal investigation into the prison's operation after rendering the verdict.
Much that was said on the witness stand was not true, but the nation had been exposed to the possibility that it might be. The bureau's policy of never setting the record straight allowed wilder and wilder tales to proliferate as time went on: the Island had driven Capone mad! (He was suffering from late-stage syphilis). The legend and mystique, which the bureau had originally tried to cultivate for its deterrent effects, had jumped the tracks and become unmanageable. By the time the administration tried to correct public perception, it was already too late.
A crucial element in the prison's mythology was its unavoidable presence in the middle of the Bay. There it sat for all to see, its powerhouse pumping out thick black smoke as lines of men walked to and from their jobs in the factories twice each weekday. People paid to view the island through telescopes from Fisherman's Wharf, hoping to catch a glimpse of somebody famous. When the escape siren sounded, which it did rarely but just enough, the entire bay became an amphitheater. During a brutal attempted break in 1946, when several convicts managed to get their hands on two guns and cause 48 hours of mayhem inside the cell house, the gunfire and grenade explosions around the prison could be seen and heard from the mainland. Traffic slowed on the Golden Gate Bridge and cars parked three deep from Russian Hill to Coit Tower as the siege played out. Spectators sat out in the parks and on sidewalks to watch the action, a death match in real time, like the picnickers at Bull Run during the Civil War.
That proximity to the city, and the city's proximity to the prison, cemented the public's connection with what went on there. No matter how mythically brutal a prison might be, it won't hold our attention if it's in Florence, Colo., because we can't see it, can't see ourselves in it and it can't see us. Many who take the audio tour on Alcatraz are struck by the same moment: the prisoner who describes being able to hear the dance band, the clinking of glasses and the women laughing at a yacht club across the bay on New Year's Eve. For a second we feel like maybe we can understand what torture it must have been to lie there and listen. A boundary in time and space briefly becomes permeable, and then we get to go back to being ourselves again.
Alcatraz was full of such paradoxes, the escape-proof prison that wasn't actually escape-proof. (The three escapees who made it out of the prison and into the water sometime on the evening of June 11, 1962, are presumed to have drowned, but nobody has proved that they did and they had several hours' head start.) Alcatraz was also a much more humane place than its legend suggests. Yes, it was the end of the line, and as such it was a place of strict routine, restricted privileges and sometimes harsh treatment, but prisoners would tell you that it was the mundane monotony of the place, not the tough conditions, that made doing time there challenging. Even the men in isolation in D Block remained in touch with the rest of the block, where other prisoners could hear their voices, monitor their treatment and even sneak them contraband sandwiches and cigarettes. No such luck for the men locked up in Florence today, who are in lockdown 23 hours a day, have almost no ability to see or connect with another human being and would probably give their arms to serve at Alcatraz as it was.
The administration on the island and at the Bureau of Prisons cared about the men more than you might expect. They met with them, listened to their complaints, encouraged them and wrote their families thoughtful and even misleadingly positive letters to keep minds at ease. Many inmates became so accustomed to the routine on Alcatraz that when they were transferred to other prisons — a reward for good behavior — they asked to go back. As Harry Radkay, who was housed next to Machine Gun Kelly, put it, 'If you minded your own business and did your own time, no one bothered you.'
This is not the Alcatraz that they show you on the tour, nor is it the Alcatraz that the current administration has in mind when it contemplates reopening the place. When Mr. Trump mentions Alcatraz in the same sentence as Sing Sing, a similarly ancient prison in New York, and then refers to 'the movies,' the jig is mostly up. He likes Alcatraz, the Big House of big houses, because it has the right look, the right image, the right clientele and it's right in everyone's faces — his sweet spot.
Underneath that, though, one senses a powerful nostalgia for something that never actually existed: a simpler time, a black-and-white movie, a fertile seedbed for the Manichean atavism that has always powered his messaging. Whether he can create what would inevitably become a casino of human misery on the island isn't really the point. He plants the seed, knowing that our fascination with Alcatraz, developed over the years by the same myth- and moviemaking that influenced him, will supply the rest.