On the night of 11 June 1962, in America’s premier maximum-security jail, three convicted armed robbers detached airshaft grilles whose rivets had earlier been replaced with soap. The shafts had been enlarged using an electric drill improvised from a stolen vacuum cleaner motor; accordions smothered the whine of the drill during what must have been some very raucous music hours. Leaving behind plaster-cast imitations of their own heads to fool the guards, Frank Morris and the brothers John and Clarence Anglin climbed up the ventilation shaft and emerged onto the roof. The sight that greeted them didn’t bode well for their escape bid: the jail was built on a small island. Black water lapped in every direction, the moonlight reflecting off the swells rolling in from the Pacific Ocean. The nearest landfall was over a mile away in the brightly lit, heavily populated heart of San Francisco. Morris and the Anglin brothers stood on the roof of perhaps the best-known prison in the world: Alcatraz.
Alcatraz Island, its name deriving from an archaic Spanish word for ‘pelican’, is a small, rugged outcrop in San Francisco Bay known locally but unimaginatively as the Rock. Today it is a national park, the home of guillemots, cormorants and gulls. The jail itself is a museum. Built in 1861 to house prisoners from the American Civil War, it was a federal penitentiary from 1934 until its closure in 1963. Its inmates included some of America’s most notorious criminals, such as Al Capone, the Chicago gangster behind the St. Valentine’s Day Massacre, and Robert Franklin Stroud, the psychopathic ‘Birdman of Alcatraz’ who spent 42 years in solitary confinement.
Undeterred by the bleak outlook from the prison roof, Morris and the Anglin brothers scaled the fence and reached the island’s north east coast. They assembled a raft from plywood and prison-issue raincoats and pushed out into the dark, treacherous bay. The water was frigid, the current against them. The three escapees were never seen again, although debris from their raft was found on a nearby island. Investigators concluded that they had drowned in the turbulent waters of San Francisco Bay. It was the nearest anyone ever came to escaping from Alcatraz.
This daring and ingenious bid for freedom was the subject of the 1979 thriller Escape from Alcatraz, with Hollywood legend Clint Eastwood in the lead role of Frank Morris. Occasionally atmospheric but largely formulaic, and surprisingly devoid of tension for its source material, the film’s greatest interest lies in its window onto life in Alcatraz. The plot follows the real-life escape attempt, including the uncertain ending. Escape from Alcatraz opens with Frank Morris being taken in a launch across the choppy waters of San Francisco Bay to the Rock. A long, silent sequence shows the extensive security precautions at the supposedly watertight prison. The sequence ends with Morris getting locked into his tiny cell. A guard breaks the silence with a sarcastic greeting: “Welcome to Alcatraz.”
Thirty-one years on from Morris and the Anglin brothers’ escape attempt, on 31 December 1993, and 1,700 miles east in Falls City, Nebraska, an incident took place that, had the jail still been open, might have landed its perpetrators in Alcatraz: ex-convicts John Lotter and Marvin ‘Tom’ Nissen murdered a youth known as Brandon Teena—or, as the relevant birth certificate would have it, Teena Brandon.
Brandon was a young woman from Lincoln, Nebraska, who began identifying as a male during high school. After trouble with local authorities she moved to Falls City, where—dressing as a man—she entered Lotter and Nissen’s social circle and began dating a childhood friend of Lotter’s, Lana Tisdel. A spell in a women’s jail for forging cheques alerted Lotter’s circle to Brandon’s nebulous sexual identity. During a drunken party on Christmas Eve Lotter and Nissen stripped Brandon naked. She was then taken, with chilling irony, to a meat packing plant and raped. Brandon defied the men’s order to be silent and filed a complaint. On New Year’s Eve Lotter and Nissen returned to the house where Brandon was staying and shot her.
Like the Morris gang’s escape from Alcatraz, Brandon’s killing and the sequence of events that preceded it also spawned a feature film. Boys Don’t Cry is dour but gripping cinema, driven by a magnificent performance from Hilary Swank who deservedly won the 1999 Best Actress Oscar for her portrayal of the emotionally troubled, sexually confused and physically abused Brandon. Just as Escape from Alcatraz gives cinemagoers a glimpse into the hidden world of America’s highest-security prison, Boys Don’t Cry does the same for the shadowy milieu of transgender sexuality and the repercussions that can occur when society’s unspoken sexual boundaries are violated.
Just as Escape from Alcatraz gives cinemagoers a glimpse into the hidden world of America’s highest-security prison, Boys Don’t Cry does the same for the shadowy milieu of transgender sexuality and the repercussions that can occur when society’s unspoken sexual boundaries are violated
Brandon endured a life sentence of sexual misery: a victim of incest as a child, plagued by gender insecurity as an adolescent, raped and murdered as a young adult. Sex defined her every moment; she spent her entire life trapped in a hidden prison just as escape-proof as Alcatraz. When Brandon emerged from her mother’s womb, the doctor who delivered her may as well have held her up, slapped her backside, and uttered a sarcastic greeting: “Welcome to Sexcatraz.”
 By referring to Brandon by birth name and gender I am not implying any criticism of her choice to present as a man. The English language rigidly enforces orthodox gender orientation; this is itself an indicator of our narrow view of human sexuality. Carolyn Gage’s insightful essay, The Inconvenient Truth about Teena Brandon, articulates “the issue of pronouns” when describing such lives. But the times they are a-changing: in 2015 a gender-nonspecific pronoun was added to the official Swedish dictionary.