The Life of a Transgender Prisoner
Illinois Department of Correction photo of Deon “Strawberry” Hampton, a transgender woman serving a 10-year sentence for burglary.

The Life of a Transgender Prisoner

Henry Higgins
Henry Higgins
5 min read

Last month’s school shooting in the suburbs of Denver, Colorado, claimed the life of an innocent child. Eight more were injured. In the way that this crime affects the victims and their families, the tragedy is similar to many previous incidents. But it also uniquely highlights a criminal justice challenge that has been the subject of debate: what to do with transgender criminals?

In the UK, where prisoners are classified primarily according to a policy of “self-identification,” recent controversy has focused on Karen White, a violent transgender woman who was moved to a male facility in 2018 after being accused of sexually assaulting multiple female prisoners. In the United States, where prisoners generally are classified according to their biological sex, the issue has been less prominent. However, that may soon change.

One of the two suspected shooters in Colorado is listed in court records as Maya McKinney, a 16-year-old female. However, the suspect now identifies as “Alec,” and has asked that male pronouns be used in all official proceedings—even though Alec is being housed in a female detention center. Social justice activists are demanding that neither the media nor the court “deadname” Alec by referring to the defendant’s legal and biological identity. The case, and others like it, may eventually push the United States to allow more trans prisoners to be housed in prisons that accord with their gender identity.

However, as someone who spent many years in several different U.S. prisons (I am writing under an assumed name), I can attest that, notwithstanding our society’s newfound respect for trans rights, the prison system is very much not built for gender fluidity. Even if Alec elected to go to a male prison following a conviction, granting that request would require all precedent to be overturned, if only for reasons of safety. His female anatomy would make him a rape target. Releasing a vagina of any variety into a land of deprived and often depraved men isn’t something any humane or reasonable warden would allow.

What’s life like for imprisoned transgender convicts? In the case of men who identify as women who are incarcerated in men’s prisons, they are more likely to be put in solitary confinement than the average prisoner. One might assume that this is a step taken to protect them from bigoted prisoners and redneck guards. But this was not my experience (though bigotry and violence are, of course, a real fact of life for everyone in prison). Many trans prisoners I met had some connection to the sex trade before (and during) their incarceration, and sometimes were scarred by the trauma and medical conditions associated with that life. Insofar as their treatment by other prisoners goes, however, transgender prisoners typically live fairly well. They have a monopoly on the rarest thing inside prison: something resembling heterosexual sex.

I met about a dozen men living as women during my 10 years upstate. There was at least one in each of the various prisons I passed through. No one called these people “transgender.” They were called “shemales” by their admirers, the usual homophobic slurs by their detractors, and “lizards” by old-timers. (I’ve been out of jail for five years. Maybe by now younger prisoners have the lingo right.) The ones I knew best were Juwanna, who was a foot taller than me and braided my ponytail; and Kitty; known for taking drugs on credit, and then signing in to protective custody when it was time to pay (in kind).

Transgender convicts receive treatment from other prisoners that correlates to how attractive they are. Kitty had a mane of blond hair, blue eyes, lips reddened with kool-aid and a tight uniform. When she made her entrance into the kitchen holding the frail hand of a certain 80-year-old Mr. Katz, she announced, “It’s us, Kitty-Katz!” This got an ovation. “Jennifer Lopez,” as she called herself, was the star of another facility and known as the girlfriend of the head of a statewide gang. However, not everyone was as lucky: No one wanted to sit next to poor “Grandma” in one joint, her odd and dowdy appearance being the subject of mockery. Meanwhile the same men who called her a “fag” made sure Gigi—another trans prisoner in the same institution—had free drugs, sneakers and food. She was 22, pretty and on female hormones. Gigi had many fans, even though her ID card said Gilbert. Men fought for the right to comb her hair in the yard. Affairs were common, but transactional and generally loveless. Juwanna was known to flash her amazing silicone rack, but not for free. And yes, it was impressive.

The most open forms of discrimination I saw against transgender prisoners were typically committed by neophyte Muslims—recent converts who felt they had to follow the Koran literally. Usually, the older guys would tell them to “let the lizards be.” Fighting a transgender convict was a guaranteed loss. If you won, you just bullied a “tranny.” If you lost, well, you got beat up by a “tranny.” Since they’re the women of male penitentiary, it’s the moral equivalent of wife-beating.

The convicts with boobs had their own separate time in the showers and generally weren’t required to double bunk. The doctors followed the law when it came to their access to medications, these precedents having been set by judges long ago. The social dynamic in female prisons no doubt is different from what I am describing here. But as with trans women in male prisons, Alec will get the hormones to which he is legally entitled (though in some jurisdictions, you get such access only if you were taking the hormones at the time of your arrest).

In late 2018, trans woman Deon “Strawberry” Hampton was transferred to a female Illinois prison after she complained of sustained brutality from guards and other prisoners at a male facility. But getting such an accommodation is rare in the United States, and likely reflects the especially cruel treatment that Hampton received. In general, simply declaring that you are no longer a man does not allow you to move to a female prison. Since Gigi, Kitty and Juwanna all had their original swinging equipment, they did their time with men. From what I could tell, they had few complaints—even if other trans prisoners are treated shamefully. Gigi, in particular, told me that in prison she felt like the belle of the ball.

I wonder whether Alec, if convicted, would really want to spend time in a male prison—because regardless of what pronoun he uses, he would be shocked by the sheer maleness of life in a place full of horny men. When I worked at the library in one prison, I once had to beg a fellow called Dirty Tommy to stop selling hand jobs under the tables while I did my work. He was doing it so close to me that I felt practically involved, and he counted on me not snitching on him. (He nominally agreed to my request but was back hustling the next day.)

Though Alec likely will never see the inside of a male prison because he has a vagina, he should be warned tough butch lesbians run the yards of female prisons with the same ruthlessness as men. Guards who have worked in both kinds of prisons have told me that the ladies can be more vicious in some cases, using the same rough methods to gain status, drugs, money and sex. And it’s hard to say whether male hormone therapy will help Alec in that kind of arena—or make him more of a target.

In any case, if doing your life sentence as Maya when you prefer Alec is the worst consequence of jail life, he’ll be lucky—far luckier, certainly, than his alleged victims.


Henry Higgins

Henry Higgins is the pseudonym of a writer who served time in various American prisons.