Sitting in a grid-like maze of locked metal cages at San Quentin State Prison, I’m surrounded by killers casually eating lunch and talking. I feel anxious and unsettled as I wait in Cage No. 7 for one of Orange County’s most notorious murderers to be brought down from the new psychiatric unit.

The correctional officer leads a groggy and puffy-eyed Skylar Deleon into the cage and uncuffs her hands. I’m not shocked by the transgender inmate’s new, more feminine appearance; I’ve already seen photos of her smiling and posing with a male visitor on Facebook and hardly recognized her.

Although she isn’t wearing the eye makeup and lip gloss from the photo, the heavy beard stubble I saw the last time we talked, in 2009, is gone, the result of the hormones and testosterone-blockers she takes. Her short masculine haircut also has grown long enough for her to wear a side ponytail that hangs below her small breasts.

We say a quick hello, and before we get started, I buy her a quesadilla and two avocados out of the vending machines, which gives me a few minutes to settle into this surreal scene. Our last interview was at the men’s county jail in Santa Ana, just before she was sentenced to death for tying Tom and Jackie Hawks to the anchor of their yacht off Newport Beach in 2004 and throwing them overboard—alive. We met four times over two weekends, during which Skylar listed all the mental health diagnoses and medications the doctors had given her. We also talked about her attempt to slice off her penis with a disposable razor, which landed her in a community hospital.

My visit this May was prompted by a federal judge’s ruling ordering the state of California to provide sexual reassignment surgery to a transgender female inmate housed at the men’s Mule Creek State Prison. A transgender inmate housed in San Diego who has been denied the surgery also has filed a lawsuit in federal court. Those cases might trigger new claims by inmates such as Skylar Deleon—because there are a surprising number of inmates like her.

I’d hoped to talk to Skylar about her hopes for getting the surgery now that the courts had opened this legal door. I wanted to hear about her life on death row and in the psych unit that opened in October. And I wondered if she’d say she felt any remorse for the murders that put her here. So we exchanged letters, and she put me on her visitor’s list. She wanted to talk face-to-face.

During our 2½-hour conversation, she seems calmer and, frankly, more lucid than I’ve ever seen her. Unfortunately, I can’t reveal her answers to my questions. At the request of her attorney—who objected by letter after the interview and discussed his concerns with an Orange Coast lawyer—I must tell this story through my own observations and other sources, because he maintains Skylar doesn’t have the legal capacity to consent to an interview (and neither does he).

I notice that Skylar no longer has body hair, and that she’s wearing women’s socks and a sky-blue top over her bra.

I also see her sneakers are laced up with a plastic bag rather than shoelaces, which inmates sometimes use to hang themselves. Finally, I see that the pale skin of her forearm is scarred by a series of vertical reddish-brown welts. My sources tell me she has frequently cut herself with razors and otherwise harmed herself over the years, resulting in multiple trips to a state mental health facility in Vacaville, as well as to the prison’s acute-care unit.

“She ran full force into a metal door and knocked herself out, every other week, just to get attention and to get up on the fourth floor, the medical crisis-bed unit, to get people to talk to her and to talk to them,” a correctional officer tells me, asking to remain anonymous for fear of losing the prison job.

But these days, Skylar seems to be doing better than she has for some time.

“She’s in good spirits. Last time we talked she seemed real happy,” says William Harder, the friend of Skylar’s and murderabilia dealer who posted Facebook photos of himself with Skylar after one of their regular visits. “She’s not down, or hurting herself, or talking about hurting herself. She seems to be … listening to her doctors and doing the program they’ve set forth for her.”

As soon as the federal ruling was issued this April, Skylar began talking about pursuing state-funded surgery for herself. But this is hardly a new quest; she has wanted such an operation for more than 20 years. Unknown to many people who followed the Hawks case, Skylar’s need to pay for the surgery was a primary motive for murdering the couple.

At this point, you might be spitting out your coffee as you consider Skylar’s quest for state-funded surgery and thinking, “Not with my tax dollars!” And you certainly wouldn’t be alone. Some people, including Jackie Hawks’s mother, believe that once a person kills another human being, that person should lose all civil rights, including the right to be treated humanely.

“Oh my God, I’m sorry, this world has gone to hell in a handbasket. I can’t believe that,” Gayle O’Neill says when I recount my visit with Skylar. “Why don’t they just put her in the (death chamber) … and do what they said they were going to do? My daughter is gone and she didn’t get to do what she wanted to do with the rest of her life, and Tom, either. Why should (Skylar) get to do what he wants to do?”

David Byington, the now-retired Newport Beach police sergeant who worked the Hawks case for five years, has a similar reaction. “He/she is a coward and does an injustice to those people who are actually suffering with the daily challenges of gender-identity issues,” Byington says, adding that after killing three people, Skylar, “the murderer, doesn’t deserve the political correctness (or respect) to be called ‘she.’ ”

I don’t much like the idea of my tax dollars going toward relieving a killer’s emotional pain, either. But the Eighth Amendment to the U.S. Constitution prohibits “deliberate indifference” to the medical needs of inmates—even death-row killers such as Skylar—and requires that they receive “adequate medical care.”

This complicated legal debate has been raging not just in California courts, but also in Massachusetts and Georgia, making it a hotly contested national issue. While one case was pending U.S. Supreme Court review, the U.S. Justice Department weighed in on another, advocating for transgender inmate rights.

“Failure to provide individualized and appropriate medical care for inmates suffering from gender dysphoria violates the Eighth Amendment’s prohibition on cruel and unusual punishment,” the department wrote in February on behalf of a transgender female inmate who sued Georgia’s prison system. “Gender dysphoria is a serious medical condition for which treatment is necessary and effective.”

The primary battle has revolved around the question of whether such surgery—typically to remove the penis and testicles and build a vagina—is “medically necessary” to relieve inmates’ emotional and physical pain, or if hormone therapy and counseling alone are “adequate.”

These prison lawsuits have been unfolding against the backdrop of an escalating gender-identity discussion that has grabbed our attention for much of this year, thanks to Olympic athlete Bruce, now Caitlyn, Jenner. As she transitioned publicly and in real time, she raised awareness and high emotions around the world. We watched her talk and cry as Bruce on prime-time television about her lifelong hardships and her goal to help other transgender people find the courage to stop living a lie amid bigotry. Then we saw her debut her new identity as Caitlyn on Vanity Fair’s July cover, exploding across social media with full breasts and long hair, wearing red lipstick and a satin corset. Her reality TV show “I Am Cait” launched in July.

That series of events brought the transgender conversation out of the shadows and into the mainstream media, sparking questions about acceptance and compassion, the proper terms and pronouns to use, and confusion over the differences between gender identity and sexual orientation, which are separate and unrelated issues. There also has been discussion about the treatment choices of some transgender women, including Jenner, who say they can still feel feminine with their penises intact.

Which brings us to the topic at hand. Should a convicted killer, especially one on death row, be granted such a remedy to relieve pain and suffering—a costly operation that many law-abiding citizens on the outside can’t afford? Especially if that convicted killer committed murder to pay for it?

I didn’t sleep much before my first interview with Skylar in 2009, worrying I might say something that compelled her to put a hit out on me, as she tried to do—from jail—on her father and cousin to keep them from testifying against her. But she never seemed upset by my questions and seemed to enjoy talking about her attempt to cut off her penis in jail, recounting how she didn’t get as far as she wanted because she only had time to cut around the base. As we chatted, she giggled and sang “That’s Amore” to me.

Despite Skylar’s disarmingly gentle and high-pitched voice, I know too well the horrors she has caused. A year before murdering the Newport Beach couple, when Skylar was serving time for armed burglary, she took $50,000 from cellmate Jon Jarvi for some scheme, then cut Jarvi’s throat and left him to bleed out on a roadside in Mexico, all while on work furlough from the Seal Beach jail for the day. Returning two hours past curfew that night, she used part of the spoils to buy herself an anal sex machine from the jail’s computer. Skylar was convicted of all three murders.

I didn’t sleep much the night before my visit this year, either. I also hesitated before bringing her a plastic fork-spoon and knife to eat the vending machine food I bought her for $9.50 in quarters. (Buying food for an inmate is a customary practice when visiting, because it’s better tasting than what they normally get, and they aren’t allowed to touch money.)

Yet, as I sit across from the new Skylar, this more effeminate killer seems more at ease and less threatening than before—even without the protective barrier between us that we’d had in Santa Ana.

Skylar already told me that she has identified as female since childhood but was forced to live a lie for many years. She previously recalled a harsh scolding by her father, former U.S. Marine “Big John” Jacobson, after he discovered young Skylar was dressing up with the neighborhood girls and wearing mascara. “You want to be a girl? I’ll treat you like a girl!” yelled the man for whom Skylar was originally named John “Johnny” Jacobson Jr.

Big John, who threw Skylar down the stairs and shoved toothpicks under her nails after she bit them, spent time in federal prison for drug trafficking. When he got out, Skylar told me years ago, he forced her into being a child actor. Skylar had a pretty face even then, landing some commercials and a couple of non-speaking roles in the Saturday morning kids’ show “Mighty Morphin Power Rangers” during the 1993-94 season. But looking back, she said, she always hated the work and never got to keep the money she made.

Skylar carried her father’s name until just before she started dating Jennifer Henderson in Long Beach in 2002, when she went to court to formally change it to the gender-neutral Skylar Deleon. At the time, only Jennifer knew about Skylar’s desire for the surgery; Jennifer’s parents, faithful evangelical Christians, wouldn’t have understood.

Skylar loved Jennifer so much she married her in two ceremonies before they had a daughter, Haylie, whom Skylar and her pregnant wife later brought on board the Well Deserved in a stroller to gain the trust of the Hawkses. Pretending the Deleons wanted to buy the yacht, Skylar and two cohorts asked the unwitting couple to take them out for an open-ocean trial run. The Hawkses were never seen again.

Skylar has been categorized by state officials as transgender, but privacy laws prevent them from discussing individual inmates’ medical issues in detail. While Skylar’s psychosexual background, gender identity, and mental health issues didn’t play a role in the prosecution’s case, she did draw media attention for coming to a pretrial hearing wearing a women’s jail jumpsuit and makeshift mascara, and later for looking increasingly frail and effeminate.

I dove into these topics after Byington, the Newport Beach detective, told me part of Skylar’s motive for killing the Hawkses was to get money to pay for a sexual-reassignment operation she’d scheduled for two weeks after the murders, in November 2004.

At the time, Skylar and her wife were deeply in debt and living in Jennifer’s parents’ converted garage in Long Beach. Skylar already had put down a $500 deposit with a Colorado doctor to get the operation; she couldn’t cover the $15,000 balance. Skylar and Jennifer came up with a scheme to pay for Skylar’s operation and settle some sizeable debts by killing the Hawkses, stealing their boat, and pillaging their bank accounts.

A correctional officer recalls that when Skylar heard about the ground-breaking court ruling in April, she was visibly excited and shared her renewed hopes with prison staff.

“I saw on the news that a trans inmate at Mule Creek is getting surgery,” the officer recalls Skylar saying. “This is great, because this means now I can get my surgery.”

She also discussed the development with her friend Harder and asked him to send her news reports so she could learn more. “It’s obviously a relief for Skylar because she’d planned to pay for the sex change operation herself. Now, apparently, this changes the game a bit,” Harder says. “(Skylar) has told me she feels trapped. She identifies with the opposite sex (to which) she was born.” (Skylar has been engaged to two different women since she has been on death row; her current fiancee reportedly has offered to pay the basic surgery costs.)

But as with everything else in this story, this is more complicated than it seems. So far, no inmate has had the surgery while in custody in California, where 385 transgender inmates are taking hormones; all but 22 of them are in men’s prisons. Nationwide, officials know of only one inmate—now in California—who has had the procedure done while behind bars in Texas.

The Transgender Law Center—which represents Michelle-Lael (Jeffrey) Norsworthy, the Mule Creek inmate who in April was granted the right to state-subsidized surgery by a federal judge—argues that the state’s “blanket” policy to deny such operations to transgender inmates is unconstitutional.

“No one should be denied the medical care they need,” said Kris Hayashi, the center’s executive director, in a written statement. “There is a clear medical consensus that health care related to gender transition is necessary—and lifesaving—for many people. This decision confirms that it’s unlawful to deny essential treatment to transgender people.”

State officials say the Transgender Law Center is mischaracterizing the state’s policy. In late May, Joyce Hayhoe, a spokeswoman for the receivership agency overseeing medical care in California prisons, said: “Under our regulations we are not allowed to perform surgery that is not medically necessary, so that is what the argument is right now before the court.”

In general, one of the prerequisites for a transgender woman to have the surgery is a diagnosis of gender dysphoria, which Skylar has received. Others are to “present” as a woman for a number of years, which means dressing and acting like one, being on female hormones, and receiving intensive psychological therapy. Although Skylar seems to have met these basic prerequisites, she apparently lacks the state’s “medically necessary” recommendation.

Complicating matters is that prisoners must have surgery at a community hospital, where they must be guarded around the clock by at least two state correctional officers. Hayhoe says the total cost would vary depending on an inmate’s needs, but with security, hormones, evaluations, counseling, and follow-up care, it could reach as high as $100,000.

“It’s more than one procedure” and likely “more than one visit to the hospital,” Hayhoe says. In general, she adds, inmates may pay privately for some types of procedures, but they would still have to be approved based on security concerns.

With nearly 750 condemned men and women in California today, and no executions since a moratorium was issued in 2006, the chances of Skylar living out her natural life are pretty high.

And, like it or not, says Skylar’s friend Harder, “when you put a person in prison you have to agree to take care of them. That’s what the law says. You have to feed them, clothe them, you have to give them medical care. … This is America, and we’re guaranteed certain liberties here.”

As he also points out, we don’t always get to choose how our tax dollars are spent. “I firmly oppose the death penalty,” he says. “Why should I have to help pay for a new death chamber?” If you really don’t want your tax dollars used for sexual reassignment surgery for inmates, he says, then maybe “you should move to a country where they put people like that to death. Then you won’t have to worry about it anymore.”

About the Writer

Caitlin Rother is the author of “Dead Reckoning,” a 2011 book about the murders of Newport Beach’s Tom and Jackie Hawks. During her five years of book research, she attended three trials, combed through thousands of pages of court documents and police interview transcripts, and conducted hundreds of interviews. You can read more about her and her other books at caitlinrother.com.

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