Jamie Diaz never stopped dreaming of freedom. Even after nearly 30 years of incarceration, the painter filled canvas after canvas with wings, fresh air, and exuberant queer expression. Now, Diaz no longer needs watercolors to envision life on the outside; just after 10:30 a.m. last Friday morning, she walked out into the Houston rain as a free woman.
Diaz’s release follows the news that she made parole in February of this year, beginning a hazy countdown for family, friends, and fans of the artist, who rose to prominence through a series of comic books and a celebrated 2022 NYC solo exhibition. Last week, the timer finally went off.
Waiting for Diaz at the gate was Gabriel Joffe, the artist’s chosen nephew and closest confidante over the last decade. “It’s tomorrow, it’s less than 24 hours,” Joffe told Them from their hotel room the night before Diaz’s release. “It’s funny, because the case manager called me today to say, ‘Be prepared, you might be waiting in the parking lot for a couple of hours.’ And I was like, ‘You’re talking a couple hours in the scheme of 30 years. I don’t care, I’ll be in the parking lot all day if it means she doesn’t have to wait another moment.”
Joffe, 34, has been looking forward to this day since their first encounter with Diaz back in 2013. At the time, they were volunteering for the abolitionist organization Black & Pink, which connects LGBTQ+ people from within the carceral system to those outside. One Sunday evening, Joffe stumbled upon an unforgettable letter containing both a dreamy illustration and an invitation to write back. Joffe did just that, embarking on an epistolary exchange that would span hundreds of messages, dozens of paintings, and countless calls.
The pair became family — a relationship depicted with warmth and reverence in the documentary short Love, Jamie, directed by the documentarian Karla Murthy. Through a blend of recorded phone conversations, recitations of letters, and footage from the opening of Diaz’s 2022 exhibition, “Even Flowers Bleed,” Murthy’s film offers a stirring portrait of trans kinship and its capacity to transcend even the harshest of barriers.
“This film is a celebration of their relationship,” Murthy tells me. “And the power of art to bring two people together.”
In one of the short’s most illuminating sequences, Gabriel reads aloud from a letter Jamie wrote after beginning hormone replacement therapy. “Things are going fine with the HRT, so you’re right; despite my advanced age, the hormones are working, and I’m gaining amazing results,” Diaz shares. “I’m even starting to tell people that I’m all woman, and I even believe it. I never knew how much transitioning would mean to me, but it is truly me, and I love it. How are things going with you and your T? You look amazing and happy, and that makes me happy.”
The filmmaker grows emotional when thinking of the moment she first heard of Diaz’s imminent release. “A few months [before], I was writing with her and complaining about how much it had been raining in New York, and she [replied] talking about how when she gets out, she can’t wait to stand in the rain,” Murthy says, adding, “That’s what I [began] imagining when we got the release date — her standing in the rain with a big smile on her face.”
On June 3, Love, Jamie will premiere as part of PBS’ Emmy-winning series, American Masters, a point Murthy knows will be especially significant for Diaz. “I'm just so happy that we were able to find this kind of home for the film and to showcase Jamie's talent and art,” Murthy says. “This was her dream. She wants to be known as an artist, and this is the perfect platform for her to make her big debut to America.”
Jamie Diaz grew up in the Houston area of the early 1960s, where she showed early signs of talent as a visual artist. Even as a child, the artist gravitated toward the works of Rembrandt and Vermeer, Dutch masters’ whose use of earth tones and unexpected sources of light would serve as inspiration for her own canvases years later. Diaz’s dreams of being a painter would be put on pause in her early thirties, when a conviction on felony drug charges turned into a life sentence.
These were traumatic years for Diaz, punctuated by all the regular indignities of life in a Texas prison, plus the bevy of hardships stemming from her liberated gender and sexuality. At one point, Diaz sought solitary confinement after she was assaulted on the unit. She also sought psychic safety through her art, which brims with visions of liberation. Looking at Diaz’s wild, effusive, sometimes carnal pieces, you’d hardly think she produced most of her life’s work while incarcerated; that she made her brushes with donated hair; or that the whites of her pictures came from the leftover paint used on prison walls. This is by design; for Diaz, painting has always embodied not just a creative calling, but a method of transportation. “I go all over the world in my mind when I’m working,” the 66-year-old artist told Them, in 2022. “Sometimes I think I even go to other worlds.”
Viewers got their first chance to see the fruits of Diaz’s work in September of 2022, when New York gallerist Daniel Cooney opened the solo show devoted to her comics and paintings. Before the exhibition opened, Diaz joined Cooney, Joffe, and filmmaker Karla Murthy on a call. “I almost feel free,” she said at the time. “Almost, not quite.”
About eighteen months later, in February of 2024, Diaz and her network of supporters learned of her parole. “I couldn’t believe it,” Joffe remembers of receiving the news. “It’s been…” they trail off, struck by the memory. “When I see her walk out, when I have her in my car, and we drive away, that’s when it’ll feel real.”
Unfortunately, the good news was tempered by the reality that the artist had suffered a stroke at the beginning of this year. She’s recovering slowly but surely, says Joffe, who was able to visit Diaz in a Texas Intensive Care Unit. The hospital visit marked the first time Joffe could actually touch Diaz. “It was a little distressing because they have armed guards and she's handcuffed and all this stuff, but we were able to essentially have a contact visit,” they explain. “It was really incredible timing to be able to be there.”
Last week, Joffe got the call they’d been hoping to receive for over a decade; Diaz had a release date — May 31, just in time to enjoy her first Pride as an out trans woman. When the day came, Joffe arrived early, waiting despite the rain for Diaz’s departure. Joffe’s text arrived just after 10:30 a.m.: “She’s a free woman,” they told me. Then, a second message, this one a quote from the free woman herself: “It’s good to be out, alright!”
For their first outing post-release, Diaz and Joffe drove to a local diner, where they enjoyed a brunch of eggs and hash browns before heading to see some art at the Menil Collection in Houston. From there, the pair began the trip to Dallas, where Diaz will be living until hopefully joining Joffe in Denver. Along the drive, they stopped for a makeover at a couple of salons in Oak Lawn, Dallas’ LGBTQ+ district, where they also took in murals of Sylvia Rivera and Martha P. Johnson. On Sunday, Diaz and Joffe attended Dallas Pride and had a “fantastic time,” Diaz said.
“For Pride, I want young trans people to feel encouraged that things are going to get better,” she added through Joffe.
To round out her first Pride as a free woman, Diaz visited a local art supply store, where she had free range to buy her own canvases, oil paints, and brushes for the first time in almost 30 years. She already has her next project in mind, Joffe notes. “Before her stroke, she was talking a lot about doing large format pieces on huge canvases,” they say. “Big oil paintings all about queer love.”
As the weekend came to a close, Diaz and Joffe turned their attention to a handful of logistical essentials, including meeting with her parole officer and applying for social security benefits. “It should be noted that while Jamie is ‘free,’ she is on parole,” says Joffe over text. “Reentry also includes the maze of getting documents set up, learning new technology, and navigating all of this post-stroke.”
The road ahead for Jamie Diaz will be by no means simple or without hardship, though there’s little that can complicate the profound relief of emerging from life behind bars.
“It’s just so beautiful that I can now funnel support for things like medical care and housing because she’s free, ”Joffe says. “There’s already been this community support over the years, and I hope it continues. Her being free isn’t just a period at the end of the story; she’s free, and now we’ll see even more of Jamie.”
For Diaz, that’s the plan. “My freedom feels amazing,” she shares via text. “I’m ready to start more art.”
“Love, Jamie” will be available for streaming through PBS on June 3.