(gentle music) (gentle music continues) - I was a volunteer for this organization and we would get mail from LGBT people that are incarcerated across the US.

So it's hundreds and hundreds of letters.

Because of the sheer amount of mail, we can't respond to every single letter.

But around January 2013, I open up a letter and I've never seen anything like this.

The art just really captured me.

So when I responded, I included my personal home address in case she wanted to write back, and she wrote back.

"Dear Gabriel, I hope all is well in your world.

Thank you for your kind words about my art.

I'm really a surrealist, abstract figure painting kind of artist, but I love illustrating my letters with my cartoons, comics, and, of course, about 90% of my art is queer related.

I'm 55 years old.

I became serious about art at age 15 when I took art in the ninth grade.

But for the most part, I'm predominantly self-taught.

Please feel free to write, and if you have any questions at all, I'll answer them.

Thank you again for your kind words and thoughtfulness.

James."

I don't think initially I knew what our friendship would become.

I mean, I don't think any of us do when we meet someone.

You know, 2013, yeah, like, a decade is a long time and, like, so much has changed for both of us.

(gentle music continues) It's also such a short amount of time when you think of, like, she has a life sentence.

(gentle music continues) (pen scratching) (gentle music continues) (birds chirping) "Dear Gabriel, hey, I'm just sending you these few lines to see if you're all right.

Please use enclosed stamped envelope to send me a note.

Hi, it's great to hear from you again.

Thank you for sharing pieces of your life with me.

This is my 18th year of incarceration.

I'm in prison for robbery and a drug habit, but mostly for being stupid and making bad decisions.

If you don't mind, I'd like to get this free color catalog for trans and cross-dressers, but the advertisement only shows a website and phone number.

Could you have me put on their mailing list?"

(gentle music) In the commissary, she was able to get those little trays of watercolors that you kind of use as a kid with those little plastic brushes with the plastic bristles.

But then she was able to get real watercolors and make her own brushes with real hair from people she met inside.

(gentle music continues) "I'm working on a small collection of what I call my real art for you.

I hope you'll like them.

Your friend James."

(gentle music) Some of the white on her paintings is actually some extra paint lying around leftover from what they paint the prison walls with.

- [Automated Voice] Press one.

To refuse this free call, press two.

(cellphone beeps) To alert.

Thank you for using.

- [Gabriel] For many years, it was just letter writing.

I was really anxious about our first few phone calls.

I was like, "I don't know what I'll say."

- [Automated Voice] You may start the conversation now.

- Hey, Jamie.

- Okay.

- [Gabriel] You know, Jamie loves to, like, tell stories and talk, so it's great 'cause usually I can just listen.

(gentle music) This one is the first portrait she ever did of me from a picture 10 years ago.

"Hope you like your portrait.

Love, Jamie."

So it's watercolor, but there's, she found little sparrow feathers in the yard and there's little feathers.

Had this one on my wall too for a while.

The little peeking out and the fingers are so detailed.

Pretty early, on a goal emerged.

It was her idea.

She wanted to build the largest collection of queer art in the world.

You know, it sounds fantastical, which, like, I love.

That's her art too, you know?

It's surreal.

It's fantastical.

So we're doing it.

She's creates work and mails it to me.

You know, now I have things, like, archived and cataloged and on a website.

These pieces are where she really talks about, you know, experiences on the inside, and I love it, the radio saying, "This is NPR."

You know, she's always listening to NPR.

This was about time she had a disciplinary action for her hair.

"A prison guard filed a disciplinary report against me for what they are calling an extreme hairstyle and I want people to know what's going on here with girls like us."

Oh, and this was just a little drawing she sent as a letter, but, you know, she's kind of gotten to know a few of my friends over the years and she wrote little notes.

This was, she was in solitary confinement.

(gentle music) She was experiencing, like, harassment and violence and really the only option is you request safekeeping for someone, and for trans people, sometimes that means solitary confinement.

(gentle music continues) - [Automated Voice] You may start the conversation now.

- [Gabriel] Mm.

(gentle music) (gentle music continues) (birds chirping) - [Gabriel] Sometimes it is difficult to explain to people what Jamie means to me.

You know, I met her in my early 20s and those were some difficult years for me.

My gender presentation at the time, on a daily basis, I'd get some sort of harassment, you know, comments or I'd get, like, harassed in bathrooms and sometimes I wouldn't wanna leave my apartment.

But over the years, like, she's been one of like the few constants in my life.

(bright music) Us both being queer and trans and communicating through letters for so long, I think we were able to build up an intimacy that I don't have with some people that I know in person.

And she's like almost twice my age.

Like, it felt like this adult figure in my life that I could talk to and get advice from.

Or we could just talk about art.

(bright music continues) "My dearest Gabriel, hi beautiful.

How are you doing?

At the moment, I have half a dozen art projects going and I can't wait to get them done so I can get them in the mail to you.

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.

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's 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.

It is getting late and your old auntie needs her beauty sleep.

So I'll close here for now.

Please take care and be safe and I'll do the same.

I love you with all my heart.

Always and forever, your Aunt Jamie."

(bright music continues) (traffic roaring) - [Daniel] Dear Jamie, I just came across your website recently.

I own a gallery in Manhattan and I'm eager to hear about you and your work.

What I see on your website is beautiful and heartfelt and strong.

I really hope to hear from you soon.

Sincerely, Daniel Cooney.

- [Daniel] "Dear Mr. Cooney, it is a joy to hear from you again.

I have been queer and trans all of my life.

Though there were periods in my life when I struggled with my own acceptance of being trans, I finally came to love who and what I am.

About my conviction and sentence: Texas laws are very harsh for robbery.

I was addicted to opiates and started committing robberies to support my drug habit.

Like yourself, I was in a very dark place.

I was out of control and disgusted with my behavior, but I couldn't stop.

It's a wonderful joy to learn of your sobriety.

Welcome to the light, and thank you for sharing.

I have no doubt that you will create a beautiful and meaningful exhibition.

Love, Jamie."

(hammer banging) (gentle music) (gentle music continues) (gentle music continues) (gentle music continues) - Hi!

- My sister.

- Oh!

(visitors chattering) - This is Jamie Diaz.

She's a transgender woman who is in prison in Texas.

- The shadows here.

I don't know, I just really, it's so striking.

(visitors chattering) (gentle music continues) - [Automated Voice] You may start the conversation now.

We're all here in the gallery.

- [Gabriel] Yeah, everything's hanging up.

It's, like, two rooms.

- It's full rooms.

All the art that you made, it's all framed and it's lit.

It's professionally lit.

- We absolutely will.

I'll make sure I'm taking pictures all night.

- I love the extras so much.

They're wonderful.

(gentle music continues) - (chuckles) I don't why that makes me laugh.

(gentle music continues) - [Gabriel] Thanks, Jamie.

(visitors applause) (birds chirping) (gentle music) (gentle music continues) (gentle music continues) (gentle music continues) (gentle music continues) (gentle music continues) (gentle music continues) (bright music) (bright music continues)