Aryana Noroozi
Devlin Winston, Community Health Worker at St. John’s Community Health’s Transgender Health Program, opened T-Boy Tuesdays’ June 9 Paint & Drag event with a presentation on trans men in history, tracing documented evidence of trans and gender-nonconforming people back to 1528.
T-Boy Tuesdays, a recurring gathering co-presented by the Transgender Health & Wellness Center and St. John’s Community Health’s Transgender Health Program, hosted its Paint & Drag edition from this month as part of Pride Month celebrations. The evening wove together art, performance, and a pointed reminder: trans people have always been here.
The night began with a networking and gaming hour, followed by the paint and drag session, during which attendees could paint the live drag models. A karaoke and games intermission bridged the creative session into a presentation on Trans Men Through History.
As the painters placed finishing touches on their canvases, Devlin Winston walked attendees through documented evidence of trans and gender-nonconforming individuals across centuries, ranging from a Spanish explorer’s 1528 account of gender diversity among Indigenous people in Florida, to anti-cross-dressing ordinances passed in Missouri as early as 1843, to the trans men who lived, organized, and died during the AIDS epidemic of the 1980s.
Among the figures highlighted was Morelo, described as a Mexican revolutionary who lived openly as a man for 70 years and is considered one of the earliest Latin American trans men officially recognized by the state. The presentation also featured Wilmer Broadnax, a gifted gospel singer active from the early 20th century through 1992; Michael Dillon, a British physician who is among the earliest documented individuals to undergo a full female-to-male medical transition including hormone therapy; and Reed Erickson, who established the Erickson Educational Foundation to fund trans research and organizations.
The 1980s emerged as a particularly significant chapter. Winston cited the 1986 founding of Female-to-Male (FTM) San Francisco, a support group that grew into FTM International and now stands as the longest-running female-to-male organization serving members across 18 countries. The decade also brought a formal medical pathway for trans individuals to access gender-affirming care, opening doors for a generation navigating both transition and, for many, the AIDS epidemic simultaneously.
That intersection of trans identity and the AIDS crisis was among the revelations Winston said affected him most deeply while researching for the event.
“They were walking around stealth, keeping their lives — regardless, they were here,” he said.
The decision to center trans history wasn’t incidental. In a conversation before the presentation, Winston spoke directly to the current political moment, including the erosion of gender-affirming healthcare access for many in the community.
“A lot of people are losing their medical insurance and not being able to proceed on,” he said. “So kind of touching back in history – to let people know that they’ve always put that pressure on us, and we’ve always been able to get through…and keep going strong.”
The through-line of the presentation was resistance not as a new posture, but as an inherited one. Winston cited anti-cross-dressing laws, Christian missionaries pressuring Indigenous tribes to conform to binary dress codes, and medical institutions slow to recognize trans identities. Each example placed today’s legislative battles inside a longer arc, one that trans communities have navigated and survived before.
“We didn’t just pop up four, six years ago because now the other party wants to start talking about us in such great detail,” Winston said. “No, we’ve been here for a long time. It goes from Indigenous tribes, to first settlers, to the Black community, to the Latino community. The history is there.”
What made the evening at Back to the Grind distinctive was its refusal to separate the joyful from the serious. With painting and performances, the Transgender Health & Wellness Center and St. John’s Community Health created a space where community care, artistic expression, and political consciousness coexisted within the same three hours.
“This isn’t the first time we’re going through this,” Winston said. “This isn’t going to probably be the last. But we sure as hell keep fighting, and we’re going to keep going.”