The Legend of Sasha Colby

Photo-Illustration: Vulture; Photos: Getty

When Sasha Colby introduced herself to the world as part of her RuPaul’s Drag Race season-15 “Meet the Queens” video, it was as “your favorite drag queen’s favorite drag queen.” It may sound like bravado, but it’s also accurate: All season long, as past contestants paraded through the official Drag Race recap series, The Pit Stop, nearly each one took the opportunity to name Sasha, the 2012 Miss Continental winner with two decades of drag performances to her name, as their top pick to triumph this season. Even as #TeamAnetra topped the fan vote, there remained a sense of inevitability around Colby’s Drag Race victory — she’s a legend, and she has killed this season, so shouldn’t she win?

“If Sasha wins, that would be correct,” says Kylie Sonique Love, who competed in the second season of Drag Race in 2010 and went on to win All Stars season six in 2021. “She’s so much cooler than half the girls that go on Drag Race. People don’t understand what they just witnessed when they watch her perform.”

What is clear: Audiences tuning in to season 15 aren’t just witnessing a queen’s season-long domination — Colby has won four challenges and avoided the bottom entirely, earning her the best track record of the final four queens — they’re observing a kind of history being made. Despite the illustrious, lengthy record of trans women working in the drag industry, an openly trans woman competitor has yet to win Drag Race’s flagship series in the U.S. Colby would be the first.

“As corny as it sounds, representation matters,” says Jiggly Caliente, a trans competitor on Drag Race season four and All Stars season six who’s rooting for Colby now. “I never saw somebody like me when I was growing up that was revered or considered to be super-amazing, even in the gay world.”

Representation has been a thorny issue for Drag Race. For years, the contestant pool was largely made up of cis gay men performing in drag as women. “There were trans women who were putting their transitions on hold and purposely not taking hormones leading up to the show,” says Gia Gunn, who first appeared on the sixth season of Drag Race. “Instead of being totally expressive and saying, ‘I’m a woman, and I do drag.’”

Drag Race production company World of Wonder never officially prohibited trans performers from competing, but in 2018, RuPaul made the implicit explicit, telling The Guardian he would “probably not” let a trans woman on the show, saying, “You can identify as a woman and say you’re transitioning, but it changes once you start changing your body.”

“Ru was just doing what Ru did; he is a boy who transforms into a girl. That was his idea and the whole pitch behind the show,” says Laganja Estranja, who competed on Drag Race season six and came out as trans in 2021. “I mean, you have to remember this started over a decade ago, and I don’t think people were ready to see trans individuals on TV. They weren’t really ready to see drag queens on TV.”

Nonetheless, RuPaul’s statement led to a massive fan outcry and “a very big breaking point,” says Gunn. A number of Drag Race luminaries quickly and fiercely reacted to that Guardian story — and to RuPaul’s subsequent double down — leading the host to walk back all of his comments just hours later. Gunn, who had at that point transitioned, was tapped to return to Drag Race All Stars 4 in late 2018, and since then, a number of openly trans contestants have appeared on Drag Race in the states as well as on its many global iterations.

That doesn’t mean trans performers weren’t a part of the show’s history up to that point. Love came out as transgender during Drag Race’s season-two reunion, making her the reality show’s first trans competitor — and the first person to come out as transgender on any reality-TV show.

“When I came out as trans in 2010, there were no trans people on TV at all, really. You’d see one every now and then, but they were putting them in a body bag or making fun of them,” says Love, who became friends with Colby when the latter moved to Los Angeles following her Miss Continental victory and joined the few trans women working the city’s drag bars. “I had to tell myself that I needed to be the person that I wanted to see on TV.”

Three years later, Monica Beverly Hillz became the first competitor to come out during the filming of the show, before she was eliminated in the third episode of the fifth season. In the ninth season, Peppermint became the first competitor to come out before competing on Drag Race, ultimately finishing as her season’s runner-up in 2017. Then Willow Pill, who came out between filming the 14th season and its premiere in 2022, became the first trans femme to snatch the crown.

Caliente came out as trans in 2016, after Hillz’s season and before Peppermint’s. Caliente says she was early on in her transition when she competed and was dressing as a woman but not regularly taking hormones. She decided to keep her identity to herself, in part to fend off criticism. “My biggest fear was, Will I be considered to be woman enough?” Caliente explains. “It’s one thing when people are trying to tear into your drag persona, because that’s something you created, but when they’re trying to tell you who you are as a person, that’s a different ball game.”

“Now, the girls have it — I don’t want to say easy, but they’re a little bit more protected,” Caliente says. “That’s predominantly thanks to Candis Cayne on Dirty Sexy Money or Laverne Cox or Pose. Even the girls on Drag Race who were courageous enough to tell people who they truly are. Those are the little waves that make a bigger wave for the future.”

Drag Race has indeed grown and diversified since Caliente’s time on the show, now boasting not just trans women among its roster of contestants but also a trans man, a cis straight man, and an AFAB woman, Victoria Scone, in the U.K. The show has also hosted a number of trans judges, including Cayne, Pose scribe Our Lady J, and Ts Madison, who has been a regular on the panel in recent years.

Still, Gunn confesses that the majority of the American population lacks a nuanced sense of the relationship between trans women and drag: “Even now, as we’re seeing in the media, trans people and drag queens are being all shoved into one category and all being treated the same, which is fine when it comes to a drag show but not when it comes to our rights and our livelihood.”

Estranja realizes that Drag Race’s continuing rise in popularity (the season-15 premiere was the highest-rated in six years) has coincided with an increase in threatening anti-trans and anti-drag legislation. “I think that the more successful we get, the more visible we become, the more the people who are against our lifestyle and choices want to try to drown that out,” she says. “I really believe that it always gets worse before it gets better, and that’s kind of the time that we’re in right now because it is getting worse and it is becoming increasingly dangerous. But as that happens, we are also creating more space and clearing out more landscape for us to ultimately win.”

In this way, Colby’s domination this season has been, simply put, “a symbol of hope and of somebody who made it through the darkness,” Caliente concludes, “and out of being told, ‘You’re not good, you’re not right. You’re wrong for who you are.’”

Love agrees. “Sasha winning would mean so much not just for trans people but for anyone who ever believed in themselves even though a lot of the world was saying that they’re wrong or they’re not doing the right thing,” she says. “Ultimately, too, I think it’s going to inspire a lot of trans people to maybe start doing drag or to put in their tape for the next season. I know so many fabulous trans queens, and if they get an opportunity to compete on Drag Race, it’s going to create a whole other level of excellence.”