Let’s Talk About Caitlyn Jenner: Part 1 of 2

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Every disenfranchised group has to deal with its Fifth Columnists. Black folks have Stacey Dash. The upshot is that Stacey is far from being the most well known black woman in entertainment, journalism or politics among black or white people. Conservative voices among the marginalized are rarely the most prominent voices. More people know Margaret Cho than Michelle Malkin. More people know Aziz Ansari than Dinesh D’Souza. I’m also a firm believer that minorities should not be expected to be monolithic in opinion. Expecting anyone to be in lockstep with other people of their race, gender, or sexual orientation is its own form of discrimination.

And that brings us to the very special case of Caitlyn Jenner. Caitlyn Jenner is without a doubt the most famous out transgender person alive. Sure, Laverne Cox’s picture was on the cover of Time Magazine in 2014. Caitlyn Jenner’s picture was on the box of Wheaties on my breakfast table in 1978. When she announced her gender transition, there was a Vanity Fair cover story, a prime time network special and a reality TV show waiting for her.

Caitlyn Jenner could use her unprecedented platform to champion the cause of her transgender sistren and brethren. Or she could have taken a do-no-harm approach. However, with public statements like “If you look like a man in a dress, it makes people uncomfortable,” she has endorsed the kind of transphobia that she as an insanely rich, older white woman can largely shield herself from in ways that school age or working trans women, particularly trans women of color, simply cannot.

As you can see, I have a lot of feels about Caitlyn Jenner, but as a heterosexual, cisgender man, standing on a platform afforded to me not just by my own work, but by the work of all the founders, leaders and volunteers here at Sex Positive St. Louis, I thought the move would be to make space for the voices of trans women in our community. This conversation took place in mid February, not long before Jenner endorsed Ted Cruz for president.

Dramatist Personae:

Jaimie Hileman – Board President of Metro Trans Umbrella Group of Greater St. Louis

Joss Barton – Writer and Artist

Ruby Threadgill – Radio Personality, founder of Generation Next

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SEX+STL: If you could ask Caitlyn Jenner one question, what would it be?

Joss Barton: “Is it a wig or a weave, girl?” [Laughter]

Jaimie Hileman: She has been anointed as a leader, if not the leader, of the trans community, and certainly of the trans feminine community, by the media. I think that’s a very safe assumption. So accordingly, I would ask her, as such, what does she think that she has done for trans women, and does she think she has been successful at it?

Ruby Threadgill: I would say, “Do you want that position? Do you want to be the face of the trans community? Is that too much pressure? Is this a role you actively want to take?”

Joss: When I came out to my best friend growing up — I’ve known this girl since we were literally in diapers — and when I told her “I’m trans, I prefer the name Joss now,” the first thing she said, “The only thing I have to relate it to is Caitlyn Jenner.” She’s from a small town that I grew up from, and to her that was her only experience with trans identity. I did have a benefit because it helped her understand a little bit about what I had been going through throughout my entire life, and she was very positive, and she’s like, “I accept you. It’s going to take me some time to get used to the name and the pronouns, but I love you and I support you.” So [Caitlyn Jenner’s] presence does have that effect. I’m from a town of less than a thousand people, so for that to trickle down to one of my childhood friends, yeah, that is a positive.

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SEX+STL: So Caitlyn Jenner once said, “If you look like a man in a dress, it makes people uncomfortable.”  Thoughts?

Jaimie: This is one of the comments from her that made me, if not stop defending her, at least become extremely precise in my wording. Caitlyn Jenner does not know much about trans people. She doesn’t know very many trans people. Her transition is different from 99.999999% of other trans women’s. Everyone’s journey is different, everyone’s journey is unique, but hers in in a category that is completely stand-alone.  So a lot of the shared experiences that we have, and how we’re judged according to society’s toxic beauty ideals, and how women and the feminine are punished and our society, how the rest of us in the trenches have to deal with that, is not [her] problem. Ninety million dollars insulates you from a lot of crap. So for her to say that is not only damaging to trans people and to trans women, but just to women, because it upholds the societally dictated ideal of what being female is.  And no woman, trans or cis, should be pilloried according to an artificial set of standards that, quite frankly, none of them got to vote for.


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SEX+STL: If you could write your fantasy version of a Caitlyn Jenner speech or a Caitlyn Jenner moment, what would it look and sound like?

Ruby: To come from that point of privilege and to reach out to everyone in the trans community… I would like for her to acknowledge her own privilege and say, “I realize that not everybody can afford their medications, and I realize I had all this right out the gate, and I came out the gate running while everybody else is crawling, and crying, and in pain, if they get there at all! If they get through the barrier of therapy — if they can afford therapy!”

For her to acknowledge her own privilege and say, “I may not be able to relate with you on that level, but I empathize with you and I’m here for you.” But I’ve seen no such thing from Caitlyn Jenner.

Jaimie: …acknowledge her own privilege in terms of her class privilege and how that has isolated her from a lot of the problems that ordinary trans women have to face. Even middle class trans women with careers, with some life equity, with insurance, still get their turn in the barrel, more often than not. Much less the fact that the majority of trans women are not middle class. The unemployment rate in our nation is 4.9%. For trans people: 18%. For trans women it’s 28%. For trans women of color it’s 60%. So, I feel like we need to hear her acknowledge that, and we need her to explain why she says she’s a Republican, and I really mean that. Not because I’m pillorying Republicans in general when I say that, but this is a political party and part of its platform regarding trans people is, one: no legal recognition of trans identifies, and two: this from the party platform, “no creation of classes of special protection,” which is code-speak for denying under the 1964 Civil Right Act, Titles 7 and 9, and the 14th Amendment, denying inclusion of gender identity as well as sexual orientation as equally protected as all the other protected classes and statuses in federal civil rights legislation. That is part of that party’s platform. So, as trans woman saying that she’s a Republican, she says I’m going to vote for the party that wants to make sure I am less than and I do not have the same human rights or civil rights as my fellow Americans. I think that’s problematic. And as someone who can really act in the political sphere with a 90 million dollar fortune, I think she owes us an answer there.   

So that’s class privilege and the politics associated with that class privilege, and white privilege. I really want to see her get to know some trans women of color and what they have to go through.  Because I assure you, she does not know jack. I would like to see her spend some time in the trenches, I’m not asking her to write big checks, for trans activist groups and to support shelters and HIV screening and prevention clinics, that would all be very nice. I’d like to see her volunteer her time in the community and use the power that she has. Maybe she hasn’t, and she says she hasn’t, wanted to be the queen, the empress, of all trans people, but she is! Just by the nature of her fame with her previous male presented identity and who she is now, and how she came out, she has that power. I want to see her use it for good. She can’t do that until she confronts her own privilege: class, race and the political connotations associated with that. And I want her to read a book on feminism.  

Joss: The only thing that I would add, if I could have her really get raw with people, would be to admit the complete fantasy that is that reality show that she’s in. It’s all constructed, it’s all fake, it’s Hollywood! And she’s been a part of Hollywood for a long time and as Ruby and Jaimie have said, she’s been insulated because of her wealth and her privilege, but I would love for her to just be like, “This is all smoke and mirrors. My gender identity is real, but what you’re seeing is all smoke and mirrors, it’s all been thought up in a production room with writers and producers.” I would like for her just to admit that. I don’t know if she would ever do that. I think if she were honest about that, it would assist in regaining a lot of the trust she’s lost in the last year with trans people and trans activists and trans communities, with her comments. Her political affiliation, which Jaimie is completely right about, is one hundred percent against trans dignity and humanity. How can you expect an entire culture and nation to embrace your gender when you are actively supporting and voting for a political party that wants to see us erased from the face of the planet?

So, if she she would just break that fourth wall and say, “This is all fake, this has all been created for your consumption,” then I would have a lot of respect for her if she did that.

Ruby: Having her go through, like, an Undercover Boss thing, where she would have to go as an average poor or middle class trans woman and have to change her whole wardrobe with no budget.

Joss: [Laughs] Yeah, take her ass to Dots!

Ruby: My wardrobe, the majority of it were gifts, or it came from a thrift store. I can’t afford to buy an entire wardrobe, and take care of my son, and pay for my hormones. Have her walk a mile in our shoes.

Joss: That’s brilliant.

Jaimie: I would like to see her do that reality show.   

In part two, we discuss I Am Cait, and Caitlyn Jenner and Kate Bornstein visiting St. Louis for the dedication of the Transgender Memorial Garden. 



David Wraith is a co-founder of SEX+STL, the HNIC of Planet Wraith, and a self-described “street-walking cheetah with a heart full of napalm.” 


  1. when I told her “I’m trans, I prefer the name Joss now,” the first thing she said, “The only thing I have to relate it to is Caitlyn Jenner.”

    My partner, when they told their mother about their gender, heard the same thing. The positive side is that she had anyone at all she could relate it to. The negative side, of course, is that person’s life is nothing like ours.

  2. I love this piece. Caitlin is so problematic for us. I understand that she had a struggle, she didn’t transition into very late in life, but as you all said, she is blind to our struggles.

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