Trans Talk

Trans Talk: Is Don Draper an Honorary Trans Man?

· Updated on August 5, 2022

Trans Talk is a series of conversations, each bringing a different trans person to the table to have short discussions about a topic they feel strongly about identifying as trans. 

Our guest this month is film critic and researcher Caden Mark Gardner, whose work you can find at Criterion, Reverse Shot, MUBI, and more. Caden, alongside writer Willow Catelyn Maclay, has been working on a series of conversations about transness in cinema entitled Body Talk for years now, and the duo is working on a book on the subject titled Corpses, Fools & Monsters: An Examination of Transgender Cinema

One point in their latest edition of Body Talk, on Torrey Peters’ novel Detransition, Baby, has led us straight here: when Caden says he’s not joking about accepting “Don Draper from Mad Men as an honorary trans man.”

Juan: Okay, so, as long as I’ve known you, I’ve seen you posting memes and casually referencing trans Don Draper and I have wanted to do a deep dive into it, so here’s our chance. Obviously you’re not the only person to have this take, as the delightful (and fake) Niche interview with Jon Hamm about Don being trans shows us (among some other examples online,) but I’ve always been interested in your insights on it. Before we dive into the series and character itself, how’d you come to making this bold statement and what does Don mean to you?

Caden: I remember when these connections hit me while the show was still on and really was not finding anything beyond maybe one blogger (who I assume is also trans) who contrasted real-life trans disclosure and living stealth with how Don managed (and mismanaged) dealing with his past on the show. That piece was dated in 2010, at the height of the show being considered in the lineage of The Sopranos, Deadwood, and The Wire as the next great prestige television phenomenon. But that piece was an outlier. I was really plugged into TV Twitter at that time (and had been following Emily VanDerWerff before she came out and before I was out.) Gender—let alone transness and queerness—were not really topics discussed in deep ways by the TV-recapping industrial complex. And most queer outlets at the time really only cared for the things that exclusively to them. Their Mad Men pieces were more focused on Sal Romano or Joan’s tragic lesbian roommate briefly appearing, and then they would just go back to The L Word, RuPaul’s Drag Race, or Mitchell and Cameron’s hijinks on Modern Family. And it made sense. Since the show’s inception, Don had been presented as the suave catch for women to love and for men to be: a white cis heterosexual icon. You could not get more traditionally heteronormative than him. Don was also placed among “Difficult Men” characters and narratives (and their male showrunners) that emerged from TV of that era where flaws (infidelity, misogyny, possessiveness, alcoholism) were part of the fascination. But to me, Don is significantly different from others like Tony Soprano or Walter White in that he often feels in a constant psychological loop of existential crisis and angst that is removed from violence or violent crime that are synonymous with those other characters. Don’s whole issue is a reconciliation of the past with his present that to me is a major fulcrum for many of us who are trans and go through the many changes, transitions, disclosures, and non-disclosures in order to become ourselves. 

Gender—let alone transness and queerness—were not really topics discussed in deep ways by the TV-recapping industrial complex.

I started watching Mad Men around Season 2 when I was just starting college completely closeted and at a school that, at the time, had a really stifling gender binary. I really got drawn into the fact that Don’s ‘secret’ in being born Dick Whitman, a bastard child of a dead sex worker born into poverty in a very unloved, abusive environment, was still a thing only a handful of people on the show knew and had varying reactions to it. The question of “Who is Don Draper?” was teased in the first season and I think many people had found the revelation that this was a man who switched dog tags with a superior officer in battle to be so melodramatic or incorrectly viewed it as a Chekhov’s gun moment that would end with Don being taken down for this secret. But that moment clearly is a life-saving chance for Don to get a new lease on life and reinvent himself, even as withholding this part of his life proved to be something that continually haunted Don throughout the series, which peeled back even more of his past that showed more unsavory trauma that made him less aspirational and more of damaged goods. 

By the time the show ended, I knew for sure who I was as a trans man, and felt kinship with Don as a character. I saw myself in him, albeit one where I connected more to the screwed-up nature of his backstory, particularly the alcoholism, which by the time the show ended I had hit my peak with. I finally wrote about connecting to Don as a “role model” when I was beginning my sobriety journey and also starting hormones. I would say even looking back at my deeply earnest outlook at that low point in my life that I still back my general take that Don Draper as a character has a story that does run extremely parallel to a certain trans narrative of the not-so-distant past. This goes beyond just a personal connection, although I still see myself in Don in re-watching the series since it last aired. 

To me, Don is different from Tony Soprano or Walter White in that he often feels in a constant psychological loop of existential crisis and angst that is removed from violence.

Juan: I’ve always found it somewhat frustrating when people lumped Don into the loose category of contemporary television antiheroes. “Damaged goods” is kind of the perfect summation for him; he’s trying his damnedest and stumbling along the way because of all the baggage he’s got. Something that stuck out to me in your piece on Don as a role model was the fact that you emphasized how almost mundane coming out can be: you came out to your mother in the parking lot of a Chipotle. I came out as queer to my mother when getting picked up from a friend’s house after she saw my Myspace (oh god I’m dating myself) and I still kind of side-step the conversation of what nonbinary is. It’s interesting how, when looking back at the show, you could argue that his moments of major vulnerability, of breaking down and revealing whatever precious amount of history and trauma he’s willing to share at that moment, aren’t necessarily, like, life-changing. Obviously, Matthew Weiner knows melodrama well and can sort of make these seemingly minor moments into something major, but it’s still something like a bad day at the office, a phone call, a pitch, etc. 

Beyond personal connection and coming out, you wrote that “his character backstory and trajectory is basically the story of every stealth trans man and trans woman in the twentieth century” in your piece. So, now, hit me with all the Hobo Code of Transness that Mad Men has to give us.

Caden: There are a few things I am going to bring up here as far as both historical and fictional parallels to Don that to me connect to why I and a few others connect him to trans narratives. My co-author Willow Maclay and I often speak about Don Draper together in terms of being ‘stealth’ or rather, that he passes undetected by society at large. He grew up with a different name, a different life, a different part of the country that was far from John Cheever’s Ossining suburbs, let alone Madison Avenue, a past tied to trauma and shrouded in secrecy that he takes great pains to never talk about—even with loved ones—or have re-enter his life in any way with very few exceptions. There are many trans stories with similar makeup and context both real and in fiction. I call them the Anna Madrigal generation of trans people. To me Don has more similarities to Anna Madrigal than Walter White. She was a character in the Tales of the City book series and the television show as portrayed by Olympia Dukakis (and later Jen Richards’ when the recent reboot went back in time to cover Anna’s origins story.) I know for trans people and queer people of a certain age that Anna Madrigal really struck a chord of somebody who did the queer migration of moving out of her hometown (she too raised in a brothel house) to San Francisco and resetting her whole life as a pot-loving landlady and a maternal figure to women and queer people. There is a point where she does disclose her life as a trans woman and it is not this salacious shock but colors everything we know about the character, and Maupin really does embrace exploring her story further in books and shows. But back to why this character matters: this is the reality for many trans people who preferred to uproot and fly under the radar with their situation and living stealth, toeing a really fine line of who to disclose to or ever at all. There are so many stories of somebody’s parents or spouse dying only to find out they were trans after the fact. 

This brings us back to another real trans person who I also saw elements of with Don Draper and that is the jazz musician Billy Tipton, whose story re-entered a lot of trans discourse with the documentary No Ordinary Man: The Life and Death of Billy Tipton that recently came out. It is widely speculated that Billy’s choice to withdraw from public and a potentially lucrative jazz career is based on the fear of his past being coming to light, a tragedy that ultimately does happen when his death and surviving members of family are scrutinized in abhorrent, transphobic ways for ‘not knowing the truth’ about Tipton’s ‘fraud’ life. But that tension of knowing the risks and assessing what you cannot reveal about yourself is a very trans experience in trying to preemptively combat being outed, even if it means capping your own potential out of safety. I made a personal choice in not getting into published film criticism when I was not yet legally under this name, and I did that to protect myself from having to disclose, and I still have mixed feelings about that decision.  In the Mad Men Season 4 episode “Hands and Knees,” there’s this plot thread of where Don Draper has a panic attack involving the fact that the United States Department of Defense is doing a security clearance on all Sterling Cooper Draper Pryce employees due to a potential contract with North American Aviation. His fear of his past coming to light not only has him disclose his past life as Dick Whitman to then-girlfriend Dr. Faye Miller during that panic attack, but he also kills the account. Pete Campbell, the man who previously outed Don to Bert Cooper, willingly takes the fall at that agency. They both know the risk was potentially too great for an agency that at that point in the show was teetering on the edge to have that come out.

There are so many stories of somebody’s parents or spouse dying only to find out they were trans after the fact. 

There are moments like that on the show where Don, while impulsive and careless a lot of the time, has formulated and adhered his own set of rules at work for self-preservation, albeit that gets murkier when he brings his personal life into his work. Every now and then there are things that catch him by surprise, like when a former Army buddy reappears by chance on a train ride and refers to him as Dick Whitman. Don stays silent but the shame of being ‘clocked’ is there. At work, Don avoided getting kicked out of the Time & Life building for his occasionally destructive behavior because of the Don Draper he brings into the board room, to paraphrase Bert Cooper, not batting an eye when Pete Campbell first tries to out Don. Essentially, be this idealized avatar of postwar masculinity that makes clients feel good about their product’s ad potential, but never show Dick Whitman. Oh, but it comes out and how!  The Hershey pitch in the Season 6 finale (“In Care Of”) to me is a coming out moment, a disclosure. The shakes, the face collapsing in his hands, the flying from the seat of his pants approach to finally speak his truth. Nobody in that room knows what to do with it or react. Out of everything he has done working with these people, showing this side and to one of the biggest American brands in the room no less, this was a bridge too far and something that places him on leave. He does not say everything about how he goes from living in a brothel to present, but it is just enough to make everyone feel uncomfortable and question who has been working for them this whole time. Ultimately, we see how being stealth does drain somebody and make them crack in a moment of darkness that also at the same time can be this poignant release from a sense of pain and shame. “Both Sides Now” by Judy Collins closes that episode and it really is a beautiful coda to underscore that Dick Whitman and Don Draper are not these altering egos but part of one person who, while brilliant, is dark, brooding, fears abandonment, abusive, traumatized, and has very few healthy relationships with women.

The Hershey pitch in the Season 6 finale (“In Care Of”) to me is a coming out moment, a disclosure.

Juan: I love that you bring up Billy Tipton and No Ordinary Man because that was one of the first things that came to mind, as did the recent docuseries The Lady and the Dale. It’s refreshing to see how critical both documentaries are of individuals who try to rewrite history simply because the person isn’t alive to defend themselves or to explain their journey the way they had it. When something doesn’t conform into an easy narrative, people lean into transphobia. To tie it back to “difficult” characters though, something Susan Stryker says in Lady has stuck with me for months: “There’s this hunger to see a life that you can aspire to, to emulate. Liz Carmichael is not an easy person for us to think of as a role model, but at a deeper level, there’s something that’s really compelling about Liz’s story.” 

The reality of a lot of trans history, from what I’ve read and seen over the years, is that things aren’t as neat and simple as many would like to frame them. Folks like Tipton and Carmichael are sort of atypical trans role models to what a lot of folks want; one lived quietly and one lived brashly, each adapting to the circumstances around them in whatever way they could that was best for both their survival and their attempts at accomplishing their dreams. 

As I revisit shows like Mad Men and even The Sopranos, I find myself identifying more and more with these characters who are, ultimately, navigating their own forms of identity crisis. They aren’t remotely queer-coded, and queerness is often a subject of ridicule for the men that populate these shows, but that core conflict—of what one presents to the world being pit against what one navigates internally—is so essential to why I find myself drawn to them. I know we just mentioned that Don is a bit removed from someone like Tony Soprano, but I can’t help but think about just how similarly patterned their explorations of fractured identity are. Their endings and approaches to life are radically different, in part because of their histories and the eras in which they exist, but so much of their respective journeys and finding some semblance of peace with themselves (whether or not you think they truly attained any peace) is about having conversations, of being open with someone else (and, for both of these men, their revelations come from the women in their lives.) 

The reality of a lot of trans history is that things aren’t as neat and simple as many would like to frame them.

So many of these characters exist with secrets that are not intended to be malicious, they just don’t feel the need to reveal these stories unless it’s outright necessary (be it for their own mental health or for the sake of getting ahead.) To close out, I want to ask: as you’ve navigated such a wide variety of stories over time, both explicitly trans and works that you find trans coding in, do you feel like there’s a lot to be learned from characters, like Don Draper, who are far removed from what people expect to find transness in? 

Caden: Likewise, I am glad you brought up The Lady and the Dale and specifically Stryker’s commentary. I think co-directors Zackary Drucker and Nick Cammilleri also smartly confront the media circus around Liz Carmichael tying her lack of credentials and fraudulence in her work to the fact she dared to live as a woman, a “fraud” in a deeper sense. Cis people can pat themselves on the back that we have progressed from Liz Carmichael’s time, but I remember that terrible—since retracted—piece on Grantland in 2014 about “Dr. V and the ‘magical putter’’ story. Essentially, the writer outed the piece’s subject as a trans woman after already calling out her credentials and what she was putting out there in golfing. Dr. V committed suicide before that piece’s brief publication. There are cis people who still instinctually make that link that the trans people are frauds, either sick in the head or just built to lie and deceive. This transphobia is tied to cultural images of ‘trap narratives’, bathroom bill scare tactics, reveals on The Jerry Springer Show, and going back to earlier decades with the existence of “masquerade” laws where being in ‘drag’ or any gender non-conforming clothing was against the law in many parts of the United States. The newspaper headlines of those incidents can be found in any trans archive. I think there is an instinct among trans people of wanting to turn away from this kind of history because those ideas still persist now. It is difficult to reckon with how society so poorly perceives us and that this type of visibility entails so many risks in being locked away or the anxiety that it is only a matter of time for you to be clocked and what else could come from that in the form of violence: losing a job, losing a place to live, etc. I also just think that respectability politics now just don’t want us to embrace the complications of our ancestors let alone characters of fiction. 

As I revisit shows like Mad Men and even The Sopranos, I find myself identifying more and more with these characters who are navigating their own forms of identity crisis.

It is funny to think about how The Sopranos has consistently popped up in other queer and trans writing as a popular show in and out of quarantine. But I also think that is consistent with those of us who, due to lack of direct representation, found these embers and connections to shows that were not ‘meant’ for us—as if that lack of representation has ever stopped us from being viewers and consumers of visual media. Even when shows like Orange is the New Black and Transparent emerged, I found the constant presumptions that I was supposed to love these shows because they had trans people involved to be off-putting. I also just felt like those shows often were doing some Trans 101 introductions of many of those characters. Also, it’s not like these shows completely avoided queerness or acknowledged there to be potential queer readings, especially when so much about Mad Men is about assimilation and passing in polite society. Take the character of Bob Benson. Bob to me is the sort of olive branch the show made in acknowledging the queer coded parallels of its very white, very straight lead. Bob was Don’s double, a people-pleasing, male Holly Golightly social climber with very hazy origins and a forged past. Bob was not going to be a gay liberation hero but somebody who was deeply calculating, cautious about who he made friends with and how he presented himself in public. He had the, “Best Little Boy in the World” syndrome as Tom and Lorenzo beautifully put it in addressing the character in the “Mad Style” column when the show was on the air

I have always seen Don as somebody who is searching. Trans people are not running, they are more likely searching as well.

Bob’s future as a Detroit car executive beyond the show suggests a very unhappy life in living in the closet. Same for Sal Romano, although he potentially plays with fire as a guy who lives on the down-low at gay bars. They cannot reconcile, although it is often due to the ways in which society stifles their existence to live out more freely. Don’s issues are more cumbersome. Even without the name change, or he had just gone under any different name, there would still be that past that he had to physically and mentally get away from. He tries to avoid thinking about it, but it loomed like a spectre for seasons, to the point of exasperating many viewers. 

As far as what can be learned from the character, I think there have been some bad faith readings of the show right down to the interpretation of the famous Coke ad in the finale. People read it as a sneer, that Don’s last act on the show is co-opting the hippie movement, because he’s an empty vessel and blah, blah, blah. I think there was a contingent of viewers who expected—maybe even wanted—Don to be caught as a fraud or die with the revelation of his ‘secret’ being revealed to everyone. I think people see a man constantly on the road and feel like he is running from something and want that literalized. But I have always seen Don as somebody who is searching. Trans people are not running, they are more likely searching as well. Don often does feel in suspension and alien to the rest of the world that both benefits him in having a very unique gift, makes him alluring as the solitary figure, and also isolates him from having a connection, a community to go back home to be with. That has always been the melancholy of his character that goes back to season 1’s “The Wheel” where he has these photos of familial bliss that he even uses in a pitch to Kodak and he imagines coming home in this picture-perfect Thanksgiving in Ossining that is not to be, and he just feels deeply removed. He either shirks the opportunity to do these things or his lack of engagement is the utter lack of familiarity with it due to his upbringing. I read the finale moment of the show with the Coke ad as deeply bittersweet. Here is his strongest form of expression, his great talent, wielded into what he wishes he could express and connect with through what he does best. It’s noteworthy that the ad itself is a fantasy of the communal, versus his archetypal, singular focus of earlier ads he had done on the show. It is a far cry from Lucky Strike. I took it as a potential step forward from him in being able to be more at peace with what he can and cannot be. I think his journey is about the meditation of identity of past and present that I think is an absolutely essential component for those of us who have often had to hide ourselves in some way from the rest of the world. And yes, it always helped that he was embodied by Jon Hamm’s chiseled square-jaw exterior, but Don Draper is my trans masc icon and I do not even hesitate to define him as such. ♦

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