11 Victorious Hillary Clinton Illustrations That Could Have Been

Here, a collection of unpublished cartoons commissioned by The New Yorker, GQ, and more.
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A lot died when Donald Trump won the presidency—facts, optimism, our will to exercise. Not least of which were some incredible Hillary Clinton victory cartoons that never saw the light of day. The following illustrations were commissioned by magazines ranging from The New Yorker to our very own GQ.com to the Clinton campaign itself. They were made with the historic first female president of the United States in mind, and would have run in print and online the morning after the election. Instead they were left unpublished, until now. We talked with ten artists about what these graveyard Hillary portraits and cartoons mean to them.


Cun Shi
(Image above, commissioned by GQ.com)

My initial idea was to incorporate aesthetic elements from vintage election posters. I did a lot of visual research and studied photos taken from different angles in order to get a better sense of her features and expression. Sometimes I like to draw a face several times to make sure it feels right, with each attempt getting closer than before. For this piece, I got it right on the third try.

What were you thinking as you made the illustration?
Can't remember...but the last thing that was going through my mind at the time was Hillary losing the election.

How do you feel about art in the age of Trump?
I’m honestly not sure. The times ahead are filled with uncertainty. I’ve been to countries where the top policymakers value neither culture nor art...it was very depressing, to say the least.

Who is more fun to draw, Hillary or Trump?
Probably Trump.


Julia Rothman
(Commissioned by the Hillary Clinton campaign)

Jennifer Kinon, the creative director for the Hillary campaign, called me up on the Tuesday before Election Day. She told me she wanted an illustration for after the victory, something that showed every president and then Hillary, like one of those vintage president charts. She needed it as fast as possible so she could get approval and make some product. I told her I was on it! That evening I started drawing the presidents one by one, pretty quickly, trying not to care about likeness too much, just making them recognizable. I posted it on Instagram the day before the election, and a friend texted me, “Not yet! You’ll jinx it. Wait until tomorrow.” So I took it down.

What were you thinking as you made the illustration?
I was thinking, “Wow, so many white men!”

Did you feel personally involved in her campaign?
I was pretty involved from the very beginning. Jen is an old friend, and we’ve collaborated many times before. I was thrilled when she asked if I’d like to contribute artwork to the campaign. I live-drew debates and rallies and made art for a tote bag, a poster, and T-shirt that was sold on HillaryClinton.com. My artwork was on Hillary’s buses that toured the country.

Who is more fun to draw, Hillary or Trump?
Trump is too easy to draw. He is a caricature already. I can draw Trump quickly, and it always looks like him. Hillary takes a bit more concentration. I have to draw her a few times before it starts to look like her.


Jing Wei

These were originally quick thumbnails for a more finalized piece. I was watching a few of Hillary’s past speeches for reference, and the sketches ended up being more of an immediate response. I think the unfinished quality of these drawings seems appropriate in this case.

What to you was most exciting about her potential win?
Leading up to the election, the year had been utterly dismal and at times terrifying. The most positive moments have come from people banding together and showing support in the aftermath of great tragedies. Hillary’s win would have been a sign that there could at least be some amount of progressive change, that there could be support and protection for the rights of women, LGBT, immigrants, and minorities, and that the nation wasn’t being dominated and ruled by hate. It was a matter of reassurance versus a very scary unknown.

How do you feel about art in the age of Trump?
I made zero artwork in the days following the results. I kept thinking, “Should I be drawing something? Is that enough?” And then I started seeing Post-its in the subway, art roundups in the newspaper, personal work being shared on Instagram. It kind of broke that moment of paralysis, and I was reminded of how art is just a tool like anything else. It can and needs to be used to educate, heal, empower, protest, and document, now more than ever.

Who is more fun to draw, Hillary or Trump?
Trump. It’s always more fun to draw the villain.


​Lauren Tamaki
(Commissioned by New York magazine)

I was so psyched that there was a possibility of a) a lady president and b) a chance to work on a possible cover image to celebrate this event. I wanted to capture a thoughtful, happy expression with eyes looking toward the future.

Did you feel personally involved in her campaign?
As a Canadian in the U.S. on a work visa, I actually couldn't get involved on many levels. I did a lot of political illustrations during the election (including a couple live drawings for The New York Times during the RNC and DNC), which makes me feel like I participated in some way. I followed this election very closely, and I really wish I could have voted! She isn't the perfect candidate or politician, but I agreed with her stance on reproductive rights.

Who is more fun to draw?
Honestly, Trump's exaggerated facial expressions make him easier to draw, but I wouldn't say it's fun...


Ben Schwartz
(Commissioned for NewYorker.com)

I do a topical daily cartoon for NewYorker.com, and one of the ways I keep that interesting for myself (and hopefully my audience) is by playing the news of the days against other parts of pop culture, past and present. In my naive mind, election night was going to deliver closure. It was going to be “game over” for Trump—which made me think of the classic Chappelle's Show sketch about Prince playing basketball and declaring victory with the immortal words, “game, blouses.” Swapping Hillary for Prince and “pantsuits” for “blouses” worked quite nicely, I thought, so I decided to draw it up ahead of time.

What to you was most exciting about her potential win?
This is probably the cliché answer, but I was most excited by the idea of having a woman in the White House, and the change and progress inherent in that.

How do you feel about art in the age of Trump?
At least as far as the art of political cartoons goes, I don’t think he’s the comedic boon that some people assume he is. He’s already so cartoonish and over-the-top that it can actually be pretty tough to figure out how to add a joke on top of the reality.


Hilary ​Fitzgerald Campbell
(Commissioned by Cup of Jo)

When I thought about doing a "post election" cartoon it seemed the answer was so obvious that we could all just go on with our lives--so that's exactly what I drew; people going back to business as usual, with a little pep in their step, knowing their president elect was a qualified, kick-ass lady.

What were you thinking as you made the illustration?I was excited about it! I was excited to move on; to laugh about what a crazy year it has been--and to never look back.

Did you feel personally involved in her campaign?Normally I shy away from politics. I don't enjoy discussing them (I really hate arguing), but this is the first election for me that has felt truly personal. In the beginning, I was much like the rest of the country, not taking the other side seriously--but as time went on, it became more real for me. So yes, as a woman, as a feminist, as an American, I felt personally involved. (Also my name is Hilary so ya know, solidarity)

How do you feel about art in the age of Trump?In times like these, art is more important than ever. It has to stoke the fire, to not shy away. As artists, we need to be loud and unafraid. Especially in the public eye. I've personally had moments of, is it ok to post this? Will I offend anyone, maybe close to me? And you can't think like that. You have to make the art true to you and never apologize for it.

Who is more fun to draw Hillary or Trump?Trump is so ugly (in body and in spirit), I have never drawn him and honestly, probably never will. He simply does not interest me--and I felt the whole issue with this election was the fact that we ever even gave him any attention. I'm getting off topic here! Hillary is way more fun to draw. Women in general are more fun to draw--just look at them.


David Sipress
(Commissioned for NewYorker.com)

These days I am drawing the Daily Cartoon on newyorker.com, publishing a topical/politically themed cartoon every weekday. I like to wait for an idea to hit me close to my Daily Cartoon deadline so that my cartoon will be in direct response to the most current news stories. I drew the first version of the cartoon—“Whew!”—at 6 P.M. on election night, convinced like the rest of the world that Hillary was a shoo-in. I was trying to express the enormous relief that would be felt, not just in America, but all over the world, once Trump was history. And sadly, Photoshop came in handy again at 11:30 that evening, when the totally unexpected—and, for me, frightening and tragic—reality set in. I erased “Whew!” and, almost without thinking, wrote in exactly what I was feeling at that moment, and what I assumed that people around the globe were feeling: “OMFG!” I hated making that change.

Did you feel personally involved in her campaign?
I felt deeply involved in Hillary’s campaign, in large part because my work caused me to follow closely every twist and turn. For me it was the prospect of our electing a woman president that was the most important and exciting aspect of her candidacy, not to mention the fact that I agree with her on most issues.

How do you feel about art in the age of Trump?
Going forward will be tough for me as a cartoonist. For one thing, I am sick and tired of making jokes about Trump. There’s nothing funny about him anymore. He was kind of fun to draw, and easy—the hair, the mouth, the hands, etc,—I usually managed to capture him with a few quick strokes of my pen. But I was really hoping to have a break from doing it. (Hillary was tougher to draw—no question.) But people need to laugh—especially now. So that will continue to be my job in the age of Trump.


Leah Goren
(Commissioned by Cup of Jo)

This illustration was commissioned a couple weeks before the election, assuming a Hillary win. The premise of the article was to be responses from 10 female illustrators on Hillary's election, which left room to make it very personal. I only sent one sketch, because I knew this was the direction I wanted to go. It was painted with gouache on paper and then scanned into Photoshop. Sometimes I do a lot of assembling or editing in Photoshop, but these drawings were painted as is, minus a few tweaks.

Did you feel personally involved in her campaign?
No, I've never felt too politically engaged. Moving forward, that is changing.

How do you feel about art in the age of Trump?
I think art is just one part of the bigger picture, but it's also so important to continue to share big ideas and personal stories, and art, design, and illustration is a beautiful way to reach people.


Ward Sutton

I created a lot of work critical of Trump in 2016. But I felt that it wasn’t enough to be anti-Trump, but that people needed to be pro-Hillary. I devoted time to create this positive image and put it out there for free.

What to you was most exciting about her potential win?
Obama was elected with such sky-high expectations that no mortal could live up to. Hillary, by contrast, would have had exceptionally low expectations going in, while also having amazing experience and political skills. I think she had the potential to be a tremendous success as president. Also, it’s high time we had a woman in charge!

Have you met Hillary?
In the fall of 1998, I had the good fortune to be invited to Opening Night at Carnegie Hall with my wife, Sue Unkenholz. We sat at the back of the hall in the second balcony. Suddenly, just before the show was to begin, every head in the entire hall turned back toward us. But it wasn't to see us, obviously; it was to see Hillary, who had just arrived and was sitting directly below us in the first balcony. We craned our necks and could see her merely a few feet away. Seeing that entire crowd facing not the stage but the back of the hall, it really made an impression on me about what kind of life Hillary has lived. Also: The Starr Report had just been released days earlier.

After the concert, Hillary was the key speaker at the reception. When she took the podium, each table in the dining room had one or two people who refused to stand up or clap for her. It was striking. She proceeded to deliver a flawless, passionate speech about the importance of art in public life. She did not appear rattled at all.


Rebecca Clarke

Did you feel personally involved in her campaign?
I did not feel even 10 percent as involved as I had felt with Bernie, and by the end felt okay about voting for Hillary. I made a Trump drawing as well, and it was pretty easy to achieve his likeness, but his expression is not a sympathetic one, so drawing him churns my stomach. I would say Hillary is more satisfying to draw.


Tara Jacoby

This was done within an hour. I was trying to make something quickly that would portray her with poise, strength, and confidence.

How do you feel now that it won’t be used for her victory?
Temporarily disheartened.

What to you was most exciting about her potential win?
The possibility of her being able to finally shatter the glass ceiling. And even though she lost, I believe she made a rather large crack, which has inspired many other women to try and break through it.

How do you feel about art in the age of Trump?
Although I'm not looking forward to drawing his mug for the next four years, I do think that he has inspired some iconic, politically and emotionally charged art. I think that artists will use their art to fight for what they believe in, and it will be beautiful.

Have you met Hillary?
I'm still waiting for her to respond to my DM.