New Yorker Illustrator Tom Bachtell Talks Trump, Clinton, and Obama

By Stephen Raskauskas |

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Tom Bachtell’s self-portrait (c) Tom Bachtell

Even if you don’t know the name Tom Bachtell, you know his work. For over 20 years, the Chicago-based illustrator has been a regular contributor to The New Yorker, which includes his drawings and caricatures in “The Talk of the Town” each week.

You may also have seen Bachtell’s art in other publications including The New York Times, The Wall Street Journal, Entertainment Weekly, Newsweek, Forbes, and Bon Appetit.

Bachtell spoke with his friend and long-time Chicago Sun-Times columnist Laura Washington about his wide-ranging career as an illustrator, and in particular, what it’s been like to portray figures like Barack Obama, and of course, the two current presidential nominees: Hillary Clinton and Donald Trump.

Hear their conversation on WFMT Monday, October 3, 2016, at 10:00 pm, or anytime by clicking below. Below, you can also enjoy some of the illustrations Bachtell mentions in their conversation, along with an edited transcript of excerpts from it.

Tom Bachtell: The “Talk of the Town” section has a couple of different components and there is comment – which is essentially an editorial – and from week to week that’s usually a political topic, or are about a political person. And of course this year it’s intensely so. And so there’s a lot going on.

Laura Washington: And you do a lot of portrayals of figures. And the two figures we have this time around in the presidential race are historic in many ways: Hillary Clinton and Donald Trump. Everyone’s so confused about this election, and you’re laughing, so how have you approached this especially through your work?

Bachtell: I’m having a hard time processing things. This is kind of a surreal season I think for everybody and for me as well. I think that over time I tend to try to get to know figures that I draw and if I’m lucky I get a chance to draw them several times, and so it’s a sort of a continual process. And honestly, in the case of Donald Trump, you know he’s really difficult for me to draw for many reasons. And I’m just glad that I’ve had a chance to take a few shots at him.

Hillary & Trump Post DNC TB200dpi

Illustration by Tom Bachtell for The New Yorker

Washington: Can you talk a little bit more about why it’s been difficult. Is it is politics is it him. Is it the way he looks something else.

Bachtell: Well it’s kind of the whole package because we’ve never had anybody like this run for president before. And in some ways, he’s kind of the culmination of sort of some of the worst aspects of American culture. You know he’s ultimately a salesman and he’s selling himself and his business and he’s self-involved and he’s, to my mind, ignorant and he sort of celebrates that. I mean there is a lot that sort of on the surface that you might think is kind of humorous. But on the other hand, the idea that somebody like this could become president is also really scary and horrifying. And so it’s kind of hard to reconcile that. I think when I’m doing portraits because I tend to like to create drawings that are on some level kind of amusing and lively. But I can’t always. And so it’s in his case it’s particularly hard.

Washington: And you most recently did a piece on him that connected to Shakespeare. Tell me a little bit about what happened with this particular piece.


Illustration by Tom Bachtell for The New Yorker

Bachtell: So the piece was about poetry that has inspired or been inspired by both Trump and Hillary. So that kind of took it a little bit out of the political realm I think. Right away I knew that I could kind of have a little bit of fun with it. There is reference in the piece to Shakespeare, so I kind of took that as a jumping-off point and sort of tried meld him with Shakespeare a bit. And then once I got to the hair you know I was thinking it would be fun just to post some of my outtakes some of the drawings that didn’t get used because I did so many different kinds of combinations of sort of Shakespearean hair, but with you know an elaborate comb-over. It just kind of gave my imagination some free rein and it ended up being fun. I probably had more fun drawing him than I have in a while.

Washington: So what are the steps week by week?

Bachtell: We have a pretty tight schedule at The New Yorker and I have weekly deadlines. I do either two or three drawings per issue and the drop-dead deadline is Friday afternoon and I usually get the “Talk of the Town” pieces on Wednesday, so I will have usually have two days to do those drawings. Then the comment piece, I will often know what the general topic is probably by Wednesday, sometimes Thursday. Often nothing’s written until Friday.

Hillary Double Standard TB

Illustration by Tom Bachtell for The New Yorker

So a lot of it’s happening in real-time and my art director is very good and she gets as much information to me as she can as quickly as possible. And if there’s text for it she’ll get that to me sometimes. Obviously, the text is very helpful to doing the drawing.

In the case of the Trump Shakespeare, there was text for that. So I was able to read that and I think maybe that may have come in on a Wednesday. And so I had a day to draw that. And then they fortunately liked one of the things I sent which doesn’t always happen, but in this case, they did. I don’t think that I really I didn’t have to do significant changes.

Now because of the New Yorker‘s online presence which is very strong and very sophisticated, and it’s kind of a slightly separate entity, I have to actually reformat the drawings. The drawings that are in the magazine are vertical. The drawings that are online are horizontal so I have to kind of make some quick changes and do that as well now and that’s but that’s just that’s part of our new, modern world.


Trump Pre-ConventionPlaneTB

Illustration by Tom Bachtell for The New Yorker

Bachtell: Every piece I draw really is kind of starting over starting fresh and whether it’s Trump or Hillary or anybody. Sometimes it’s often people I don’t know very well and I have to get to know them very quickly. I think a lot of my drawing is a process of getting to know somebody. So there’s a sketching process which involves often looking up things online about people, reading about them, studying pictures, studying video clips, maybe trying to collect stories about them. I want to try to get into their world and I try to do a fresh take every time.

Say with Trump, there may be some particular expression that I’ve noticed and I want to try to capture that because I have never quite gotten it. That’s usually a pretty quiet process but it’s probably a good third of the process you know in terms of time.


Hillary The Choice 2016 by TB 200dpi

Illustration by Tom Bachtell for The New Yorker

Ideally, it takes place at least over the course of two days so I can sleep on it. If I can start that process, really think about a person, then start doing sketches and then and then I kind of have an internal…I guess I don’t know if it is dialogue or monologue it’s probably it’s by a dialogue as I’m talking to just talking to myself.

One of the questions I often ask myself is, “If you saw this person from across the street, you would instantly recognize who that is. Why?” We would recognize Trump from a mile away. What are those things? What are those little signifies that jump out? Some of them are the shape of his body, his head, his hair, the way he carries himself. You can also do that in terms of the face that actually helps me to kind of simplify the face. What are the first things that you kind of notice? Then I can kind of emphasize that.

Washington: That’s interesting you say that because obviously you want the reader to get it immediately. But you’ve also got to avoid it being a cliché. How do you guard against that or do you care?


Donald Trump Globe by TB

Illustration by Tom Bachtell for The New Yorker

Bachtell: Oh no, I do care. It’s part of this sort of internal dialogue. Another question I will often ask myself is, “Why not?” You know if I have an impulse to try to draw something of quality there are times when I have to encourage myself to go for it and try it.

Washington: Then someone like Barack Obama, who has been president for nearly eight years and given the content of “Talk of the Town” and given what the New Yorker does, there’s probably been hundreds of portrayals of Obama by magazine maybe even by you. How do you keep it fresh? How do you make it different? [To see some of Bachtell’s many portrayals of Obama, click here.]

Bachtell: I’ve drawn him so many times and I never get tired of it. I think that has to do with I think the way we relate to people. If you want to get to know somebody, you never get tired of trying to find out new things about them. Right? We’re always kind of looking, and I think that’s true with somebody like Obama. I’ve loved drawing him over the years. There have been times when he was very challenging to me. And I kind of learned after a while to relax a little bit I think with him when I got some of the sort of some of the features down.

Hillary Benghazi Hearings by TB

Illustration by Tom Bachtell for The New Yorker

Washington: Did that make you nervous, because he’s an African-American president there may be more sensitivities to the portrayals. I remember back way back during the campaign when a New Yorker ran that very controversial cover which I know you didn’t do. Are you worried about getting into trouble?

Bachtell: That’s a good question. When I first drew him, I think it was after he spoke at the 2004 convention (and it’s kind of interesting to see that right now because it’s so different than what I am doing). I do remember drawing him when The New Yorker endorsed him for president in 2008. And it’s such a cautious drawing. But a lot of that had to do with, I think, I was feeling a lot of caution from the editorial side. You know I had to say it’s a very idealized kind of portrait and it feels a little constrained to me.

You also asked another question which I think is a really good question that has to do with his features. I think my answer to that partly applies to almost everybody I draw. I think it informs some of the style of my drawing, but it helps a lot if I embrace everybody’s features. And realize, I love features. I love the shapes of people’s faces. I love the shapes of features and you know you might not think that it matters, but if you get into a state where you are celebrating features, or celebrating physicality, or what makes something interesting, it’s amazing how what it will do to a line.

Just look at Obama, I mean he has you know these beautiful full lips and that was you know that was something that I think that people were very kind of cautious about. In the old days when that was something that was a feature that would probably have been used in a derogatory way,  but there’s a beauty in them.

His nose is very distinctive. There’s a certain kind of broadness to it, but it also has an interesting sort of tip. It’s sort of rounded in a very distinctive way. And he’s got these beautiful nostrils. They have a very nice shape to them. And then he’s got oh I know there’s other things that I kind of go for. I like the shape of his hairline and his jaw.

Washington: You get it. You like it.

Bachtell: I like it.