An Artist Responds to Trump’s Cratering of America: A Q&A With Esteban Whiteside

Esteban Whiteside

Mueller's Breakfast (2016)

President Trump has hijacked America’s collective consciousness, fraying the bonds holding a volatile, multicultural nation together. There are as many daily outrages from him as there are hours in the day—and increasingly he utters some of the most nauseous paeans to white supremacy ever delivered by an American president.

When the president gets into Esteban Whiteside’s head, powerful and devastating images from the catalog of Trump’s travesties emerge. Whiteside’s works also reach back deep into the African American experience, retrieving shards of slavery, Jim Crow, and police brutality to hurtle them straight at the viewer.

There is no middle ground in these challenging tableaux. They force audiences into the tightest chambers of racism where most of the exits are blocked. Such is the power of Whiteside’s subject matter that his work captured the attention of filmmaker Spike Lee, himself a provocateur of the highest order, who featured three of Whiteside’s works in Season 2, Episode 3 of She’s Gotta Have It, the Netflix series update of his 1986 classic movie.

In early 2020, the self-taught artist who hails from Marion, North Carolina, near Asheville, will have his first solo show in Washington, D.C. Whiteside, who also doubles as The American Prospect’s communications specialist, spoke to me about his work. This conversation has been edited for length and clarity.


Gabrielle Gurley: Many Americans are on edge with a loud and proud racist in the White House. What is the role of the artist at this historical moment?

Esteban Whiteside: I can’t speak for other artists, but I feel like I have a duty. I remember when Michael Brown got killed [in Ferguson, Missouri] and I saw that image of him laying in the street—it was over 100 degrees and he was there for hours. Something changed and my artwork changed after that. At one point, I did paint abstracts [but] I couldn’t see myself painting flowers and beautiful things when there is so much bad stuff going on right now. I felt an obligation after to paint stuff that mattered to me, to black people and all oppressed people. Even if their artwork doesn’t speak to what’s going on right now, artists should still be involved with organizations that promote change.

How do you view political expression by artists since Trump took office?

I see a lot of artists who speak out about something, but their artwork really hasn’t changed a lot. They don’t want to want to ruffle any feathers or lose fans. A couple of years ago, I had an art show [in Washington], and the work got taken down because it was political and a lot of it was anti-Trump. [The venue owners] said mixing politics and alcohol was not a good idea: They felt that someone was going to get drunk and destroy the work. Some artists think about that when they put out their work: If it is not going to be shown anywhere or it’s going to offend people, they stay away from it.

Describe how Trump has gotten into your head and what that has meant for you.

Since Trump became president, he messes up so much stuff from day to day that you can encapsulate many topics and issues all in one Trump painting. It’s just like putting a face on evil.

Tell me about one of your first works about Trump, White House Party #2. It features Trump officials like Ben Carson and family members like Ivanka and Melania to allies like Kanye West, Mitch McConnell, and Vladimir Putin. They are out on the White House lawn along with Klansmen, ICE agents, and others —66 figures in all. Meanwhile, Trump himself is framed in a window of a Russian onion-domed White House.

White House Party #2 is one of those pieces where I just wanted to cement those people that showed support for him. Years from now, a lot of those people are going to try to jump back on the right side of history and say [their support for Trump] was taken out of context. With this White House piece, I just put in every one [of his supporters] that I could think of—people [who were] on the Trump train at [that] moment.

Esteban Whiteside

White House Party #2 (2017)

Which characters are really powerful for you in this collage?

Kanye West really sticks out to me just because I loved him up until all this happened and he started showing support for Donald Trump. It was crazy and interesting to see how much he changed just by Donald Trump becoming president.

How did Kanye West change?

He turned his back on the people that got him there and made him who he was and turned his support to the person of power in the moment. They’re really similar: If you show Donald Trump or Kanye West any type of love in the moment, you’re their best friend. Once [the Trump presidency] is over with, Kanye will try to come back to the black community and say everything was taken out of context and that’s not really what I meant. It has definitely damaged his art. He’s not making the same high-caliber [work] that he was making before all of this.

Snakes figure in this work and frequently in your other pieces.

I like drawing snakes. When I see a snake, I immediately think evil. It just helps.

Why did you decide to do a painting of The Squad—Representatives Alexandria Ocasio-Cortez, Ilhan Omar, Ayanna Pressley, and Rashida Tlaib?

Esteban Whiteside

The Squad (2019)

I created this piece to combat all the lying, hateful rhetoric that Trump was spewing out at the Squad in his latest attempt to distract from the real issues in this country. I love the Squad and all they do, so this piece was a way to pay homage to them. They stand up for issues that really matter and because of that they were attacked.

“Concrete oppressionism” is the term you’ve created to describe your work. What does that mean?

A lot of the artists that I did like when I got into art were abstract expressionists like Romare Bearden. Some of the ideas in the artwork can be interpreted in a lot of different ways. I wanted my topics and subjects to be very polarizing, so you either like it or you don’t—there is no room for interpretation. Instead of the word “expressionism,” I wanted to use the word “oppressionism” because that is where all this work comes from, the idea that somebody is getting the short end of the stick or somebody is being oppressed.

You took on the subject of concentration camps at the southern border.

I just felt helpless that I couldn’t do anything directly about it. In the position I am in right now, one of the biggest things I could do is make a piece about it and post it and have thousands of people see it. It might not change the situation in the camps, but at least it’s letting people know that I am not OK with it, and that there are a lot of people that are not OK with it. And that there are people who are willing to speak out about it—that might motivate someone else to speak out in their own form of art or whatever they do.

Esteban Whiteside

Concentration Camps for Kids (2019)

What is the meaning of Hold Down the Negro, with its C-SPAN–style graphic and Republican and Democratic vote tallies.

The idea was to show all the Republicans for the bill to “Hold Down the Negro” and [show] a few Democrats in the numbers. I feel like that’s the blueprint for most bills and most things that happen. You have almost all the Republicans that are against black people and then you sprinkle a few Democrats in there. You can turn on C-SPAN any day, and there are things that are happening that are making your life harder.

Esteban Whiteside

Hold Down the Negro (2016)

Mueller's Breakfast recalls the 1987 anti-drug television public service announcement.

I first did this piece after Kellyanne Conway said, “alternative facts.” My mind automatically went to, this is your brain on alternative facts from the “this is your brain on drugs” commercial. Over time, I’ve changed the name, to Mueller’s Breakfast, the name has changed a few times. The idea of it was feeding into this crap is just as harmful as drugs.

Esteban Whiteside

Mueller's Breakfast (2016)

What is the sense of the United States you are trying to convey with The Flag? It’s almost like a portrait of the decline and fall of the U.S.

The idea was to show the way that I thought about the U.S. There were always things that were being revealed to me, that were letting me know the country’s true colors the older I got. With Donald Trump, the whole perception of America being portrayed as warriors for freedom, going around the world and helping people—all that’s out the window—it’s always been out the window but it hasn’t been exposed like it is now. The veil has been pulled all the way back and there is no more hiding.

Esteban Whiteside

The Flag (2018)

What drew you to art?

Just the honesty of it. Artists can go outside the lines of norms and speak their minds. Art can have more of an immediate impact on people. I can be way more truthful than I can be in real life or in person.

Washington is the seat of government and visitors can be surprised that it has such a vibrant local art scene or could serve as the source of inspiration for an artist. How did moving to Washington in 2014 influence your work?

Before I moved to D.C., in the city that I lived in, Marion, North Carolina, I never would have been able to paint any of this. Back in my hometown there were no galleries, no museums. If I painted, I would have had to explain myself nonstop and no one would have bought it. Moving up here, there were more educated, open-minded people who could appreciate the work.

You’ve worked as a museum assistant at the Phillips Collection here in Washington: Did the curators take an interest in your work?

They had an employee staff show which was the first art show that I was ever in. It was the first time I showed my work to anybody. I got good feedback, so that right there really pushed me to do more work. If I had gotten bad feedback, who knows what would have happened? They really thought that it was truthful and they thought it was strong work.

What are the challenges for a self-taught artist in the commercial art world?

There are polarized opinions about it: People either really appreciate self-taught artists and the art holds a special place for them, or people look down on self-taught work—folk art, basically. It’s even called “outsider artwork,” folk art is. From the beginning, it’s been pushed into its own lane. I don’t mind, because some of the first artwork that I saw was folk art. Just growing up [near] Asheville, there are a lot of folk art galleries there and in Appalachia. My brother went to school up there, so I saw a lot of folk art. That let me know that I could do this if I really wanted to do it. It doesn’t have to look like fine art.

Spike Lee showcased some of your pieces in the Netflix series She’s Gotta Have It. What does that kind of exposure mean for an artist?

I feel like it has already done a lot for my work. There was a gallery I applied for before the show: I paid application fees and just didn’t get accepted. Then I applied to the same gallery after the show and put that [experience] on my artist’s resume and I got accepted. Having somebody like Spike Lee co-sign it will change the perception [of folk art] in people’s minds to “Well, he likes it, then I can like it now.”

Michael Brown’s death changed your vision of what it means to be an artist. You have done a lot of painting on police brutality since then. Laquan McDonald has figured strongly in your works. What personal experiences with police brutality have you had?

Esteban Whiteside

Heart (2017)

I have only had bad experiences with cops. I had a 323 BMW when I was in college and the first day [that I drove it], I got pulled over. And on the second day I got pulled over, and maybe three weeks later, I got pulled over. And every time it happened, [a white cop wanted to know] “Where did you get this car?” “Where do your parents work?” That was when I started hating the police.

Another time, my friend, a white guy, pulled into my neighborhood to pick me up. We were going down the road and we got followed by a white cop. The cop pulled us over. The cop didn’t say a word to my friend; all he said was, “Why were you coming out of that neighborhood?” And me, he asked to see my ID, and I wasn’t even driving. I got upset. At that point, it wasn’t in my head that a cop could shoot you, kill you for anything.

I was being really outspoken, cussing and telling him, “I’m not showing you my ID. I’m not driving; this is bullcrap. My mom, we are going to come up to the police station tomorrow! You can’t do this.” [The cop] ended up going back to his car. We had to sit there for an hour. Then he let me and my friend go and nothing happened.

The very next day, the cop called me personally and called my friend and apologized—because my friend’s dad was really high up in a manufacturing plant in the town and everyone worked there. He was the human resources manager and I bet some of the cop’s relatives worked there and he realized who it was and called me to apologize. When I tried to talk to him, he had already hung up the phone.

Were you surprised by that?

I was surprised that he called and I was also surprised that he apologized. That just showed me a power dynamic in the town that I was just oblivious to.

Because if you hadn’t been with a white friend, anything could have happened?

Yeah, anything could have happened. Exactly.

Esteban Whiteside

Esteban Whiteside with his dogs, Francis and Pablo.


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