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For the Feb. 27 cover of TIME on the chaos surrounding the initial days of the Trump administration we turned to Brooklyn-based artist Tim O’Brien. A long-time TIME collaborator, O’Brien’s work has appeared on over two dozen TIME covers since 1989, with subjects ranging from Pope Benedict XVI to Osama Bin Laden. His imaginative style and gift for detail made him the right choice to create a portrait of disruption in the White House.

“Painting this cover was like imagining a movie,” O’Brien said. “I see it all in my head, the swirling rain, the wind blowing papers across the desk, the splats of the heavy raindrops on the desk. The e-mail from [TIME Creative Director] D.W. Pine asked if I could paint Trump in a storm. As soon as he asked I saw the image. A cartoonist might get the subject to react, to animate, hold on and grimace in the face of the wind. I saw it more as a dead pan look at us. In paintings, it is the contrast that creates the interest, in this case, the calm and the chaos.”

Outside of his 28-year relationship with TIME, O’Brien’s work has appeared in publications all over the world, including several U.S. postage stamps and book covers such as the popular Hunger Games trilogy.

Two of his TIME magazine covers – one with Bill Clinton and Bob Dole and the other with the Grand Old Populists, both published in 1996 – reside in the National Portrait Gallery at the Smithsonian in Washington, D.C.

Watch O’Brien work in virtual reality as part of a recent TIME story, Virtual Reality is For Artists.