The Stories Behind Donald Trump’s TIME Covers

I am often asked who’s been on the cover of TIME the most over the past 100 years. I usually reverse the question and ask them who they think. This typically elicits responses ranging from Queen Elizabeth to Jesus to Taylor Swift. And while those three choices combine for 35 TIME covers, they fall far short of the all-time record holder. More on that later.

In August 2020, longtime TIME cover artist Tim O’Brien and I were concepting a cover image of Donald Trump floating away amid a sea of COVID-19. It would be the fourth in a series of painted covers from O’Brien depicting Trump in a growing storm within the Oval Office.

And, at the time, I naively thought it would be our last cover on Trump — a total that would end at 35.

“The magnitude of outrageous behavior and events all seemed to build towards that final Trump image of him among the COVID virus,” says O’Brien, who has painted more TIME covers in the past 30 years than any other artist. “The series used water rising to eventually take him out of the Oval Office. Now that he’s back in, nothing much changes with the job I do.”

TIME would publish 65 Trump-less TIME covers before the former and future President returned in an iconic, graphic presentation following his 34-count indictment in April 2023. Edel Rodriguez’s “thumbprint” portrait of Trump won the Best Political Cover from the National Magazine Awards.

“By condensing his look down to the basic elements, done through color, one could focus more on the concept behind the image or what the President symbolized, rather than what he looked like,” says Rodriguez, who worked as TIME’s international art director in the 1990s and has illustrated nine TIME covers featuring Trump. “I think a typical caricature, where the artist makes fun of a person’s weight or other characteristics, can be easily dismissed. I strive to make images that bypass all of that and hit closer to the bone.”

Trump has always had a fascination with TIME. He first landed on the cover on Jan. 16, 1989, 28 years before his inauguration, with the headline “This Man May Turn You Green With Envy – or Just Turn You Off. Flaunting It Is His Game, and Trump Is his Name.” His continued interest was evident during his first full day as commander-in-chief when Trump, standing in front of a memorial to intelligence agents killed in the line of duty, told a gathering of national security officials, “I have been on their cover like 14 or 15 times. I think we have the all-time record in the history of TIME magazine. If Tom Brady is on the cover, it’s one time because you won the Super Bowl or something, right? I’ve been on the cover 15 times this year. I don’t think that’s a record that could ever be broken.”

For the record, he had been on 11 TIME covers at that time and Tom Brady has never been on TIME’s cover. Today, Trump’s total cover count now stands at 43 - only three shy of Ronald Reagan and 12 from TIME’s record holder, Richard Nixon. (This, of course, does not include the fake TIME cover that was reportedly hanging in at least five of his golf clubs, with a cover line exclaiming that “Trump is hitting it on all fronts … even TV!” The existence of the bogus covers, first reported by the Washington Post, prompted TIME to ask the Trump Organization to remove them. Several real TIME covers currently hang in various locations inside his Mar-a-Lago residence.)

Eight of the 10 people who have appeared most often on TIME’s cover are U.S. Presidents. After Nixon, Reagan, and Trump, the rest of the top 10 are Bill Clinton (40), Barack Obama (31), George W. Bush (30), Jimmy Carter (27), Jesus (22), and Hillary Clinton and George H.W. Bush (21 each).

We first introduced candidate Trump to TIME’s readers in August 2015, when photographer Martin Schoeller and TIME editor-at-large Paul Moakley brought a live bald eagle to the Trump Tower in New York City for a portrait. The eagle was particularly animated during the photo and video session, prompting Trump to exclaim at one point, “I love TIME magazine. What you will do for a cover … this bird is seriously dangerous and beautiful.” A clip of the bird nipping at the Republican candidate went viral.

During the 2016 campaign, we worked with Rodriguez to produce seven covers featuring Trump and create an original visual language for this President. Rodriguez has a strong, simple, graphic style that immediately grabbed worldwide recognition with the “Meltdown” cover (Aug. 22, 2016), a reflection of Trump’s slumping campaign following the Republican National Convention. Two months later, in response to the release of the infamous “Access Hollywood” tape, Rodriguez followed with an updated image. “Total Meltdown” received the 2017 Cover of the Year award from the National Magazine Awards.

Rodriguez follows decades of creative work addressing the American presidency. David Levine depicted Lyndon Johnson as Shakespeare’s King Lear (Jan. 5, 1968), an illustration that Levine said at the time was the “best metaphor for a man beset with problems.” Mike Hinge created a foreboding graphic portrait of Richard Nixon with the headline “The Push to Impeach” (Nov. 5, 1973). Mort Drucker caricatured President Gerald Ford and House Speaker Carl Albert as hapless doctors trying to revive a deathly ill economy (Jan. 27, 1975). TIME presented a diminutive photo of Clinton under a bold headline “The Incredible Shrinking President” (June 7, 1993). President George Bush sported a lipstick kiss and a black eye on a Dec. 1, 2003, cover with the words “Love Him, Hate Him.”

The range of visual approaches we’ve used to depict Trump over the years underscores the way we tailor our cover presentations to fit the story. He was chosen as TIME’s Person of the Year in 2016, with the cover portrait shot by Nadav Kander, and in the years that followed, we presented him as a frenetic Twitter user crumbling the Washington monument (March 20, 2017), a punching bag (Oct. 9, 2017), a graphic wrecking ball (Nov. 6, 2017), an angry character with his hair on fire (Jan. 22, 2018), a cross between himself and Vladimir Putin (July 30, 2018), a king looking into a mirror (June 18, 2018), a slingshot-holding fighter dueling with Nancy Pelosi (Jan. 21, 2019), a happy President whistling under an umbrella in the rain (April 8, 2019), and a man who has painted himself into a corner (Oct. 7, 2019).

“Events call for visual explanations,” adds O’Brien. “Can a visual still have impact? Will irregular behavior be highlighted or just expected? We will see. It might be a busy next four years.”

The Trump covers show how the design of the TIME cover has adapted to the changing social media landscape, where millions view the cover today.

“I was surprised at how successfully the images were used and how well they translated on a variety of media, from television to YouTube, Instagram, and Twitter,” said Rodriguez. “This made me realize how much of a cultural object a magazine cover can be at this time. You can’t hold up a digital image. A magazine has weight, scale, it marks history.”

Our Trump covers have not been without debate. An image we created of Trump staring down at a young immigrant girl for our “Welcome to America” cover (July 2, 2018) sparked controversy. The President also continues to share on social media a fake TIME cover animation of our “How Trumpism Outlasts Trump” cover from Oct. 22, 2018.

“TIME covers remain, through all the changes in media prominence and ways with which people get their news, a powerful mark of where the national conversation is,” says O’Brien. “The sharing of a cover is a way for people to offer their take on where we are, and in return, perhaps offers a bit of catharsis in the act.”

At a dinner for the TIME100 in 2019, Jared Kushner, the son-in-law of President Donald Trump, asked me a question: “What is your favorite TIME cover of my father-in-law?” I don’t normally like to pick a favorite cover. I would rather not single out one from among the nearly 1,000 TIME covers I’ve designed and produced over the past two decades. But I did answer Kushner’s question. 

My favorite TIME cover of Trump is “Nothing to See Here” from Feb. 27, 2017. I believe the strongest TIME covers leave space for a variety of perspectives. As I told Kushner, “If you’re an opponent of your father-in-law, you look at that cover and see all the chaos this man has created. And if you’re a supporter, you look at it and say even among the chaos in Washington, look at how resolute he is. That is a great place for a TIME cover to be.” He agreed.