The Stories Behind Donald Trump’s TIME Covers

At a dinner for the TIME 100 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 more than 700 TIME covers I’ve designed and produced over the past 12 years. But I did answer Kushner’s question. More on that later.

Trump, whose presidency comes to end this week, 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.” At the time, Trump had been on 11 covers. He did not then, nor does he now, hold the record of most TIME covers. More on that later too.

Since before his election, Trump regularly politicked to be named TIME’s Person of the Year (he was recognized as such in 2016), using campaign rallies and his now-locked Twitter feed to comment on TIME’s choices. And perhaps most notably, fake TIME covers were designed to hang in his golf course clubhouses, with cover lines 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 TrumpOrganization to remove them.

TIME has a long history of featuring presidents on the cover and Trump, whose presidency defied precedents and fractured norms, has been no exception. Eight of the top 10 people to appear most often on TIME’s cover are U.S. presidents. Trump finishes his term with 35 TIME covers, the fourth most of any president behind Richard Nixon’s 55 covers, Ronald Reagan with 46 and Bill Clinton with 40. Rounding out the top 10 are Barack Obama with 31, George W. Bush (30), Jimmy Carter (27), Jesus (22), and Hillary Clinton and George H.W. Bush tied at 21.

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 produced seven covers featuring Trump and created an original visual language for this president with the artwork of artist Edel Rodriguez. Rodriguez, who worked as TIME’s international art director in the 1990s, has a strong, simple, graphic style that immediately grabbed worldwide recognition with the “Meltdown” cover (Aug. 22, 2016), a reflection of his 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 American Society of Magazine Editors.

“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 illustrated seven 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.”

Some covers call for more straight-forward treatment, putting a moment in its historical context. Such was the case for Trump’s 2016 election night win and subsequent inauguration. Other covers, capturing moments like impeachment, call for a more critical lens, for which TIME worked with artists and illustrators since its inception.

Rodriguez follows decades of creative work addressing the American presidency. David Levine depicted Lydon 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 under 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 underneath 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.”

Which leads me back to 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.

That image was created by longtime collaborator Tim O’Brien, who has painted more TIME covers (33) in the past 30 years than any artist. It was the first of what would become a series of four paintings from O’Brien depicting Trump in a growing storm within the Oval Office.

“I don’t generally do cartoonish images, so faces are often neutral and the situation is revealed through the ridiculous analogies,” says O’Brien, whose cover series included “Stormy” (April 23, 2018), “In Deep” (Sept. 3, 2018) and “The Plague Election” (Aug. 17, 2020).

“To me, that is enough, and puts a cover image in a zone where the viewer can apply their thoughts to the matter.” The “Stormy” cover, a response to Trump’s scandal involving Stormy Daniels, was named Adweek’s Cover the Year for 2018.

“The past four years were emotionally draining for most people. While I stressed over most of Trump’s actions in office, I was not as bothered with him as I was with his enablers,” says O’Brien, who ended up painting eight TIME covers featuring the president. “I knew Trump, being a New Yorker. It was all those who turned a blind eye that shook my faith in the guardrails. There is a cover idea in there, somewhere.”

The variety of our visual approaches on the cover underscores the variety of what TIME covers. In the past three years, we presented the president 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).

We’ve also photographed Trump for multiple covers, including a White House tour (one day before the firing of James Comey) for our May 22, 2017 cover, and an Oval Office conversation in the summer of 2019 on Trump’s effort to keep the White House. That cover, photographed by Pari Dukovic for TIME, had Trump sitting on the resolute desk in the Oval Office with the quote, “My Whole Life is a Bet.”

The Trump covers show how 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 tweet a fake TIME cover animation of our “How Trumpism Outlasts Trump” cover from Oct. 22, 2018.

As the events of last year unfolded, aside from a couple of covers questioning his response to the growing pandemic, Trump’s image on the cover took a backseat to frontline workers, racial injustice protests and the rising Covid numbers. And even though his time left as president can now be counted in hours, it’s certainly possible that we haven’t seen the last of him on the cover of TIME.

“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,” adds 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.”

Before Kushner and I ended our brief conversation that night, I asked him a question: “Which cover would you say is your father-in-law’s favorite?” He thought for a second, and said “I don’t know. I’ll have to ask him.”