Playboy, fighter, golfer and wearer of a George Washington wig: Donald Trump’s greatest magazine covers
The US president has called his latest Time magazine cover ‘the worst of all time’. We found some he may hate even more – and others pivotal to his rise
In a turn of events that may surprise some, Donald Trump expressed a few relatable insecurities this week. First he questioned the attractiveness of his beach body, then he blasted Time magazine for an unflattering cover photo. In fairness, he wasn’t wrong. He called the picture, taken from below, “the worst of all time”. People have focused on the wattle neck, the gossamer hair, the inside of his nostrils.
The question he asked of the editorial decision was actually a pertinent one. “What are they doing, and why?” This is the kind of scrutiny that the press should attract, except that media literacy is dying a fast death – and that has a lot to do with Trump himself. Constantly lambasting Pulitzer prize-winning publications as “fake news” and then retweeting Photoshopped images and deep fakes isn’t helping the situation.
Here are some past memorable Trump covers – some of which he admired, and others which, in no uncertain terms, he did not.
Time, 2024
This is no doubt a cover much more to the President’s liking. Love him or despise him, it’s undeniable that standing up mere seconds after a bullet grazes the side of one’s head and yelling “Fight, fight, fight!” is a brave move. Crazy maybe, but brave. The photo of that moment, shot by Evan Vucci, will go down as one of the most significant images in political history.
Time and Trump have a turbulent relationship. He famously mocked up covers of himself to hang at four of his golf clubs, which resulted in the magazine writing to the President to ask him to remove them (and a pillorying cartoon from The New Yorker). The magazine has issued a number of memorable covers of Trump, including an illustration of stormy conditions in the Oval Office, and one of his golf cart stuck in a bunker.
One of his more recent Time covers was when he was named Person of the Year – a title Trump has received twice. (Although he once claimed he had turned it down, Time magazine denied it in a statement.) Before Trump entered the White House for the first time, he had only featured on the cover of the magazine once, in 1989. But in 2017 he falsely claimed to have been on the cover more times than anybody else. In fact Richard Nixon and Ronald Reagan at that time surpassed him.
On the second occasion he received his Person of the Year designation, Trump said: “Well, thank you very much. This is an honor, a tremendous honor.” (Up for debate, when previous recipients include Adolf Hitler and Josef Stalin.) He was pleased too with one Time cover, brandishing it at a rally in Des Moines. “They used to call it the ‘Man of the Year,’ but they can’t do that anymore. They call it ‘Person of the Year.’ It’s the same thing. That’s fine. But look at that – that’s a good-looking cover.”
Esquire, 2004
While Trump may not have featured on the Time cover very much pre-politics, he did feature on many others as New York’s brash, publicity-seeking business mogul and Manhattan social scene fixture. Trump is obsessed with gold. He loves bling. It makes sense then that Esquire would kit him out in medallions and rings galore. Also shout out to the accompanying cover lines of: “Wild tales of strippers! Streakers! Tsunamis! Leopard Attacks!” Talk about something for everybody. And note the other feature: “The Case for Bush”. This is not, in fact, an editorial on pubic hair, but about George W.
Oh, and the strap for the Trump story? “How I’d Run the Country (Better)”. Indeed, Trump’s first mention of his wish to achieve the highest office was circa 1987. Turns out we should have taken him both seriously and literally.
C 41, 2016
An extremely innovative cover from the Milan-based magazine dedicated to all things design and style. Layering the cover with a Trompe-l’œil style technique (pun possibly intended), the magazine’s gallery arm put on an exhibition entitled American Change, in which this cover, created by Japanese artist Kensuke Koike, features. A copy of the magazine was also included in the London Design Museum’s Hope to Nope show.
There are other similarly themed covers; Trump’s mouth is rather a subject of fascination. Note that impressionists will first attempt to nail his voice; then the second thing is the puckering of the mouth. Recently, the queen of the Netherlands was caught mocking Trump’s lip movements – a bold move given he was standing right next to her. Some might liken the general aesthetic of this particular maw to a cat’s bum, but that wouldn’t be me. What is good about this cover is it is a departure from the usual way cover designers depict Trump’s mouth – which is black text across his philtrum to resemble a Hitler moustache. It’s been done, guys. Many, many times.
Vanity Fair, 2024
In the past few years outlets have taken to producing digital covers for online readers. This was a striking one in 2024 from Vanity Fair, not just for the pore-intense close-up, but the directly presented set of numbers down the lefthand side. Can’t really complain when the facts add up. The cover went viral on its release, with millions of likes and views on X alone.
Trump has a history of beef with Vanity Fair. In particular with its former editor, Graydon Carter, who once referred to Trump as “a short-fingered vulgarian”. In turn, Trump has called Carter “a real loser”. Trump has often dissed the magazine on social media, and in 2016 tweeted: “Has anyone looked at the really poor numbers of @VanityFair Magazine. Way down, big trouble, dead! Graydon Carter, no talent, will be out!” He was right about the last part – but Carter stepped down in 2017, staying on longer than intended to cover the beginning of Trump’s administration.
Internazionale, 2017
The matryoshka doll design isn’t super original, but this is very well executed from the progressive weekly Internazionale, which translates long-form articles from around the world into Italian. The implication of the cover is clear, and the detail is such that one doesn’t need the fully exposed face of Putin to recognise him. We can spot those thin lips and filler-enhanced cheeks anywhere.
Bloomberg Businessweek, 2016
Perhaps the most unsettling of the bunch, courtesy of a 2016 Chinese edition of Bloomberg Businessweek. Trump likes to assert his reputation as a great businessman, which is questionable given his multiple bankruptcy filings. Nevertheless, he is currently receiving praise for his brokering of the Gaza ceasefire. (Maybe he listened to the audiobook of The Art of the Deal to brush up on his skills.)
The cover line translates to: “Donald Trump is a modern political Steve Jobs, turning his US presidential campaign into a one-man show.” This would have pleased Trump no end, as he seemed to have something of a crush on Jobs, tweeting many times about him in glowing terms. Except for when he declared: “I’ve always been a fan of Steve Jobs … but the yacht he built is truly ugly.”
Trump, however, is very much not a fan of Steve Jobs’ widow, who holds shares in The Atlantic, opining that the late Apple designer would “not be happy” about Laurene Powell Jobs “wasting money” on the publication. (Powell Jobs also donated $930,000 to the 2020 Biden campaign.)
Playboy, 1990
Trump is back in his playboy era here – literally. We know Trump is keen on this cover because he was pictured holding and signing the magazine not too long ago. (A signed copy is available on eBay for $4,000.) The truth is he does look good here. The suit is a much better fit than the one he wore to Buckingham Palace in 2019 – although true confirmation can only come from Menswear Guy.
In the cover interview, which you can read here, Trump appears to rule out a future run for the presidency – despite the topic being raised precisely because of his previous musings. Speaking about himself in the third person, he told the outlet: “The presidency? No, that takes an election, and it is clear that Trump is not that patient.”
Trump will probably not be too happy to hear that Hugh Hefner’s son has said that his father “regretted” the cover. Speaking to The Hollywood Reporter in 2017, Cooper Hefner said: “We don’t respect the guy. There’s a personal embarrassment because Trump is somebody who has been on our cover.”
New York, 1992
The funniest thing about this cover is that the tie makes Trump look for all the world like he goes to an underperforming British comprehensive school. The tie is screaming Geography second period. And the stance? Organised fight behind the maths block at the end of last bell. The reason Trump has to “scramble off the canvas” to quote the subhead, is that in the late 80s Trump seemed down and out. As Politico has described it, the businessman “lost his mind” and “sowed the seeds of his near-ruin” with catastrophic financial choices. But if there’s one thing Trump has proved, it’s that he has staying power. He is the human embodiment of Chumbawamba’s biggest (only) hit.
New York, 2015
Is there a headline that has aged worse than “Donald Trump Is Saving Our Democracy”? Probably not, what with him trying to organise a coup against the elected government.
Trump’s hair is one of the most recognisable things about him, so this cover, digitally manipulated so he’s wearing wear a coiffed wig in emulation of George Washington, is quite the deviation. And while the reference to the founding father is obvious, the look does slightly veer towards nan’s perm.
The above two examples aren’t the only New York editions featuring striking covers of Trump. The “Loser” strap line is one, for which the magazine issued an online explanation. And there’s this one, which aged about as well as the Washington one.
Libération, 2016
There’s nothing equivocal here. The left-leaning Libération melds what some might consider two of New York’s most famous villains, with Trump channelling Patrick Bateman. There’s also a touch of The Godfather. The French periodical is not the only publication to have referred to Trump on its cover as the Bret Easton Ellis character, with the New Statesman doing the same.
In terms of unsparing assessment, a competitor could be Die Welt’s no-nonsense strap line “Das Ende Der Welt” on a 2016 cover, which I feel even non-German speakers can take a stab at understanding. That was a great cover, featuring Trump as a roaring streak of anger in comet-form on track to consume the earth. Illustrated by Edel Rodriguez, it won a top prize at the Art Directors Club Germany awards. The magazine and Rodriguez followed up with a much more controversial and perhaps ill-judged cover of the President decapitating the State of Liberty.
The Economist, 2018
One for the pop culture aficionados. In 2013 Miley Cyrus’s certified banger Wrecking Ball (taken from the accurately titled album Bangerz) was riding high in the charts – and she was riding a giant wrecking ball in the music video. Memes abounded at the time, but five years on the Economist took inspiration and came out swinging with this cover. I’m not sure Trump suits the cherry Doc Martens that Cyrus wore in the video, but props to the illustrator Ben Kirchner for including them. And it is not impossible he does own the real thing – the singer auctioned the boots off for charity. The accompanying cover story you can read here.
The New Yorker, 2016
The symbol for the Democrats is a donkey and for the Republicans an elephant. The former has an association with Andrew Jackson (opponents called him a “jackass”), and the latter with Abraham Lincoln (“seeing the elephant” was a term used by soldiers during the Civil War). It’s a clever cover from The New Yorker to depict how Trump cleaved apart the old school GOP. It’s safe to say the Never Trump movement has failed abysmally – and now there are masked men dragging people off the street and it’s horrifying. But don’t forget: with the circus trick, the subject of the sawing is a volunteer.
The cover was illustrated by the New Yorker’s own Barry Blitt and given the title “Grand Illusion”. Blitt said it was the fourth time in less than a year he had drawn the President. There is a gallery of Blitt’s previous Trump covers here.
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