Donald Trump, the 45th President of the United States, has created an interesting and often rocky relationship with the press. It’s no surprise that his presence has headlined many magazine covers along this rainbow road. His image has been featured on the cover of many national and international publications, including such legendary publications as Time magazine, Vanity Fair, and Playboy. From his first Time cover in 1989 to digitally manipulated images depicting him in historical wigs, Trump’s appearances reflect both his personal brand and his evolving public persona.
Trump’s first appearance on the cover of Time magazine came in 1989. This was the start of what would become a very active and influential media landscape. Where he has gone off the deep end is on his number of appearances. On that note, Trump has bragged that he has been on the cover of Time more than anyone else. This assertion has no factual basis.
While he was achieving great publicity success in the late 1980s, he matched that with growing financial disaster. His unsuccessful investments led to at least four business bankruptcies. His critics said he had “gone mad” and “harvested the crop of his own destruction.” These personal economic hardships were a far cry from his subsequent claim to fame and fortune as one of the leading entrepreneurs of the venture capital industry.
During his entire career, be it in television or real estate, Trump has been anything but timid in expressing his feelings toward media moguls. His fraught relationship with Graydon Carter, then editor of Vanity Fair, is a perfect manifestation of this orbit. Otherwise, Trump has condemned Carter as “a real loser” and Carter is best known for calling Trump a “short-fingered vulgarian.” This exchange shows just how combative their exchanges have been, as well as President Trump’s love of the fight.
Apart from the critiques he levelled at others Trump’s own image has been a source of both adoration and derision. His hair has evolved into perhaps his most distinguishable characteristic, now a constant source of mockery and satire. A creative spin animated a digitally manipulated photo of Trump with his self-remodeled hair, styling a George Washington wig on an old magazine cover. This ingenious design cements his place as a cultural bogeyman, making him the object of both veneration and derision.
Trump’s love gold Another matter of Trump’s gilded persona that has been previously reported on. Indeed, this preference fits perfectly with his ostentatious lifestyle and public displays of wealth. And to be sure, he’s quite fond of making jokey asides about other characters. A memorable example of this came in the form of when he berated the queen of the Netherlands.
For all his controversies, Trump has said some nice things about tech magnate Steve Jobs. So far, he’s tweeted positively about Jobs at least a half dozen times and previously tweeted that he has “always been a fan.” This admiration coexists with his criticisms of Jobs’ widow, Laurene Powell Jobs, whom he accused of “wasting money” on The Atlantic, illustrating Trump’s complex relationship with influential figures in various industries.
Whether we’re talking Vanity Fair or Rolling Stone, Trump’s portrayal on magazine covers has a history of terrible optics. On other covers he is depicted with a toothbrush mustache in the style of Hitler. This intentional decision by these satirical outlets underscores their rebuke of his political agenda and identity. Additionally, there have been instances where Trump produced fake magazine covers featuring himself on the cover of Time, blurring the lines between reality and self-promotion.
Fast forward to 2021, and no one is denying Trump his mental gymnastics for demo purposes, allowing him to look back at his time in media’s spotlight. In a 2024 interview with Time magazine, he expressed gratitude for being featured again, stating:
“Well, thank you very much. This is an honor, a tremendous honor.” – Donald Trump
He continued to discuss the significance of magazine covers in popular culture:
“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.” – Donald Trump
These screeds remind us both that Trump is more alive than ever in media discourse and that he still harbors a deep desire—even need—to influence public perception.