Donald Trump has spent years attacking Vanity Fair magazine.
He has dismissed it as elitist, irrelevant, and emblematic of a cultural class he claims to despise. In December 2016, just weeks before taking office, he publicly lashed out at the magazine after it published a scathing restaurant review, accusing it—once again—of being part of a rigged and hostile media establishment.
This antagonism was not new. Decades earlier, Spy magazine—co-founded by Kurt Andersen and future Vanity Fair editor, Graydon Carter—had positioned Trump firmly outside the circle of cultural admiration, memorably dubbing him a “short-fingered vulgarian.” The phrase was less an insult than a diagnosis: it acknowledged Trump’s wealth, ambition and swagger while denying him the cultural approval he clearly desired.
That history matters.
Vanity Fair’s recent publication of Christopher Anderson’s portraits of senior members of the Trump White House drew immediate and widespread attention, circulating rapidly and prompting sharp scrutiny for their exposed, unvarnished quality. Many viewers read the photographs as awkward, revealing and humiliating. But focusing on how the photographs have been received misses what they reveal beneath the image.
The subjects of this shoot—White House Chief of Staff Susie Wiles, White House Press Secretary Karoline Leavitt, Vice President J.D. Vance, Secretary of State Marco Rubio, Deputy Chief of Staff for Policy Stephen Miller, Director of the Presidential Personnel Office Dan Scavino, and Deputy Chief of Staff for Legislative, Political, and Public Affairs James Blair—were not reluctant or resistant subjects. They willingly participated in the aesthetic grammar of a magazine their leader has repeatedly attacked. That choice reveals far more than the photographs themselves.
Participation, in this context, is a form of alignment. It is an acceptance of framing, tone and audience. To agree to be photographed is to accept the terms of visibility set by the artist or institution offering the attention. The act of showing up matters as much as what the camera captures. Once that choice is made, the photographs no longer simply function as portraits. The results become records of how power is positioned—and what it reveals in the endeavor.
Christopher Anderson’s photographs in Vanity Fair allow us to observe President Trump’s senior staff attempting to occupy a space long denied to him: the realm of cultural legitimacy. The magazine created a setting in which the desire for cultural legitimacy became visible. And that is precisely why the photographs are so unsettling.
Cultural authority works differently from political power. Power can be seized, claimed and enforced. Cultural belonging cannot. It emerges slowly, through shared ideals, respect, recognition and time spent inside a community that confers meaning. You cannot arrive there by insistence or appointment.
Now, people may reject an institution publicly while still longing for its validation privately. In fact, hostility often masks attraction. You don’t rail against something repeatedly unless it matters to you. Seen through this lens, Christopher Anderson’s photographs read less as portraits of people in power and more as each subject’s bid for recognition, and the approval from a cultural class that has heretofore refused to administer it.
Once exposed, yearning—particularly if there is any whiff of desperation—dissolves any illusion of cultural significance. Of any sense of “cool.”
This is where Vanity Fair’s editorial intelligence becomes unmistakable. The magazine did not need to editorialize, scold or condemn. It simply created the conditions for a contradiction to reveal itself. These subjects—individuals accustomed to wielding power who nevertheless wanted to be seen as belonging somewhere better—completed the gesture by agreeing to appear.
The result recalls Spy’s original acumen: the most effective cultural critique does not attack. It observes, reports and reveals. The “short-fingered vulgarian” endured not because it was cruel, but because it named a truth Trump himself could never escape—that money and dominance do not automatically confer taste, ease, or belonging.
Christopher Anderson’s photographs operate in the same tradition. They show us power stripped of bravado; its subjects embedded with something far more human and vulnerable: the need to be accepted by the very world they claim not to need. This inherent contradiction is what makes them so effective, and so remarkable.