Trump doesn't merely resemble former Prince Andrew — he surpasses him, overwhelmingly

The Department of Justice's release of Jeffrey Epstein-related documents has been chaotic, disorganized and suspect, but nonetheless has done what such disclosures always do: pull familiar names back into view and remind us who associated with the late financier and sex offender.

Among those recurring characters are the former Prince Andrew and Donald Trump, two men whose ties to Epstein have long been known and whose denials of wrongdoing are by now familiar.

At first glance, their fates could not seem more different. Dig a little deeper, though, and parallels between Andrew and Trump become eerie enough to make one wonder whether they might be, as the saying has it, brothers from different mothers.

Arising from the latest Epstein disclosures, Andrew is alleged (assumed) to have sent an email to Ghislaine Maxwell, Epstein’s jailed partner in sex-trafficking crime, asking if she has found him “inappropriate friends.”

Andrew hasn’t commented but the email raises an obvious question: in Epstein and Maxwell’s predatory world, what could “inappropriate” plausibly mean?

The disclosure that Trump flew on Epstein’s plane eight times, despite his repeated claims he never did, forces a similar reckoning. Innocent people generally do not lie about such things.

Or seek to avoid accountability. Andrew’s laughable attempts to avoid being subpoenaed in perhaps the most famous case arising from the Epstein affair are a case in point, as are Trump’s endlessly contorted explanations for why he ended his friendship with Epstein.

What is not funny are the lives Andrew and Trump constructed before their links to Epstein became a liability.

Both were shaped by senses of entitlement without accountability. Think of Andrew’s disastrous BBC interview, his insistence he could not sweat. Think of Trump’s lifelong refusal to admit error under any circumstance.

Each was the indulged son of a powerful family, raised to believe rules existed for the little people: the bourgeoisie, or low-income Black tenants in Queens.

Andrew was famously Queen Elizabeth II’s favorite, shielded and indulged well into adulthood. Trump was the beneficiary of Fred Trump’s money, protection, and affirmation, even as he repeatedly failed.

Had Fred Trump not rescued his son from collapse in Atlantic City through a shady bailout, Donald Trump would be toast.

Andrew prospered thanks to his mother’s status the way Trump rode his father’s coattails.

Andrew’s fall from grace was rooted in confusing royal status with substance. He drifted through palaces owned by his family or by foreign monarchs, trading on his title but producing little of value. His travel expenditures as U.K. special representative for trade and investment were so excessive, he earned the nickname “Air Miles Andy.”

Luxury was not something earned. It was something he assumed he deserved. When public funds and official allowances no longer sustained his lifestyle, he turned to wealthy benefactors and opaque financial arrangements that never aligned with his income or role.

Trump’s story is about bone spurs, bankruptcies, and brand inflation — all with the same entitlement, all without responsibility. He marketed himself as a titan of riches while living in perpetual overextension, propped up by licensing deals, loans and foreign capital, and a half-rate reality show.

Now, his dizzying approach to foreign policy becomes easier to understand if you simply follow the money and the gifts. Nothing has changed, except Trump’s day job.

The White House increasingly resembles an American Buckingham Palace. Trump’s obsession with gold fixtures, furniture, clocks, trophies, and décor betrays deep insecurity about wealth he did not earn.

These displays are not examples of success. Like Andrew’s perks, they are received through proximity to power. Neither man has shown much interest in where the extravagance comes from.

Both men were drawn to foreign money, particularly from Arab states. Andrew’s reliance on wealthy Gulf patrons became obvious as his official standing diminished. He was reportedly offered safe harbor in Abu Dhabi, should he be kicked out of the U.K. He courted Saudi princes with the desperation of a man whose access was slipping but whose appetites were not.

Trump’s relationships make Andrew’s look like child’s play. Trump has lavished praise on Crown Prince Mohammed bin Salman while explaining away the murder of Jamal Khashoggi, a Washington Post journalist and U.S. resident, by the Saudi regime in 2018.

The motivation is obvious. Ask Trump’s son-in-law Jared Kushner, whose business was revived by a grotesque two-billion-dollar Saudi investment.

Andrew was ultimately banished when the overlap between private indulgence and public disgrace became impossible to defend. His brother stripped him of titles and duties. Prince William has reportedly signaled that when he ascends the throne, he will “deal with” Andrew.

Trump faces no such mechanism. The U.S. has no crown to remove from a man who crowned himself. Trump treats the presidency not as a public trust but as a personal palace. The boundaries between governance and self-enrichment have all but vanished. Policy, diplomacy, even “America First” — all are filtered through personal benefit.

In that sense, Trump does not merely resemble Andrew. He surpasses him, overwhelmingly. He is royal without restraint, with no obligation to constitutional authority. Without shame, he ignores laws about foreign involvement.

Finally, both men have long emphasized that they neither drink nor smoke, as if abstention is some kind of redeeming quality. It is not. In their cases, it only sharpens the contrast between public restraint and private indulgence: sexual scandal, compulsive behavior, profound disregard for women.

It’s what Adam Ant sang in “Goody Two Shoes”: “Don't drink, don't smoke, what do you do?/ Subtle innuendos follow/ There must be something inside…”

The symmetry of these two men is uncanny. Both born into privilege, protected by powerful families, obsessed with status, drawn to predators, dependent on foreign money, fixated on women, convinced accountability is for the little people.

Separated at birth, or simply brothers from other mothers?

• John Casey was most recently Senior Editor, The Advocate, and is a freelance opinion and feature story writer. Previously, he was a Capitol Hill press secretary, and spent 25 years in media and public relations in NYC. He is the co-author of LOVE: The Heroic Stories of Marriage Equality (Rizzoli, 2025), named by Oprah in her "Best 25 of 2025.”