By Jeremy Kinsman

November 12, 2025

Dreamy, ludicrous comparisons are sometimes made between the Trump presidency’s “Make America Great Again” nativist fig-leaf and the 1920s Jazz Age of fun and flappers.

When President Trump hosted a Mar-a-Lago “Gatsby” party on Halloween for a slew of well-heeled, well-connected guests, scolds saw an unsavoury contrast between what was billed as a “nostalgic fantasy about a bygone era,” and the plight of the 40 million poorest Americans who risked losing their food-support benefits in the government shutdown.

The more literary-minded see the Mar-a-Lago gala as a total misunderstanding of Fitzgerald’s 1925 masterpiece The Great Gatsby, cited by late Cambridge scholar Tony Tanner as “the most perfectly crafted work of fiction to have come out of America” (he died two decades before the Trump presidency).

“A Little Party Never Killed Nobody,” a song from the soundtrack of Baz Luhrman’s 2013 The Great Gatsby, was both the evening’s tag line and the White House response.

Scott Fitzgerald wrote his parable as a depiction of an America careening toward self-destruction in an inequality bubble. Gatsby’s parties were drawn as exhibitions of excess, and ill-gotten wealth, where partygoers, “safe and proud above the hot struggles of the poor,” displayed obscene indifference to the want that many Americans suffered.

They included, “young Englishmen dotted about; all well-dressed, all looking a little hungry, and all talking in low, earnest voices to solid and prosperous Americans…agonizingly aware of the easy money in the vicinity and convinced it was theirs for a few words in the right key.”

Tanner wrote “to the extent that Jay Gatsby is excessive, foolish, and foredoomed, so, the whole book suggests, is America. Fitzgerald knows, of course, exactly what he is doing. He wants to show America desecrated, mutilated, violated.”

The parallels between then and now are tempting. Adam Hochschild made a vivid connection in the concluding pages of American Midnight, his compelling account of the early 1920s, described in The Philadelphia Enquirer as “a cautionary tale of what happens when democracy goes off the rails.”

Hochschild writes: “During Donald Trump’s presidency, the forces that had highlighted the America of a century earlier would be dramatically visible yet again: rage against immigrants and refugees, racism, red-baiting, fear of subversive ideas in schools…beyond all of them is the appeal of simple solutions: deportations, forbid critical journalism, lock people up, blame everything on those with a different color or religion.”

Scott Fitzgerald wrote his parable as a depiction of an America careening toward self-destruction in an inequality bubble.

Fitzgerald believed that Americans habitually took their identity from an embellished past while expending their energies on an abundant future, leaving unaddressed the problems of the present. Recourse to a misremembered past is a reflexive theme of today’s populist nationalist leaders. As Gatsby famously says, “Can’t repeat the past? Why of course you can!”

Will the U.S. repeat the past of a hundred years ago? In his Great Depression re-telling 1929, Andrew Ross Sorkin documents how easy money and corruption in the Jazz Age, and de-democratization of the economy, morphed into a bubble and the transformational economic crisis of the Crash of 1929.

It was preceded by multiple precursors in mood and attitude of today’s America, including the Johnson-Reid Act that reduced immigration by 95%, and the 1917 Espionage Act,  which permitted surveillance of Americans, government crackdown on political dissent and oppositional press, troops in the cities, and the arrest by the Justice Department of thousands on the grounds of “radical beliefs”.

The Crash of 1929 did lead to an array of protective regulatory safeguards in finance and commerce to prevent a recurrence, including the Banking Act of 1933, known as Glass-Steagall, whose repeal in 1999 enabled the merging of commercial and investment banking, a deregulatory hinge moment whose contribution to the 2008 financial crisis is being debated still.

Today’s markets are again showing signs of the “irrational exuberance,” that Federal Reserve Chairman Alan Greenspan cautioned against in 1996. The Trump Administration has loosened regulatory oversight, while pumping up the U.S. deficit to a historic high of $38T, (125% of GDP), which could prove unsustainable in a world in disorder.

Most of the rest of the world is aghast at the direction the U.S. Administration is taking internationally: the daily litany of recoil-prompting, swaggering deviancy from the re-defection from global climate change discussion (“the biggest scam in history” — Trump at the UN), and from the G20 (because Trump maintains the host country, South Africa, is causing a “genocide” of white farmers. The US has accordingly allocated them the bulk of 2025’s pitiful number of 7,500 US asylum admittees, down from 100,000 in 2024). Trump’s arbitrary, unilateral tariffs on all and sundry are eviscerating the global trading regime that provides the economic infrastructure of the rules-based international order.

But could US political ground be shifting against Trump’s vision? Declining approval ratings, grassroots momentum from recent “No Kings” mass demonstrations of seven million Americans, and off-year electoral results boosting Democrats suggest it could well be. Will Trump see an adverse trend and adapt to meet it, or will he try to crush it, like he did the White House East Wing, an act of vandalism which seems to have evoked a public respect for the symbols of American democracy in ways he didn’t expect?

Fitzgerald’s description of Tom and Daisy Buchanan as avatars for entitled 1920s elites does ring a bell: “Careless people,” who “smashed up things and creatures and then retreated back into their money or their vast carelessness, or whatever it was that kept them together, and let other people clean up the mess they had made.”

If today’s power elites misconstrue America’s past, it could doom them to repeat it — as Fitzgerald foretold in his parable’s closing line:

“So, we beat on, boats against the current, borne back ceaselessly into the past.”

Policy Contributing Writer Jeremy Kinsman was a Fitzgerald scholar at Princeton whose thesis was on “Gatsby and the American Dream.” He was much later Canada’s ambassador to Russia, high commissioner to the UK, ambassador to Italy, and to the European Union. He also served as minister at the Canadian Embassy in Washington. He is a distinguished fellow of the Canadian International Council.