You are given a time machine to travel back to four discrete points in recent history, each time assuming the form of another human, in order to prevent Donald Trump from ever becoming president.
1987
You become the cover designer of Trump’s first book, The Art of the Deal. The original cover portrays Trump with Central Park in the background, looking every bit a confident Master of the Universe. Just before the book goes to press, you swap it out for a candid photo you took of a sick Trump blowing his nose into a much-used Kleenex. No one at the publishing house vets the new cover in advance, nor does the author, who is irate at the damage it will do to his public image.
But Americans find the shot unexpectedly relatable, Trump is praised for revealing himself in such a vulnerable light, and the book, with its instantly iconic cover, sells even better than expected. Embraced by the working class as he never has been, he runs for president in 1988 with a pledge to “cure the common cold of American politics” and defeats Michael Dukakis in a landslide.
2004
You become Jeff Zucker, president of NBC Entertainment. Trump pitches you the reality show The Apprentice. You emphatically turn it down, telling him it’s an awful idea and seemingly ensuring that he doesn’t further burnish his disingenuous bona fides as a business genius.
Irate over NBC’s rejection, Trump reworks his pitch and sells it to Bravo, albeit with a new focus on entrepreneurial ideas within the clothing industry. The Fashion Apprentice becomes an immediate hit with the network’s core audience of gay men and heterosexual women who work in media. Bolstered by these unlikely constituents, he runs for president on a third-party ticket later that year and crushes George W. Bush and John Kerry.
2011
You become William M. Daley, Barack Obama’s chief of staff. Before that year’s White House Correspondents’ Association dinner, you pull your boss aside.
“I don’t think you should roast Donald Trump tonight,” you say.
“C’mon, it’s funny!,” Obama says. “I’ll be a regular Bill Cosby.”
“I … wouldn’t compare yourself to Bill Cosby.”
“Are you kidding? He’s America’s most beloved celebrity, popular with everyone, from older men to younger—”
“No!” you exclaim.
The rules of the time machine forbid you from revealing to anyone the nature of your journey.
“Please, just don’t tell jokes about Trump,” you urge him. “I can’t explain why, but it will have tragic ramifications for America.”
Obama trusts you implicitly, and he not only omits any mention of Trump in his remarks but, fearful of imperiling the nation, proceeds through the event without any humor at all.
Trump, sitting among the restless audience, is irate that Obama has delivered such a dry speech. He resolves to run for president, believing he will be a far funnier presenter at a future White House Correspondents’ Association dinner. Honing his sensibility in unannounced stand-up gigs around the country, he becomes steeped in the era’s ironically detached sensibility and develops a brand of “anti-comedy” that appeals to cosmopolitan hipsters. With this unexpected base, he completely overturns Obama’s advantage among the 18-to-34-year-old, college-educated demographic in liberal cities and wins the presidency in 2012.
2015
You become Hope Hicks, Trump’s press secretary. Right before he descends his golden escalator in Trump Tower to announce his candidacy, you surreptitiously untie one of Trump’s shoelaces.
As Trump is about to get off the escalator, his loose shoelace becomes caught between the bottom step and the floor, and he cannot extricate himself. A technician is summoned to turn off the escalator, but the shoelace is still trapped, so an irate Trump must cut it with a scissors. The mortifying episode, depicting a bumbling man imprisoned by his own gaudy apparatus, is a ripe visual metaphor for out-of-touch ineptitude and appears destined to sink his fledgling campaign.
Knowing he must account for the blunder, Trump ditches his planned disparaging comments about Mexican immigrants and pretends that the incident was intentional, turning it into an extended allegory about “the pitfalls of ignoring those who are lowest in society” (the overlooked, untied shoelace), “disrupting politics as usual” (stopping the escalator), and “cutting the red tape of bureaucracy” (snipping the shoelace).
Without a platform built on xenophobia, a broad spectrum of pundits hail him as a candidate who can unite a profoundly polarized America with his rare combination of liberal, conservative, and anti-Establishment values. Leaning into this persona, Trump receives so much admiration across the country that he not only has no political need to tailor his message to racists and sexists but no longer feels the childhood pain of being unloved by his father, which eventually drove him to hateful vengeance.
He wins the presidency in 2016 after Hillary Clinton, who acknowledges that he will clearly be the best leader for all Americans, drops out. He is re-elected in 2020, again unopposed. A unanimous Congress and all 50 state legislatures vote to amend the Constitution to allow him to run for—and win—a third term.
In 2024, Trump, now bored with the job after eight years, becomes irate and turns America into a soft autocracy-cum-oligarchy.
Teddy Wayne is the author of several novels, including The Winner
