Top 10 Donald Trump Moments That Are Disturbing Because of What We Know Now

#10: Getting Roasted For His Presidential Ambitions (2011)

“Comedy Central Roast of Donald Trump” (2011)

Before Donald Trump was a political figure, he was a punchline, and nowhere was that clearer than at his 2011 Comedy Central Roast. That night, a parade of comedians and celebrities took turns skewering the real estate mogul over his ego, bankruptcies, and, in what now feels downright prophetic, his supposed lack of fitness for the presidency. At the time, jokes about “President Trump” — imagine that! — landed as pure absurdist humor, the kind of gag that worked precisely because it seemed impossible. In hindsight, the roast plays less like harmless ribbing and more like a surreal warning: the world laughed at the idea… right up until it stopped being a joke.

#9: His Thoughts on Bill Clinton’s Most Infamous Scandal (1998)

“Hardball with Chris Matthews” (1994-)

Long before setting foot in the Oval Office, Donald Trump had no problem weighing in on presidential scandals. In a 1998 appearance on Hardball with Chris Matthews, he offered his take on the Bill Clinton–Monica Lewinsky saga, calling it “terrible” and an “embarrassment,” and criticizing the president’s judgment. Coming from Trump, the moral posturing now lands with a thud: two decades later, he’d become the only U.S. president to be impeached twice, once for abuse of power and once for incitement of insurrection. In hindsight, his Hardball commentary feels less like punditry and more like a case study in irony, proof that history doesn’t just repeat itself, it occasionally smirks while doing it.

#8: Claiming He Probably Wouldn’t Run For President (1988)

“The Oprah Winfrey Show” (1986-2011)

In a 1988 interview with Oprah Winfrey, future president Trump confidently told her he “probably wouldn’t” run for the nation’s highest office — though he didn’t shy away from outlining political views that resurfaced in his campaigns. He criticized America’s trade deals, lamented the state of the economy, and positioned himself as a blunt outsider who could “fix” things if he ever chose to. Over a decade later, in a 1999 “Larry King Live” appearance, he even floated Winfrey as a potential running mate. In hindsight, those offhand remarks look like an early draft of a campaign pitch he’d eventually take all the way to the White House.

#7: Airing His Disillusionment With the American Political Establishment (1999)

“Larry King Live” (1985-2010)

When Donald Trump appeared on “Larry King Live” in 1999 to discuss a potential presidential run, he painted himself as a political unicorn: too liberal for Republicans, too conservative for Democrats. Most surprising in hindsight: his emphatic support for universal health care, calling himself “quite liberal” on the issue and insisting a country’s worth hinged on caring for its sick. He also rejected isolationism, but demanded fair treatment from foreign nations. Fast-forward to his eventual presidency, and these positions — like so many in Trump’s career — had shifted, sometimes completely, leaving the “Larry King” interview as a time capsule of views he’d later abandon or reverse entirely.

#6: The Things You Can Supposedly Do When You’re a Star

“Access Hollywood” (1996-)

Few political scandals have detonated with the force of the Access Hollywood tape. Released mere weeks before the 2016 election, the 2005 recording captured Donald Trump making remarks widely condemned as an admission of assault. At the time, more than a dozen women had already accused Trump of misconduct, and the tape seemed like it might end his campaign outright. It didn’t. In the years since, the footage has only grown more disturbing in light of what’s come out: multiple new allegations, high-profile lawsuits, and a jury in 2023 finding Trump liable for abusing and defaming writer E. Jean Carroll. What once looked like a career-ending revelation now reads as the opening act in an ongoing pattern.

#5: His 2000 Presidential Run

Various

In many ways, Donald Trump’s brief 2000 presidential bid foreshadowed the populist outsider brand he’d successfully ride to the White House in 2016. He railed against “corrupt” politics and commanded headlines through sheer force of personality. At the time, he distanced himself from extremist figures in the party, blasting Pat Buchanan, David Duke, and Lenora Fulani for their perceived political affiliations. That makes his later trajectory all the more jarring: in the run-up to and during his presidency, Trump openly courted and emboldened white nationalist support. Far from a joke or publicity stunt, his 2000 campaign proved his presidential ambitions were both real and long-running, years before the world took them seriously.

#4: Going Full Birther

“The View” (1997-)

Sitting alongside the hosts of “The View,” Trump doubled down on a growing fixation: demanding that President Barack Obama produce proof of his United States birth certificate. This wasn’t just idle skepticism: it was part of Trump’s central role in promoting “birtherism,” a baseless conspiracy theory that claimed Obama wasn’t born in the U.S. and was therefore ineligible for the presidency. Critics rightly pointed out its racist undertones, as it sought to delegitimize America’s first Black president. Though thoroughly debunked, Trump’s birther crusade kept him in the headlines and cemented his standing with a certain faction of the electorate, laying the groundwork for the political brand he’d carry into 2016.

#3: “Very Fine People”

Aug. 15, 2017 Press Conference

In August 2017, the “Unite the Right” rally in Charlottesville, Virginia ended in violence and the killing of counter-protester Heather Heyer. Donald Trump’s response became one of the defining moments of his presidency. While he did eventually condemn neo-Nazis and white supremacism, his infamous assertion that there were “very fine people on both sides” was widely seen as granting legitimacy to extremist movements. In hindsight, the moment feels like a grim preview of January 6th, 2021, when a mob of Trump supporters stormed the U.S. Capitol in an attempt to overturn the election. In the years after Charlottesville, Trump’s willingness to pardon right-wing extremists only underscored the degree to which he had emboldened the fringe.

#2: Trump vs. Barack Obama &... Seth Meyers

2011 White House Correspondents’ Dinner

The 2011 White House Correspondents’ Dinner is remembered less for President Obama’s jokes than for Seth Meyers’ merciless roasting of his eventual successor, who sat stone-faced in the audience. At the time, Trump was in the midst of his high-profile “birther” crusade, making him an irresistible target. The “Weekend Update” host’s monologue killed, and the room roared. Trump didn’t. In retrospect, the moment feels like a turning point: a public humiliation that some speculate fueled his determination to run for president in 2016. What played as late-night fodder at the time now reads as the prologue to one of the most consequential — and divisive — campaigns in American history.

#1: His Close Friendship With Jeffrey Epstein

Various

Donald Trump’s long and well-documented friendship with financier and convicted sex offender Jeffrey Epstein is a stain on his public image that only deepens with time. Photographs place them together at parties stretching back to the 1980s, often surrounded by young women. One particularly damning clip from a 1992 party shows Trump and Epstein laughing and chatting, with Trump whispering something into Epstein’s ear before the two share a knowing grin. While Trump has since claimed they had a “falling out,” court records and testimony suggest their social circles overlapped for decades. In light of Epstein’s arrest and subsequent death, the footage now plays more like an uncomfortable reminder of the company Trump was willing to keep — and defend — until it became politically untenable.

Which Trump moment on our list shocked you the most? Are there any prescient moments we missed? Be sure to let us know in the comments below!