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From one-off moments to future scandals, these moments take on new meaning with hindsight. Join us as we examine presidential statements, interviews, and public appearances that reveal questionable patterns in light of what would come later.
Transcript
00:00Welcome to WatchMojo, and today we're counting down our picks for the moments that proved
00:12eerily prescient in predicting the rise of future President Donald J. Trump.
00:16So many of the things I say, now politicians are saying, hey that's right, why aren't
00:22they paying us?
00:25Number 10.
00:26Being roasted for his presidential ambitions, Comedy Central Roast of Donald Trump.
00:46Before Donald Trump was a political figure, he was at Punchline, and nowhere was that clearer
00:50than at his 2011 Comedy Central Roast.
00:53That night, a parade of comedians and celebrities took turns skewering the real estate mogul
00:59over his ego, bankruptcies, and in what now feels downright prophetic, his supposed lack
01:05of fitness for the presidency.
01:16At the time, jokes about President Trump, imagine that, landed as pure absurdist humor, the kind
01:23of gag that worked precisely because it seemed impossible.
01:26In hindsight, the roast plays less like harmless ribbing, and more like a surreal warning.
01:32The world laughed at the idea, right up until it stopped being a joke.
01:35And now you're going to run for President, don't you think that's a really cool idea, you guys?
01:39You'll keep him honest, you'll keep him honest, Donald.
01:42Personally, I hope you win, because I can't wait for the assassination, I mean the inauguration.
01:47Number 9.
01:49His thoughts on Bill Clinton's most infamous scandal, Hardball with Chris Matthews.
01:52I would have done something certainly different than what they did, I mean that all started
01:56it.
01:57Paula Jones is a loser, but the fact is that she may be responsible for bringing down
02:01a president indirectly.
02:02And you know, that statement was a bad statement to have made, been made, and it's proven to
02:07be false.
02:08So...
02:09Which statement was that?
02:10I'm sorry.
02:11Paula Jones in the deposition.
02:12Long before setting foot in the Oval Office, Donald Trump had no problem weighing in on
02:16presidential scandals.
02:18In a 1998 appearance on Hardball with Chris Matthews, he offered his take on the Bill Clinton-Monica
02:23Lewinsky saga, calling it terrible and an embarrassment, and criticizing the president's judgment.
02:28Well, I think his little speech afterward was a disaster.
02:31It wasn't the right tone, and I'm not sure he should have done it.
02:34And I'm not even sure that he shouldn't have just gone in and taken the Fifth Amendment
02:36and said, look, I don't get along with this man-star, he's after me, he's a Republican,
02:40he's this, he's that, and you know, just taken the Fifth Amendment.
02:43It's a terrible thing for a president to take the Fifth Amendment, but he probably should
02:46have done it.
02:47But Trump, the moral posturing now lands with a thud.
02:51Two decades later, he'd become the only US president to be impeached twice.
02:56Once for abuse of power, and once for incitement of an insurrection.
03:00In hindsight, this hardball commentary feels less like punditry, and more like a case study
03:05in irony.
03:06Proof that history doesn't just repeat itself, it occasionally smirks while doing it.
03:11It's such an embarrassment to him.
03:12I mean, I see him walking around, it's like a terrible embarrassment.
03:15And you think when you see him doing this, what comes to your head as a businessman about
03:21the miscalculation he made?
03:22Well, it's just that there are so many miscalculations, and he's had such bad advice.
03:27It's just been so badly handled.
03:29Number eight, claiming he probably wouldn't run for president.
03:33You took out a full-page ad in major US newspapers last year, criticizing US foreign policy.
03:40What would you do differently, Donald?
03:42I'd make our allies, forgetting about the enemies, the enemies you can't talk to so easily.
03:46I'd make our allies pay their fair share.
03:48We're a debtor nation.
03:49Something's going to happen over the next number of years with this country, because
03:52you can't keep going on losing $200 billion.
03:54In a 1988 interview with Oprah Winfrey, future President Trump confidently told her he probably
04:00wouldn't run for the nation's highest office.
04:02Though he didn't shy away from outlining political views that resurfaced in his campaigns.
04:07He criticized America's trade deals, lamented the state of the economy, and positioned himself
04:12as a blunt outsider who could, quote unquote, fix things if he ever chose to.
04:17This sounds like political presidential talk to me.
04:20And I know people have talked to you about whether or not you want to run.
04:22Would you ever?
04:24Probably not.
04:25But I do get tired of seeing the country ripped off.
04:28Why would you not?
04:29I just don't think I really have the inclination to do it.
04:32I love what I'm doing.
04:33I really like it.
04:34Also, it doesn't pay as well.
04:35Over a decade later, in a 1999 Larry King live appearance, he even floated Winfrey as a
04:41potential running mate.
04:42In hindsight, those offhand remarks look like an early draft of a campaign pitch he'd
04:47eventually take all the way to the White House.
04:49You've said, though, that if you did run for president, you believe you'd win.
04:52Well, I don't know.
04:54I think I'd win.
04:55I tell you what, I wouldn't go in to lose.
04:56I've never gone in to lose in my life.
04:58And if I did decide to do it, I think I'd be inclined.
05:02I would say that I would have a hell of a chance of winning.
05:04Because I think people, I don't know how your audience feels, but I think people are tired
05:07of seeing the United States ripped off.
05:09Number seven, airing his disillusionment with the American political establishment,
05:13Larry King live.
05:14Why would you leave the Republican Party?
05:17I think that nobody's really hitting it right.
05:20The Democrats are too far left.
05:22I mean, Bill Bradley, this is seriously left.
05:25He's trying to come a little more center, but he's seriously left.
05:27The Republicans are too far right.
05:29And I don't think anybody's hitting the chord.
05:31Not the chord that I want to hear, and not the chord that other people want to hear.
05:34And I've seen it.
05:35When Donald Trump appeared on Larry King Live in 1999 to discuss a potential presidential run,
05:41he painted himself as a political unicorn, too liberal for Republicans, too conservative for Democrats.
05:46Most surprising, in hindsight, his emphatic support for universal healthcare.
05:51Calling himself quite liberal on the issue, and insisting a country's worth hinged on caring for its sick.
05:57I'm conservative.
05:58Generally speaking, I'm conservative, and even very conservative.
06:00But I'm quite liberal and getting much more liberal on healthcare and other things.
06:04I really say, what's the purpose of a country if you're not going to have defense and healthcare?
06:09If you can't take care of your sick in the country, forget it.
06:13It's all over.
06:14I mean, it's no good.
06:15He also rejected isolationism, but demanded fair treatment from foreign nations.
06:20Fast forward to his eventual presidency, and these positions, like so many in Trump's career,
06:25had shifted, sometimes completely, leaving the Larry King interview as a time capsule of views he'd later abandon or reverse entirely.
06:33I would never lie.
06:34And I just, you know, one of the things that people do get if I ever decide to do this, which is really who knows, but they've known me for a long time.
06:41I've been really a public figure for a long time.
06:43I mean, I think everything is known about me.
06:45I mean, it's interesting.
06:46Yes, I would say.
06:47I've been out there a long time.
06:49But you could definitely say, I would not lie.
06:51I would not lie.
06:52I would absolutely not lie.
06:54Number six, the things you can supposedly do when you're a star, Access Hollywood.
06:59And I moved on her very heavily.
07:01In fact, I took her out furniture shopping.
07:03She wanted to get some furniture.
07:04I said, I'll show you where they have some nice furniture.
07:06I took her out furniture.
07:07I moved on her like a bitch, but I couldn't get there.
07:11And she was married.
07:12And all of a sudden, I see her, she's now got .
07:15She's totally changed her look.
07:16Few political scandals have detonated with the force of the Access Hollywood tape.
07:20Released mere weeks before the 2016 election, the 2005 recording captured Donald Trump making
07:26remarks widely condemned as an admission of assault.
07:29At the time, more than a dozen women had already accused Trump of misconduct.
07:34And the tape seemed like it might end his campaign outright.
07:37It didn't.
07:38I've got to use some Tic Tacs just in case I start kissing her.
07:41You know, I'm automatically attracted to beautiful.
07:43I just start kissing them.
07:44It's like a magnet.
07:46You just kiss.
07:47I don't even know what.
07:48And when you're a star, they let you do it.
07:50You can do anything.
07:51In the years since, the footage has only grown more disturbing in light of what's come out.
07:56Multiple new allegations.
07:57High-profile lawsuits.
07:59And a jury in 2023 finding Trump liable for abusing and defaming writer E. Gene Carroll.
08:05What once looked like a career-ending revelation now reads as the opening act in an ongoing pattern.
08:12A jury in New York finding Donald Trump, the Republican presidential frontrunner, by far liable for sexually abusing and defaming writer E. Gene Carroll.
08:24The jury also awarding the former magazine columnist nearly five million dollars in damages to be paid by Mr. Trump.
08:32Number five, his 2000 presidential run, various.
08:35I'm just asking.
08:36I mean, I saw you change party affiliation last week.
08:38You went over to the reform party.
08:39I did.
08:40And we're having a lot of fun and we're getting great response and we'll see what happens.
08:43When are you going to make a call?
08:44I would say probably in February.
08:46What's going to be the determining factors?
08:48Whether or not I can win.
08:49If I can win, maybe I'll do it.
08:51But is that going to be a result of polling or is that going to be a result of reception you get?
08:54Polling, just feeling.
08:55You know, everything I do, even buying this great building, this was feel.
08:58In many ways, Donald Trump's brief 2000 presidential bid foreshadowed the populist outsider brand he'd successfully ride to the White House in 2016.
09:07He rallied against corrupt politics and commanded headlines through sheer force of personality.
09:12I've put forward a proposal to pay off the national debt by imposing a one-time 14.25% tax on the super wealthy.
09:25At the time, he distanced himself from extremist figures in the party, blasting Pat Buchanan, David Duke, and Lenora Filani for their perceived political affiliations.
09:34The big thing they're going to look at is can you win?
09:37Can a Reform Party candidate win?
09:40Because I believe I could get the Reform Party nomination.
09:43I don't even think it would be that tough.
09:45It's going to be Buchanan.
09:46And I think Buchanan just blew himself out with the book and his love affair with Adolf Hitler.
09:50I mean, you know, how he said this is beyond belief.
09:53That makes his later trajectory all the more jarring.
09:56In the run-up to and during his presidency, Trump openly courted and emboldened white nationalist support.
10:02Far from a joke or a publicity stunt, his 2000 campaign proved his presidential ambitions were both real and long-running,
10:09years before the world took them seriously.
10:11Things can change.
10:15I'm in a city called New York City, where I spend most of my time, and I'll tell you that in the early 90s, New York City was in terrible, terrible shape.
10:30Number four, going full birther, The View.
10:34I was a really good student at the best school.
10:36I'm like a smart guy, okay?
10:37They make these birthers into the worst it is.
10:40Why doesn't he show his birth certificate?
10:42I think he probably—
10:43Why should he have to?
10:44Because I have to, and everybody else has to.
10:46Whoopi, why wouldn't he show his birth certificate?
10:49Excuse me.
10:50Sitting alongside the hosts of The View, Trump doubled down on a growing fixation,
10:54demanding that President Barack Obama produce proof of his United States birth certificate.
10:59This wasn't just idle skepticism, it was part of Trump's central role in promoting birtherism,
11:04a baseless conspiracy theory that claimed Obama wasn't born in the US, and therefore ineligible for the presidency.
11:11Why doesn't he show his birth certificate?
11:14And you know what? I wish he would, because I think it's a terrible pal that's hanging over him.
11:18He should show his birth certificate.
11:20The other thing, if you go back to my first grade, my kindergarten, people remember me.
11:25Nobody from those early years—
11:27That's not true.
11:28We have pictures of him.
11:29What are you talking about?
11:30Okay, show me a picture.
11:31Critics rightly pointed out its racist undertones as it sought to delegitimize America's first black president.
11:37Though thoroughly debunked, Trump's birther crusade kept him in the headlines
11:41and cemented his standing with a certain faction of the electorate, laying the groundwork for the political brand he'd carry into 2016.
11:48There's something on that birth certificate that he doesn't like.
11:51Oh my God.
11:52That's a terrible thing.
11:53That is just the worst thing that he was three pounds a day.
11:55I love you.
11:56I'm telling you.
11:57I love you too.
11:58I think that's the biggest pile of dog mess I've heard in ages.
12:01I love you too.
12:02Number 3.
12:03Very Fine People.
12:04August 15, 2017 press conference.
12:06I think there's blame on both sides.
12:08You look at, you look at both sides, I think there's blame on both sides.
12:13And I have no doubt about it, and you don't have any doubt about it either.
12:18And if you reported it accurately, you would say.
12:22In August 2017, the Unite the Right rally in Charlottesville, Virginia ended in violence
12:28and the killing of counter-protester Heather Heyer.
12:31Donald Trump's response became one of the defining moments of his presidency.
12:35While he did eventually condemn neo-Nazis and white supremacism, his infamous assertion
12:40that there were very fine people on both sides was widely seen as granting legitimacy
12:46to extremist movements.
12:47And you had some very bad people in that group.
12:50But you also had people that were very fine people on both sides.
12:56You had people in that group, excuse me, excuse me, I saw the same pictures as you did.
13:01You had people in that group that were there to protest the taking down of, to them,
13:07a very, very important statue.
13:09In hindsight, the moment feels like a grim preview of January 6th, 2021,
13:14when a mob of Trump supporters stormed the U.S. Capitol in an attempt to overturn the election.
13:19In the years after Charlottesville, Trump's willingness to pardon right-wing extremists
13:24only underscored the degree to which he had emboldened the fringe.
13:28You're changing history, you're changing culture, and you had people,
13:32and I'm not talking about the neo-Nazis and the white nationalists,
13:35the white nationalists, because they should be condemned totally.
13:38But you had many people in that group other than neo-Nazis and white nationalists, okay?
13:44Number two, Trump versus Barack Obama and Seth Meyers, 2011 White House Correspondents Dinner.
13:51We were working on these jokes for months.
13:53One of my guys said,
13:54Are you worried we're a little heavy on birth certificate jokes?
13:57What if he releases it before the dinner?
13:59The 2011 White House Correspondents Dinner is remembered less for President Obama's jokes,
14:04than for Seth Meyers' merciless roasting of his eventual successor, who sat stone-faced in the audience.
14:11Donald Trump has been saying that he will run for President as a Republican,
14:14which is surprising since I just assumed he was running as a joke.
14:20At the time, Trump was in the midst of his high-profile birther crusade, making him an irresistible target.
14:26The Weekend Update host's monologue killed, and the room roared. Trump didn't.
14:32Gary Busey said recently that Donald Trump would make a great President.
14:36Of course, he said the same thing about an old rusty birdcage he found.
14:45Donald Trump owns the Miss USA pageant, which is great for Republicans,
14:48because it will streamline their search for a Vice President.
14:51In retrospect, the moment feels like a turning point,
14:54a public humiliation that some speculate fueled his determination to run for President in 2016.
15:00What played as late-night fodder at the time now reads as the prologue
15:04to one of the most consequential and divisive campaigns in American history.
15:09Donald Trump said recently he has a great relationship with the blacks,
15:12though unless the blacks are a family of white people, I bet he's mistaken.
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15:30Number one, his close friendship with Jeffrey Epstein, various.
15:36Trump's wedding to Marla Maples in 1993 was dubbed the wedding of the century by the media at the time.
15:42And although we know that Trump and Epstein were friends during this period,
15:46this is really the first time that it's actually been reported that Trump invited Epstein to his wedding.
15:52This is, we should note, more than a decade before those first allegations of sex trafficking against Epstein.
15:59Donald Trump's long and well-documented friendship with financier and convicted sex offender Jeffrey Epstein
16:05is a stain on his public image that only deepens with time.
16:09Photographs place them together at parties stretching back to the 1980s, often surrounded by young women.
16:15One particularly damning clip from a 1992 party shows Trump and Epstein laughing and chatting,
16:21with Trump whispering something into Epstein's ear before the two share a knowing grin.
16:25A tape in the NBC archives of a Mar-a-Lago party shows Trump giving Epstein his personal attention.
16:33Donald! Donald! Donald!
16:35The footage, shot in November of 1992, before Trump opened the resort of the club,
16:41shows the future president surrounded by cheerleaders for the Buffalo Bills and Miami Dolphins.
16:47While Trump has since claimed they had a falling out,
16:50court records and testimony suggest their social circles overlapped for decades.
16:54In light of Epstein's arrest and subsequent death,
16:57the footage now plays more like an uncomfortable reminder of the company Trump was willing to keep and defend,
17:03until it became politically untenable.
17:06He said, quote, he's a lot of fun to be with, it's even said that he likes beautiful women as much as I do.
17:11And many of them are on the younger side.
17:13Which Trump moment on our list shocked you the most?
17:16Are there any prescient moments we missed?
17:18Be sure to let us know in the comments below.
17:20And Donald, as long as I have you here, it's pronounced huge, not huge.
17:25And here's another one, it's pronounced I am f***ing delusional, not I am running for president.
17:32I am f***ing delusional, not I am running for president.
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