What Trump’s Campaign Is Taking From 2016 and 2020

Julia Press
·17 min read
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Team Trump is up against historic criminal trials and a failed reelection bid in 2020. Despite this, his 2024 campaign is organized, frugal – and getting results.

On today’s Big Take podcast, DC host Saleha Mohsin takes stock of the 2024 Trump campaign through the lens of his past two runs, speaking with former White House communications director Anthony Scaramucci and Bloomberg politics reporter Nancy Cook.

Listen to the Big Take DC podcast every week.

Here is a lightly edited transcript of the conversation:

Saleha Mohsin: When Anthony Scaramucci joined Donald Trump’s 2016 presidential campaign, he said even insiders thought it was a longshot.

Anthony Scaramucci: Nobody on that campaign thought that Donald Trump was gonna win. Nobody.

Mohsin: Unlike most politicians, Trump had fiery rhetoric. But it worked for him. And his unpredictable approach foreshadowed what was to come from his administration. It was no surprise that the man who’s known for saying “you’re fired” was quick to turnover his staff while on the trail, and when he eventually won the White House. Trump fired Scaramucci after 11 days as communications director.

Scaramucci: Listen it was chaotic.

Mohsin: But that was then. It’s 2024. Trump has new challenges in front of him as his latest presidential bid comes into focus. And his old campaign playbook — which was basically a lack of a playbook — has gotten some updates.

Scaramucci: He's not raising the money, uh, that he was once raising. Joe Biden is eclipsing him on the money. But he is well established now. He has a more disciplined campaign and they have him on message and they have him disciplined. It's a better campaign.

Mohsin: But just how does Trump’s 2024 campaign strategy compare to his previous ones? And will those changes be enough to win over an electorate that didn’t vote to keep him in the Oval Office in 2020?

Today on the show, with Donald Trump on trial in Manhattan, and the likes of his former lawyer Michael Cohen testifying, all eyes are on how the former president is campaigning through it. We take stock of Trump’s 2024 strategy through the lens of his past two runs. I speak with former White House communications director Anthony Scaramucci, along with Bloomberg reporter Nancy Cook, who’s followed Trump since the moment he descended the Trump Tower escalator and announced a bid for the presidency in 2015.

From Bloomberg’s Washington bureau, this is the Big Take DC podcast. I’m your host Saleha Mohsin.

When Trump launched his very first presidential bid, he was the first to do so with no previous public service experience, although he’d flirted with the idea for decades.

That’s part of the reason people didn’t take the reality TV host and businessman seriously when he announced his intent to run for president back in 2015. But those experiences shaped his approach to politics.

Nancy Cook: So the Trump campaign in 2015 was super chaotic. And he really ran this presidential campaign almost like a family business.

Mohsin: Nancy Cook is a politics reporter at Bloomberg.

Cook: There was like a tiny group of people around him. You had a bunch of different campaign managers. People were fired and then brought in. Corey Lewandowski was in charge, he got fired, Paul Manafort was in charge, he got fired, you know, he brought in Kellyanne Conway, there was just a ton of churn. And I remember very distinctly, I worked at Politico then, sitting in the Politico newsroom when the Access Hollywood story broke.

Bloomberg TV: A video obtained by the Washington Post features audio of Trump in 2005, making comments that the words lewd and vulgar are mild descriptions for… he was talking to Billy Bush from Access Hollywood—

Cook: and thinking, ‘oh wow, like, this is really gonna be the end for him.’

Bloomberg TV: Women are gonna come out in droves, and they're gonna speak, and that's wh— the election ended today.

Cook: And it wasn't. There were just so many moments like that where you thought, ‘Oh, wow, Republicans don't talk about trade this way.’ Or, ‘oh, wow, you know, he's saying all these insane things about immigrants and, you know, people aren't going to like that.’

Mohsin: All this turnover, and the bad headlines, sparked infighting amid team Trump. Remember: for most of the 2016 general election campaign, even most Republicans thought Trump would lose to Hillary Clinton. The polls were not in his favor. And Trump’s campaign wasn’t the first to become chaotic due to a bout of bad headlines and bad poll numbers.

Cook: My takeaway from that is that, you know, Trump really has had nine lives politically, but even more so, you know, he sort of always comes back again and manages to turn a lot of things that would be political disadvantages for other candidates into strengths.

Mohsin: Even before the Access Hollywood tape that many thought would sink Trump’s campaign, his divisive brand made it an uphill battle. Some traditional Republican donors shied away from his bid.

Cook: It wasn't well funded. It was kind of scrappy. They kind of had like, no battleground operation or strategy other than Trump's own instinct and his ability to like define his opponents very quickly and succinctly. Marco Rubio, who he's now considering for vice president, he named, you know, little Marco.

Mohsin: It’s a strategy that shocked Republican party fixtures like Mitt Romney.

Mitt Romney - Bloomberg TV: This has been a low road campaign pretty much from the beginning.

Mohsin: That’s Romney, speaking on Bloomberg TV in March of 2016.

Cook: He dispatched with Jeb Bush, who a lot of people thought was going to be the Republican nominee. You know, all the top political reporters that I know in Washington were put on the Jeb Bush campaign.

Scaramucci: If Jeb was running in the mid ‘90s, he would have been an exceptional presidential candidate. Bush was more organized, he had more money than Donald Trump.

Mohsin: Anthony Scaramucci, an investment banker, was working on the Jeb Bush campaign’s finance committee at the time.

Scaramucci: But he lost that campaign because the election was in 2016, and the electorate had shifted.

Cook: Trump dispatched with him, you know, low energy Jeb.

Trump - Bloomberg TV: He is a low energy person by nature and that's okay. There's nothing wrong with that.

Mohsin: Trump took the Republican primary nomination, winning over disillusioned voters and people who wanted a change. Someone outside the political establishment.

His campaign rhetoric was uniquely bombastic. Instead of advocating for immigration reform, he led chants to “build a wall.”

AP: build a wall… [chant]

Mohsin: And it stuck. Emerging as the Republican frontrunner, he brought more establishment party members into the fold. People like Scaramucci.

Scaramucci: Donald Trump recruited me into that campaign when Bush got knocked out of the campaign by Donald Trump. And I made a decision to work for him. I thought it was the right, loyal thing to do as a member of the Republican Party, member of the Republican establishment. So I went to go work for Mr. Trump. It was messy.

Mohsin: Were there moments where you just thought, ‘how on earth are we ever going to get elected if we can't get our campaign organized?’

Scaramucci: Nobody on that campaign thought that Donald Trump was gonna win. Nobody. Steve Bannon didn't think he was going to win. Jared Kushner. Nobody thought he was going to win that election.

Donald Trump didn't think he was gonna win. On the evening of the election, he was preparing himself to take a trip to Scotland to play golf. He wanted to be out of the media spotlight when Hillary Clinton was accepting the win of the presidency.

Mohsin: Where were you on election night?

Scaramucci: I was with him. I was sitting on a couch with Rudolph Giuliani, at 10:15 at night, and Mayor Giuliani turned to me, and said, ‘I know the state of Florida very well. I have a home in the state of Florida. Those precincts that have yet to post their results, those precincts are voting for Trump. He's going to win the state of Florida. He's going to win this election.’

Mohsin: And how did Trump seem?

Scaramucci: Trump was about as serious as I've seen him in the 20 years that I've known him. He was sober. He was serious. He was nervous.

Mohsin: That disorganization… it came to define his presidency, too. But when it came time for reelection in 2020, his team took a new approach. Here’s Nancy Cook again.

Cook: In 2020, I was covering the Trump White House and his campaign tried to be 100 percent different than 2015. They tried to be super professional. They had raised a bunch of money. Unlike 2015, where it was sort of a ragtag, you know, family run business kind of vibe, and, and sort of a small group of staff around, there was a huge amount of staff. They had org charts and, you know, a communications team and a campaign manager.

Their problem was that they were well funded, but they really misspent a lot of money. They blew a lot of money on fancy office space, you know, on a huge staff. And they got to the point where they did not have money for advertising at some key points.

And you have to remember too, I mean, when I was covering the Trump White House, the economy was doing well. You know, I really thought Trump was going to sail to re-election. And then COVID hit, and I would say that really just changed the whole trajectory of the election because Americans were really disappointed by the way Trump handled it. And they really, you know, wanted a different type of leadership then.

Mohsin: Leading up to the election, many people lost their jobs, lost family or friends, and on top of it all, America was rattled by a reckoning over racial injustice. It was enough to cost Trump the election.

In the time since, the people around him have taken stock of what went wrong. And it’s informing some of his 2024 campaign.

Cook: It's lean and mean, sort of like 2015, but I guess the difference is, is that they are very skilled and very organized and they know what they're doing.

Mohsin: Coming up: who’s behind the current campaign, how they’re leveraging Trump’s legal challenges, and what could pull it apart.

Trump’s 2024 campaign is trying to merge the most effective elements of his past two runs.

Like Bloomberg’s Nancy Cook said, it’s lean like 2016—with a pared down staff and tight budget. But it’s also more professional, like in 2020.

Cook: So there's really two people running it. His campaign manager is this woman, Susie Wiles, who is a longtime Florida operative. And really, like, has helped turn Florida red, like, to a reliably red state. She's been involved in Republican politics for decades, has, like, very deep ties throughout Florida. She's a woman of few words. She does not try to impose her view on Trump. She presents him with options, she does not like to spend money. She's frugal. She's organized. She's militant.

And then there's another key person, Chris LaCivita, who is a long time Republican operative who comes out of Virginia. He was in charge of the whole primary strategy, which Trump won quite handily, and then he has been really focused on the battleground stuff, and he's helped them sort of merge the campaign and the Republican National Committee.

Mohsin: Nancy says, Wiles and LaCivita have harnessed Trump’s personality as part of their campaign strategy. Giving him space to use it where it helps them, without leaving much room for the infighting among Trump’s official and unofficial advisers which, in the past, has led to firings and chaos.

We spoke about this with Danielle Alvarez, a senior advisor for communications on the Trump campaign.

Danielle Alvarez: We're taking our lead from the president. He, uh, ultimately dictates our cadence and he has a massive movement behind him. And so what we're focused on doing is harnessing that energy.

Mohsin: While campaign operations are running smoother than in 2016 and 2020, Trump is still Trump – his rhetoric remains bombastic, just the way his supporters like it.

Cook: I don't think that they have tried to change Trump at all. You know, he is still out there doing his thing. I think that what they have done successfully is put sort of a small team around him, and there's still sort of actors in the Trump orbit who are sort of floating around, who call Trump and talk to him or show up at Mar a Lago. They're not trying to sort of keep those people out, they just sort of redirect them. They don't let those people get involved in the real campaign organization.

Mohsin: You could see their strategy in action during this winter’s primaries.

Cook: Traditionally in politics, it's like candidates spend, you know months and months on like a year courting Iowa voters. Ron DeSantis visited, like, all of the 99 counties in Iowa and, like, had a million town halls and meet and greets and Nikki Haley was in Iowa and South Carolina. Trump did none of that.

Mohsin: Instead, team Trump was focused about where and how they spent resources.

Cook: Trump basically, showed up, like, three days before each of these states primaries or caucuses. Would hold a few rallies. He had a bunch of surrogates who would also come into the state with him. It was like MAGA world would land in Iowa four days before the primary. Make a big splash. Trump would hold like two rallies and then he would completely dominate the primary.

He just came in at the end and like, made a real heavy push. To me, just watching that unfold and covering that in these different states was really emblematic, like, ‘man, these people are organized, and they have a different strategy, and, and they really kind of, like, broke the way people traditionally do primaries.’

Mohsin: Trump’s legal issues mean that being nimble is crucial to his success. He can't really run a traditional campaign—spending his time on the road, holding rallies and shaking voters’ hands. Trump's been stuck in a Manhattan courtroom almost every day for weeks, and there are no cameras or recorders allowed inside. But team Trump has managed to turn even that into an advantage.

Cook: They have been thinking about how to merge a political and campaign strategy since the fall. And they have been thinking about basically how to make the courtroom as much kind of like a rally or a political event as possible. So like, he comes out and says something in the morning…

Mohsin: Here he is on Monday, speaking outside a Manhattan courthouse.

Trump - AP: The New York Times just came out with a poll that shows us leading everywhere by a lot…

Cook: He comes out and says something in the evening. They've done a few little, you know, stops in Manhattan where he's, you know, brought pizza to firefighters or he visited a bodega in upper Manhattan.

Bloomberg Quicktake: Everything good? Four more years… [fade]

Mohsin: Another day, he visited a construction site and signed red “make unions great again” hats before going into court. He was met with cheers.

Bloomberg Quicktake: [cheers]

Cook: And so they have done these things to try to use it to his political advantage.

Mohsin: And maybe it's easier to contain a campaign that's just in one place rather than rallies and, and moving around the country and then different people having access to him.

Cook: I think even if he didn't have this they wouldn't be having rallies all the time. You know, the rallies are expensive, you know there's I don't think they see any point in him doing rallies like every day now. Even when he's done with the court case in New York, I don't think we're going to see him doing like wall to wall campaigning this summer or wall to wall advertisings.

Mohsin: The Trump campaign told us that they’re trying to hold rallies and events on days when he doesn’t have to be in court.

Meanwhile, a seat at the Trump trial has become the hottest ticket in town. That’s according to Robert Samuel, who was outside the courthouse on Tuesday.

Robert Samuel: I'm a professional line sitter. Most of the times we're waiting for Cronuts and Broadway shows. Uh, but I will say to Donald Trump's credit, he is a jobs creator. We've been out here every day.

Mohsin: Samuel’s company, Same Ole Line Dudes, charges by the hour. He wouldn’t reveal exactly what time he showed up to secure the coveted first and second place spots, but Miliana Villalona says that she arrived at 5.

Julia Press: 5 p.m.?

Miliana Villalona: No, a.m. So over like 24 hours.

Mohsin: Around 8:30 in the morning on Tuesday, Villalona was handed one of the green tickets that meant she’d make it inside—not the actual courtroom, but the overflow viewing area. That’s when she heard someone else offer up his ticket for $400.

Villalona: Then I stopped it. And I said, ‘I'll give you, you can have mines for 350.’

Mohsin: Sold. To her, it was a fair price.

Villalona: It definitely was. As a college student, 18 years old. Yes, it was. That's money I make in like a week.

Mohsin: There’s a lot of time between now and election day. And Nancy says, what happens in the meantime could determine the fate of the campaign.

Cook: I think what I'm curious about is, can they keep this lean, mean operation that's not fighting with each other, you know, intact, uh, and then what happens when the polling is bad?

Mohsin: Current polls are showing Trump outperforming Biden in most swing states. But public opinion is volatile. At some point in the next five months, those polls may change.

Cook: There will be some moment where, like, things will go poorly with Trump or Biden will be up in the polls and Trump will be down and, like, Trump's not going to take the blame for that. So does he turn on these people who have run his campaign successfully so far? Maybe. I mean, that's what we've seen him do in the past in the White House with other campaigns.

Mohsin: Nancy told me that in her chats with Democratic operatives, it seems that even Trump’s opposition is aware that it would take some unanticipated event to turn polls, and the narrative, against Trump and give Biden a better shot.

If the Trump campaign runs out of cash, or he faces jail time for being in contempt of court, 2024 could get complicated for his tightship campaign. People like Anthony Scaramucci, who once backed him unequivocally, now denounce him. And he could risk losing even more allies if he takes his “you’re fired” approach to his 2024 staff.

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