What Trump’s 1987 book ‘The Art of the Deal’ reveals about 2024

“I like to be accommodating,” Donald Trump wrote in his 1987 mega-bestselling book, “The Art of the Deal.” “As long as they want to shoot, I’ll shovel.”

The context of the quote related to Trump’s work renovating Central Park’s Wollman Rink, where he was surprised that so many members of the media wanted to come and take pictures of him performatively shovel some cement onto the ice rink. But it’s also the perfect quote to describe so much of who Donald Trump is, and his sadomasochistic relationship with the media — full of pleasure and pain, love and hate.

It also exemplifies the fine line between perception and reality — Trump was not of course shoveling anything of substance, but if the press wanted to present it as if he was, he was happy to accommodate.

The mystique of Trump was on display in the 1980s as a young and successful real estate developer, just as it was as a reality TV host in the 2000s and a presidential candidate in the 2010s. There are important lessons to be gained from “The Art of the Deal,” as a playbook for what we should expect, and a peek behind the curtain about who Trump — the likely next GOP nominee and, if we believe the current polls, the next president — really is at his core.

I read “The Art of the Deal” in early 2016 during Trump’s first presidential run, back when few expected him to actually win even the nomination, and wrote about what I learned. There are new lessons, though, as we approach his latest bid, particularly with Trump’s multiple criminal trials coming in the year ahead.

But before we look ahead, it’s important to look back at the creation of the book, which was written in 1985-86, when Trump was just 38. It was cowritten — or, more accurately, ghostwritten — by journalist Tony Schwartz, who described the process as one largely built on observing Trump in business and personal settings and recasting what he heard and saw in Trump’s own voice.

Schwartz would later attempt to disown his role in the book and in helping to craft the Trump mythos as Trump rose to power in 2016. “I put lipstick on a pig,” he told the New Yorker. “I feel a deep sense of remorse that I contributed to presenting Trump in a way that brought him wider attention and made him more appealing than he is.”

Schwartz would go on to become a hashtag-Resistance talking head on cable news, and continues to ride the anti-Trump train to this day, speaking recently at the New Republic’s “Stop Trump Summit,” assuring the audience that he gave away the “blood money” he earned for the book to “causes he believes the former president would hate.” (So brave! I’m sure Trump is just devastated.)

But the book is crucial to explaining Trump’s massive success in business, in TV and later in politics. As he attempts to pull off a Grover Cleveland and win a second, nonconsecutive presidential term, remember these quotes — and the context.

One of the most well-known quotes is from page 58 in the paperback, in which Trump admits he plays “to people’s fantasies,” and drops a term that has explained quite a bit of his political acumen.

“A little hyperbole never hurts,” he wrote. “People want to believe that something is the biggest and the greatest and the most spectacular. I call it truthful hyperbole.”

“Truthful hyperbole” drove the media crazy in 2016 and has continued to infect the brains of those who hate him close to eight years later. It will grow in 2024, for one major reason. And it speaks to some other quotes from the 1987 book that now have added resonance.

“I fight when I feel I’m getting screwed, even if it’s costly and difficult and highly risky,” wrote Trump. And later: “I have an almost perverse attraction to complicated deals, partly because they tend to be more interesting.”

These quotes are about business deals, but now they relate directly to the four trials coming in 2024. They make two distinct but related points: Trump is going to fight these cases publicly, even if it’s costly both financially and potentially politically. But as a fan of “complicated deals,” could we see him cut a deal or two in the process?

If there’s a quote that exemplifies the sort of self-awareness that’s often missing from Trump’s public life, especially since the 2020 election, it’s this one from near the end of the book: “If there’s one thing I’ve learned about the rich, it’s that they have a very low threshold for even the mildest discomfort.”

Trump knows the rich — and more broadly the “elite” — in various settings now: the media, entertainment and now the D.C. “swamp.” If he is able to harness the knowledge gained in his first term, to press certain buttons he wasn’t aware of before, he might be able to overcome some of his blind spots and weaknesses. That’s a big if — he certainly didn’t seem to learn lessons in 2020 — but with the right focus, and right team around him, he could bring some extra “discomfort” to his opponents in 2024.

And we have to close with a quote that will drive the anti-Trump crowd crazy for its hypocrisy. “You can’t con people, at least not for long,” he wrote. “You can create excitement, you can do wonderful promotion, you can get all kinds of press, and you can throw in a little hyperbole. But if you don’t deliver the goods, people will eventually catch on.”

It’s “put up or shut up” time for Trump when it comes to various voting blocs — the #NeverTrump or at least DeSantis-leaners among the right, as well as the independents and suburban women that he won in 2016 but lost in 2020. But then there are other constituencies he appears to be gaining in polls now, overperforming among young Americans and Black men. But we have many months to go before November — will these groups, and others, “catch on” to a supposed “con” that Trump’s haters keep screaming about and hand Biden (or, perhaps, some other Dem who takes his place) a victory, or will Trump shock the world again?

Steve Krakauer, a NewsNation contributor, is the author of “Uncovered: How the Media Got Cozy with Power, Abandoned Its Principles, and Lost the People” and editor and host of the Fourth Watch newsletter and podcast.