Art of the Con

Yesterday I heard one of Trump's advisors from his first administration talking about Trump's 'negotiations' with Putin on Ukraine, where he mentioned that Trump was following a strategy he outlined in his book, The Art of the Deal. I decided to investigate.

Back in the late '80s, a book hit the shelves that would change the course of history - not because it contained any great wisdom, but because enough people believed it did. The Art of the Deal was Donald Trump's first and most successful exercise in myth-making, a masterclass not in business but in self-promotion. It wasn't a business manual; it was a marketing gimmick. And like all great cons, it worked - spectacularly.

The book presents Trump as a brilliant dealmaker, the ultimate alpha negotiator who could bend the world to his will. It’s littered with tales of triumph, each one designed to reinforce the legend. But let’s set the record straight: it was all smoke and mirrors. His "deals" relied on inherited wealth, tax dodges, and political favours. His business career was a patchwork of bankruptcies, unpaid contractors, and lawsuits, but none of that made it into the book. What did make it in were pompous platitudes and half-baked business clichés - "Think big," "Maximise your options," "Protect the downside." A book stuffed full of grandiose nothings, masquerading as wisdom.

Here’s the irony: Trump didn’t even write it. That job fell to Tony Schwartz, a journalist who has since spent years publicly regretting his role in crafting the Trump myth. Schwartz has admitted that he fabricated much of Trump’s persona, piecing together something far more coherent and impressive than the erratic, attention-deficient blowhard he actually encountered. In his own words:

"I put lipstick on a pig."

But, thanks to the book’s success, the pig thought it was a prize-winning racehorse.

The so-called “business genius” spent decades peddling his self-image, conning his way into ever more disastrous ventures - Trump Airlines, Trump Casinos, Trump Vodka, Trump University, Trump Steaks, Trump Mortgage - each one a flaming wreck. None of this stopped people from swallowing the myth whole. When he ran for president, he did so on the back of this manufactured legend. Millions believed they were getting a savvy dealmaker who would “run the country like a business.” What they got was a serial failure with the temperament of a toddler and the financial acumen of a drunk gambler.

And let’s talk about those “business lessons” in the book. They’re either meaningless waffle or outright contradictory. Should you "go all in" or "keep your options open"? Should you "trust your instincts" or "know your market"? Should you "play tough" or "make friends"? No coherent strategy - just a buffet of soundbites, so you can pick whichever one fits your preferred delusion. The book’s main lesson? If you say something confidently enough, people will believe you - even if it’s bollocks.

And of course, Trump took his supposed deal-making skills to the White House, where they promptly crashed and burned. His approach to diplomacy - bullying, lying, and throwing tantrums - was a disaster. His “love letters” with Kim Jong-un led to nothing. His trade war with China backfired. His withdrawal from the Iran deal weakened U.S. influence. Even his NATO chest-thumping only alienated allies. The one thing The Art of the Deal got right? Trump is good at making a lot of noise while achieving very little.

Yet, even today, there are those who cling to the myth. They still believe he’s the shrewd, no-nonsense businessman who knows how to "get things done." In reality, he’s a bankrupt conman propped up by television and a ghostwriter. The Art of the Deal isn’t a business manual - it’s a historical artefact, a case study in the power of bluster over substance.

Schwartz himself has said that if he could rename the book, he’d call it The Sociopath. And frankly, that would be far more honest.