Trump: The Art of the Deal stayed atop the New York Times best-seller list for thirteen weeks in 1987. It contributed to making Donald Trump a household name. The book, which the author and publisher both later claimed Trump had nothing to do with writing, provides a guide for how Trump purportedly negotiates lucrative business deals.
Since President Trump nearly always frames both foreign and domestic policy in terms of “making a deal,” I was curious about how closely he follows his own advice, especially against the backdrop of the recent ceasefire with Iran. In the interest of full transparency, I did not waste time I could spend styling my hair reading Trump: The Art of the Deal. Instead, I used AI to summarize the primary negotiation themes.
Think Big
Trump’s first advice is not to settle for small deals, but to go for the big ones. In joining Israel and launching an attack on Iran, Trump was thinking big – maybe too big. Clearly, the President believed that the Israeli-U.S. offensive could pound the Iranians into submission in short order. The fact that the Iranians haven’t folded is the main source of his obvious frustration.
Mastering Negotiation
According to Trump, everything is negotiable. One must leverage power, know when to walk away, and use timing and pressure strategically. The leverage in the Iran war, of course, was the power and might of the U.S. military. However, Trump failed to recognize the leverage that could be exercised by Iran, not militarily but economically. The closing of the Strait of Hormuz and attacks on oil-rich U.S. allies in the region sent gas prices soaring and Trump’s approval ratings plummeting.
Trump either didn’t consider the timing or miscalculated it. His approval ratings were already falling, and losing control of the House during the upcoming midterms seems to be a forgone conclusion. With the unpopularity of the war and Trump’s erratic behavior, the U.S. Senate is now in play. Other than attacking at the conclusion of Ramadan, there appears to be no strategic reason for the timing of the attack, which lends credibility to the claim that Trump was pushed into the war by Netanyahu.
Create Leverage
Next, The Art of the Deal advises creating leverage. This must be what Trump was attempting when he posted, “Open the Fuckin’ Strait, you crazy bastards, or you’ll be living in Hell…” on Easter Sunday, and again a few days later, “A whole civilization will die tonight, never to be brought back again.”
Some will argue that the threats, as unhinged as they were, forced Iran to agree to a ceasefire. However, an alternate view is that Trump showed just how desperate he is to bring the war to an end and to stabilize gas prices and the stock market. Not to mention that the ceasefire at the time I am writing seems to only be for the United States, since both Iran and Israel fired on targets not long after the deal was announced.
The Power of Branding
In the book, Trump is referencing his personal brand from his eponymous structures to the gold trimmings. So far, the administration has been unable to effectively brand this conflict. Is it about nukes, regime change, oil, supporting our ally Israel, or something else? Consequently, it’s “Trump’s War,” which is probably not what he had in mind.
Be Flexible, Not Rigid
Perhaps this is where Trump aligns most closely with his own advice. As with most major initiatives and crises in his two administrations, everything is fluid all the time. The unpredictability might be an advantage in a real estate deal, but with foreign powers, the stock markets, and the American public, uncertainty is an albatross. Since the beginning of the conflict with Iran, the stock market has been volatile, and Americans have been uneasy. Our allies were not consulted in the least before the attack, then excoriated by Trump for refusing to take back control of the Strait of Hormuz.
Use Publicity to Your Advantage
Trump asserts that even controversial publicity can help to close a big deal. Maybe so, but the war’s publicity, including the death of 13 service members and the wounding of 380, has not resulted in citizens rallying to the cause. It is hard to see how publicity surrounding the administration’s wavering on the purpose of the war and subsequent testimony from Director of National Intelligence Tulsi Gabbard that Iran was not rebuilding its nuclear program moves Trump closer to a favorable deal.
Conclusion
While no stranger to controversy, in 1987, when Trump: The Art of the Deal was published, he had not yet filed any of his six bankruptcies. Following his casino failures, there was Trump Mortgage, GoTrump, Trump Vodka, Trump Steaks, Trump University, Trump Magazine, TrumpNet, Trump Serta Mattresses, and Trump Tower Tampa, which all flopped. Trump’s history points to modest successes (modest by billionaire standards), later fueling risky ventures and bad decisions.
In the realm of modern warfare, Trump is repeating the pattern. A precise and impressive mission in Venezuela stoked his belief that the U.S. military could subdue Iran expeditiously. Unlike overestimating the favorability of a business venture, missing the mark on war costs lives, billions of taxpayer dollars, and our reputation abroad.

