The Art of the Deal: How Trump's Foreign Policy Reflects His Business Background. Has America First Has Left Us Behind?
By: Saxton Sylvester
Long before he held public office, Donald Trump told the world who he was: a dealmaker. His 1987 book The Art of the Deal, co-written with journalist Tony Schwartz, laid out a worldview built on thinking big, negotiating from a position of maximum strength, and treating every interaction as a contest to be won. When he entered politics, he did not leave that worldview behind, campaigning on the claim that American foreign policy had become "a complete disaster" and that the country's allies were not "paying their fair share" in all three of his elections — language lifted directly from a businessman's ledger.
Trump's foreign policy can be best understood as the application of three core business instincts: the aggressive opening bid, the balance-sheet view of national interest, and a relentless talent for branding. These instincts produce pretty headline victories. But the deeper, unseen result here is that, taken together, the America First approach has left the United States in a weaker position than it occupied before. The ‘win v. lose’ tactics that close real-estate deals are mismatched to a domain that runs on continuity and trust.
The Opening Bid: Extreme Demands, Then a Narrowed "Win"
The most recognizable signature of Trump's negotiating style comes straight from his book The Art of the Deal. The method is to open with demands far beyond what is realistic, force the other side into a reaction, and then narrow those demands while declaring victory. Analysts repeatedly trace this pattern to his book, where he claimed, “I aim very high, and then I just keep pushing and pushing to get what I’m after. Sometimes I settle for less than I sought, but in most cases I still end up with what I want.”
Tariffs are the clearest example. Over the course of his second term, Trump transformed tariffs into a routine economic weapon. A lever for trade concessions, federal revenue, and political punishment all at once. The pattern follows the book: announce sweeping, shocking duties, wait for markets and counterparts to recoil, then settle into "deals" that leave tariff levels higher than where they started while claiming a triumph.
Whether this constitutes strategy or improvisation is genuinely contested, and that debate is worth airing. Skeptics coined the label "TACO", or "Trump Always Chickens Out" to describe a pattern of loud threats followed by retreat once markets punish him. Defenders, including analysts at the Institute of Geoeconomics, counter that this reading mistakes the opening threat for the real policy; in their view, the extreme demand is merely a starting bid, and judging Trump by his climbdowns misses the negotiating logic entirely. The same dynamic appeared with Iran, where maximum-pressure threats and military strikes gave way to a narrow, time-limited ceasefire. Nonetheless, the theme is the same for Trump whether it be buying a New York skyscraper or bombing Iran.
The Balance Sheet: Foreign Policy as Profit and Loss
As any good accountant would, a businessman reads the world as a set of accounts. Relationships are profitable or unprofitable; deficits are losses; partners are either paying their way or freeloading. Trump imports this framing wholesale into his international policy choices, and it shows up in three recurring habits.
First is the treatment of territory as an asset to be acquired. His floated proposals to buy Greenland and to reclaim the Panama Canal read less like grand strategy than like a developer eyeing undervalued property. Greenland in particular, as the Stimson Center has noted, became emblematic of broader strain across the transatlantic alliance. A reminder that treating sovereign relationships as real-estate opportunities carries diplomatic costs that do not appear on any balance sheet.
Second is the conversion of alliances into accounts receivable. Trump's demand that NATO members raise defense spending to five percent of GDP, and his insistence that continued American arms for Ukraine be financed by European governments, both recast mutual-defense commitments as invoices. Allies become clients who owe payment rather than partners bound by shared values.
Third is the reduction of diplomacy to line items. The administration restructured foreign aid into an "America First" fund while cutting deeply into global health and humanitarian programs. Read through the balance-sheet lens, soft power is essentially fake, an expense to be trimmed.
The Brand: Catchy Headlines and the Announcement as Product
Real estate is, at bottom, a branding business, and Trump has always understood that the announcement can be as valuable as the substance behind it. In foreign policy, this manifests as a gift for the memorable label and a tendency to make the headline deliverable.
The branding instinct is everywhere. His proposal to redevelop Gaza into what he called the "Riviera of the Middle East" packaged a contested plan in the language of a luxury development. When a ceasefire with Iran was reached, it was announced not through diplomatic channels but directly on social media, branded self-promotionally as a "double-sided" ceasefire. The product of the ceasefire for Trump was the proclamation.
The most revealing case is self-branding as a peacemaker. Trump's 2025 National Security Strategy asserted that his administration had "settled eight raging conflicts." The Stimson Center examined the claim and found it inaccurate: several of the eight were not actual conflicts, many remained unresolved, and Trump had played little to no role in those that did reach some resolution. This is branding outrunning substance, akin to a business keeping brand image above production.
Has It Worked? The Case That America First Has Left Us Behind
Overall, the collective evidence displays that this strategy has done more harm to the US than improvements. The strongest evidence that the approach has backfired is in the behavior of America's own allies. By early 2026, longtime partners had adopted a new watchword borrowed, fittingly, from the world of finance: "de-risking." Originally an investment term and later shorthand for reducing dependence on China, it was now being applied to the United States itself, as allies moved to insulate themselves from an unpredictable Washington.
That hedging produced concrete realignment. Over the same period, Canada and China agreed to reduce trade barriers, the United Kingdom moved to reset ties with Beijing, and the European Union advanced trade agreements with Mercosur and India. A wave of dealmaking that increasingly routed around the United States rather than through it. For a strategy premised on winning, the spectacle of the world's largest economy growing more isolated on trade is difficult to square with success.
Domestically, Trump's tariff weapon also has met resistance. In February 2026, the Supreme Court struck down Trump's sweeping tariffs on nearly all trading partners, knocking the legs out from under the central economic instrument of the America First agenda. And on the most consequential security question of the moment, a leaked 28-point blueprint for ending the war in Ukraine drew sharp criticism: Kyiv and its European partners warned that the document read less like an American peace offer than like a Russian roadmap for Ukraine's defeat, calling on Ukraine to cede territory, cap the size of its military, and renounce its NATO ambitions. A deal that hands an adversary its long-standing objectives is not, by any conventional measure, a win for the United States.
Where It Has Worked
As damning as this seems, there are arguments for the other side of this. A sympathetic analysis in Foreign Affairs credits Trump with achievements that eluded his predecessors. On burden-sharing, he extracted commitments from allies to raise defense spending substantially, and European contributions to Ukraine's defense rose under his insistence that the United States supply weapons only if Europe paid for them. By this accounting, the transactional approach did what decades of polite requests could not.
On great-power competition, another Foreign Affairs assessment argues that Trump's "art of the deal" instincts may be reviving direct diplomacy with China. His willingness to engage Xi Jinping personally and repeatedly, and the tendency of both capitals to compartmentalize their disputes rather than let any single disagreement spiral, is read by some as a return to disciplined great-power management. And the leverage school insists, once more, that the apparent retreats are deliberate. A high opening bid followed by a partial climbdown can still leave outcomes shifted in America's favor, as tariff levels that settled higher than their starting point arguably did. These are real arguments, and the defense rests on real outcomes: a five-percent NATO commitment, a larger European share of the Ukraine burden, a Gaza framework, and open channels with Beijing.
Costs over Gains
The decisive flaw in the business model is that it treats diplomacy as a one-off transaction when it is in fact a repeated game. A real-estate deal ends at the closing; the parties need never meet again, so squeezing every advantage costs nothing in the long run. International relations work the opposite way. The same governments face one another year after year, and absence of trust compounds. Every concession extracted by threat raises the price of the next negotiation, because counterparts learn to hedge and seek alternatives.
That is precisely what the evidence shows. The five-percent commitments and the Gaza framework are transactional and, by their nature, reversible. The erosion of trust is not. When allies begin "de-risking" from Washington and signing trade deals that exclude it, they are rewriting the rules of international engagement in ways that will outlast any single administration and orient global markets away from American suppliers. The opening-bid tactic wins the round but spends credibility; the balance-sheet view treats allies as vendors and is surprised when vendors shop elsewhere; the branding inflates victories — the "eight conflicts," the fragile ceasefires — that do not survive contact with reality.
One caveat strengthens rather than weakens this argument. It is fair to ask whether these patterns reflect Trump's business background specifically, or simply an America First ideology, or personal temperament. The honest answer is that the three overlap. But the business framing has unique explanatory power because Trump himself supplies it: he reaches for the vocabulary of deals, leverage, and balance sheets unprompted, and The Art of the Deal remains the text he points to. The instinct is not borrowed from a foreign-policy doctrine; it predates his politics by thirty years.
Conclusion
Return, finally, to the book. The instincts that built a real-estate brand, the audacious opening offer, the relentless focus on leverage, the genius for the memorable label, are not worthless in diplomacy. They have produced genuine, if reversible, gains. But they are fundamentally mismatched to an area whose value lies in continuity and whose dividends are paid in trust. The deals may close. The relationships do not survive the closing. And in foreign policy, it is the relationships that determine whether a nation ends up ahead or behind.
References
Capistrano, A. (2026, April 15). Donald Trump, "The art of the deal" and the "TACO" myth. Institute of Geoeconomics. https://instituteofgeoeconomics.org/en/research/2026041502/
Center for American Progress entry — see McManus & Le below.
Collinson, S. (2025, April 24). Analysis: "The art of the deal" meets global reality. CNN. https://www.cnn.com/2025/04/24/politics/trump-art-of-the-deal-china-tariffs-russia-ukraine/index.html
Council on Foreign Relations. (2026, February 23). Trump's 2026 State of the Union: Foreign policy issue guide. https://www.cfr.org/articles/trumps-2026-state-of-the-union-foreign-policy-issue-guide
Kempe, F. (2026, January 5). The most significant question for Trump's America in 2026: What sticks? Atlantic Council. https://www.atlanticcouncil.org/content-series/inflection-points/the-most-significant-question-for-trumps-america-in-2026-what-sticks/
McManus, A., & Le, D. (2026, February 19). How Trump's unilateral foreign policy has eroded American power. Center for American Progress. https://www.americanprogress.org/article/how-trumps-unilateral-foreign-policy-has-eroded-american-power/
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