Why Trump’s 'art of the deal' fails in war

Lee Hyun-sang
The author is a columnist at the JoongAng Ilbo.
The United States' war against Iran is sinking deeper into a quagmire. Washington, shaken by the economic shock, is searching for an exit but cannot find one easily. In just the first six days of the war, the cost reached $11.3 billion, or about 17 trillion won. That works out to nearly 33 million won every second. The Pentagon has asked for an emergency supplemental budget of $200 billion. The scenario Washington initially touted — a short campaign of precise strikes — has vanished.

At the base of this war lies President Donald Trump's trademark "art of the deal," a phrase associated with "The Art of the Deal" (1987). His method is clear: drive the other side to the extreme, generate fear, then force through the terms he wants. Its core elements are to overwhelm the opponent by thinking big, maximize unpredictability by widening options and seize the opponent's weak point through leverage. At the start of the war, the United States seemed to dominate the board by wiping out key figures in Iran's leadership.
But war has not moved according to Trump's calculations. He now appears trapped by the Strait of Hormuz and November's midterm elections. His repeated bluster, TACO-style retreats — a term used by critics to describe his tendency to make threats and then pull back at the last moment ("Trump Always Chickens Out") — and wavering moves have deepened doubts about his judgment.

Why does a method that worked in business reveal such sharp limits on the diplomatic stage? Business ends with a contract, but diplomacy is a more tangled process in which national interests, political legitimacy and domestic calculations are intertwined. At its core, Trump's style seeks immediate advantage in zero-sum fashion. Diplomatic negotiation, by contrast, aims for a plus-sum outcome that recognizes the other side's existence and seeks to avoid catastrophe. Even war is no exception. Carl von Clausewitz wrote that war is the continuation of politics by other means. By moving first to eliminate Iran's leadership, Trump may have made negotiation harder. Behind such decisions stands Israeli Prime Minister Benjamin Netanyahu, who has strong incentives to prolong the war and thereby extend his political life.
The second reason is that the parties to a deal are different. In business, two chief executives can sign and finish the matter. In politics, however, countless outsiders — voters, public opinion, allies and international organizations — hold the power to determine success or failure. U.S. allies, worn down by Trump's unilateralism, have responded coolly, saying in effect that this is not their war. The problem returns to domestic politics. Trump seems to have taken too lightly the fact that most U.S. allies are democracies sensitive to public opinion.
A third factor is emotion, a variable that cannot be neatly calculated. Trump seems to have assumed that removing Iran's leadership would make victory easy. That was a misjudgment. In medieval European warfare, there was an unwritten rule that kings did not kill kings. The point was to leave an opposing side in place for negotiation. Rulers wished to avoid vengeance, uncontrolled escalation and the blurring of war's purpose. Trump's business instinct appears to have left no room for the pride of Iran, a regional power with a long imperial memory. The simple grammar of business does not work on the battlefield.

Even Trump's base inside the United States, the isolationist MAGA camp, is beginning to waver. These supporters backed him partly because they felt they had been losers in globalization. But they are losing patience as Trump's decisions begin to threaten their interests. To borrow the logic recently used by commentator Rhyu Si-min, who stirred controversy in Korea by dividing a political support base into A, B and C groups, the greatest dissatisfaction now appears to be growing not among value-driven core loyalists (A) but am...