OPINION: The art of losing
Published 1:30 pm Sunday, May 31, 2026
Donald Trump spent years selling himself as a master dealmaker, but his chaotic handling of the Iran crisis revealed something far more dangerous: a president so addicted to bluff, escalation, and performance that he cannot recognize when the hand he is playing has already lost.
The clearest measure of that failure emerged when details of Trump’s proposed Iran agreement began surfacing on May 23 and May 24. After spending years denouncing Barack Obama’s nuclear deal as weak and humiliating, Trump now appeared willing to accept a framework even less restrictive than the agreement he destroyed.
Reports indicated the proposed deal would restore access through the Strait of Hormuz, ease sanctions, release frozen Iranian assets (subject to Iran surrendering it uranium stockpile), and postpone major disputes over nuclear enrichment into future talks. Unlike Obama’s agreement, which imposed tighter inspection structures and clearer enrichment limitations, Trump’s emerging framework reportedly allowed limited Iranian nuclear activity under temporary restraints while core disputes remained unresolved.
Trump had promised maximum pressure and total capitulation. Instead, he appeared headed toward a face-saving compromise crafted to contain a crisis his own policies had intensified.
Then came May 25.
Even as administration officials described diplomacy as imminent, U.S. forces launched what the Pentagon called “defensive” strikes against Iranian missile positions and mine-laying vessels near the Strait of Hormuz. Trump had moved from announcing peace to authorizing new bombing runs in less than two days.
That is not strategic mastery. It is geopolitical improvisation bordering on incoherence.
The deeper problem is that the pattern is entirely familiar. Long before politics, Trump built his image through spectacle, exaggeration, and chaos marketed as confidence. His casinos entered bankruptcy. His resorts collapsed under debt. Investors and creditors absorbed losses while Trump protected licensing deals and branding rights. Failure was rarely admitted. It was repackaged as brilliance.
War, however, is less forgiving than corporate restructuring.
Trump spent years condemning Obama’s Iran agreement as capitulation. He withdrew from it promising tougher sanctions, stronger leverage, and total Iranian compliance. Instead, Iran expanded uranium enrichment, regional tensions intensified, global shipping destabilized, and the United States drifted toward another Middle East conflict with no clear objective or exit strategy.
Words cannot substitute for planning.
A serious commander defines objectives, builds alliances, measures risks, and prepares for consequences before missiles fly. Trump prefers impulse over discipline, grievance over judgment, spectacle over strategy. Those instincts may dominate a news cycle, but they are catastrophic foundations for serious statesmanship.
His defenders portray unpredictability as strength. In reality, unpredictability becomes weakness when allies stop trusting you and adversaries stop fearing you. A bluff works only if others believe the player understands the game. Trump increasingly resembles a gambler pushing more chips onto the table because he cannot admit the cards are bad.
The economic consequences are already spreading beyond the Gulf. Disruptions around the Strait of Hormuz have rattled energy markets and pushed oil prices upward. Americans experience those costs quickly and relentlessly. Americans are seeing gasoline prices rise, and airline fares climb. Shipping costs are spreading through supply chains and into grocery stores. Inflation is returning, carrying the invoice for military escalation.
This is how foreign policy failure reaches the family dinner table.
The political damage compounds alongside the economy. Recent observations indicate swing-district Republicans may be growing nervous as voters confront higher prices and deeper instability tied to another Middle East conflict with no visible endpoint.
Trump’s history makes this deterioration easier to recognize. Again and again, he has confused leverage with noise, confidence with competence, branding with substance. He sold bankrupt casinos as triumphs. He marketed debt-fueled excess as brilliance.
The same instincts now shape American foreign policy.
He destroyed one Iran agreement, drifted toward a weaker replacement, signaled concessions on May 23 and May 24, then ordered new bombing strikes on May 25 when the contradictions collapsed under their own weight.
He cannot manufacture chaos and then market himself as the cure.
The central danger of Donald Trump has never been ideology. It has been incapacity: a lifelong habit of substituting swagger for strategy and performance for substance. A leader who cannot recognize a losing hand eventually gambles with other people’s security and other people’s lives.
And that is where the Iran crisis leaves the United States: trapped between escalation and retreat while a president who built his career selling the illusion of winning still cannot admit that the hand he is playing was lost long ago.
Van Abbott is a 36-year resident of Alaska having worked in Ketchikan, Fairbanks and Anchorage as a municipal, financial and utility manager. He resides in Ketchikan and is currently a freelance writer. He served as a Peace Corps teacher in the 1960s. See his website: politicalwinds.org.
