Donald Trump has built a career on high-stakes risks and shattered norms, parlaying bankruptcies into a billionaire status and multiple scandals into two presidential terms. Now the former casino owner is doubling down on what may be his biggest gamble yet: restarting a war with Iran less than a month after signing a ceasefire he himself called essential to avert an economic crisis on par with the Great Depression.

Last week, Trump ordered renewed strikes on Iranian military and infrastructure targets, declaring the 17 June Memorandum of Understanding (MoU) signed at the Palace of Versailles dead in the water. Iran retaliated with drone and missile strikes on US Gulf allies. The MoU had drawn fire from neoconservative Republicans as a capitulation, but with midterm elections looming in November and Democrats eyeing both houses of Congress, stoking an unpopular war seems like electoral arson.

“There’s basically no timeline in which this makes any sense for preserving [Republicans’] midterm performance,” said Curt Mills of the American Conservative, calling it a “total loser” and evidence Trump doesn’t care about the midterms. Experts warn escalation could lead to a ground invasion and the “forever wars” Trump once condemned. Nate Swanson, a former State Department adviser, said the escalation has already exceeded his expectations, calling it a risky attempt to renegotiate the MoU that will likely fail.

At the heart of the conflict is the Strait of Hormuz, through which 20% of the world’s oil once flowed before the war began on 28 February. Iran closed the strait in response to US-Israeli attacks, sending oil prices soaring, and reopened it only under the MoU in exchange for sanctions relief. The MoU collapsed after Iran fired on commercial vessels using a lane near Oman instead of Iranian-controlled routes, which Washington calls illegal tolls. Some blame poor US negotiating; Vali Nasr of Johns Hopkins argues it was no misunderstanding but Trump’s intent all along, citing VP JD Vance’s hint that the MoU was a breather to replenish oil reserves and weaken Iran’s hand.

Both sides are gambling: Trump overestimates his military options; Iran overestimates its resilience. The absence of Iran specialists in the administration - Swanson says Secretary of State Marco Rubio “physically removed” key personnel - doesn’t help. Instead, Trump relies on Steve Witkoff, Jared Kushner, and Vance, a team that fundamentally misunderstands an adversary willing to suffer more than New York businessmen. Iran’s willingness to play the Hormuz card holds global energy hostage, potentially driving Trump toward a ground invasion. Regime change, sought initially with the assassination of Supreme Leader Ayatollah Ali Khamenei, is off the table for now; his week-long funeral aimed to re-establish unity. But with Iran retaliating against Gulf allies, a five- or 10-year conflict looms. Retired General Joseph Votel urges diplomacy and patience, warning the tit-for-tat could last weeks or months.