• United Nations
• Geopolitics
• United States

September 22, 2025, 11:43 AM View Comments ()

When it comes to international conflict, U.S. President Donald Trump learns everything the hard way. On issue after issue—North Korea, Venezuela, Ukraine, Gaza, and more—Trump begins by bucking conventional wisdom and insisting that a bold new approach will yield breakthroughs. Implied, and often said outright, is that past officials who worked on the matter were feeble, inept, and craven. Trump insists that his determination and powers of persuasion will force seismic change—cowing enemies, bridging schisms, and achieving diplomatic masterstrokes.

Yet time and again, after gambles and gambits, Trump comes to the same conclusion: While he might not admit it, his approach reverts to something much closer to what policy wonks and advisors urged on him at the outset. Trump’s overconfidence and distrust of expertise drive time-consuming, costly, and sometimes embarrassing detours up clearly marked dead ends—which we may see again at his speech at the United Nations General Assembly on Tuesday. By recognizing this flash-to-fizzle arc, advocates, policymakers, and U.S. allies can work more effectively to exert their influence on the administration and push Trump more quickly up his learning curve.

This pattern has been evident since Trump’s first term. In 2017, he threatened “fire and fury” in response to North Korea’s escalating missile tests. He toughened sanctions on Pyongyang, pressed Beijing to use its leverage, and sought a face-to-face meeting with Kim Jong Un, preconditions be damned. Trump’s Singapore summit with Kim in June 2018 culminated in an airy declaration on denuclearization and peace. Yet a second summit the following year ended in deadlock, and a follow-up at the Korean Demilitarized Zone yielded nothing. Trump then defaulted to the grinding approach long advocated by experts: deterrence, isolation through sanctions, and reliance on pressure from regional allies. Bold talk of denuclearization faded.

Similar patterns occurred elsewhere in his first term. On Venezuela, Trump threatened military intervention to topple strongman Nicolás Maduro. He also urged Latin American allies to join a maximum pressure campaign and floated direct talks with Maduro. When progress proved unavailing, Trump resigned himself to disengagement and low-stakes pressure tactics resembling those of former President Barack Obama. (Eight years later, Trump is again ratcheting up pressure by blowing up Venezuelan vessels that the administration claims were carrying drugs to the United States. Yet while the moves are aggressive and legally dubious, there is no sign for now that Trump has the will to follow through on an attempt at regime change.)

On Afghanistan, after campaigning to end “forever wars” and musing on an abrupt withdrawal, Trump authorized secret talks with the Taliban and even floated the idea of inviting the group’s leadership to Camp David. When dialogue on a transformational truce faltered, Trump turned to a conditional withdrawal framework along lines that security and diplomatic experts had discussed for years.

On Iran, Trump disavowed Obama’s nuclear deal and swore to win more favorable terms. But talk of summits and grand bargains went nowhere, leading the Trump administration to set the clock back to a conventional, pre-Obama approach focused on containment and sanctions. On Cuba, Trump declared that he would roll back Obama’s opening in search of a “better deal.” Instead, relations froze, and the decades-old containment strategy sprung back to life.

The arc of craving a high-profile “deal” and then, when the moonshot falls short, losing interest and reverting to foreign policy-as-usual is back with a vengeance in Trump’s second term. During his 2024 campaign, Trump vowed to end the war in Ukraine “within 24 hours” of entering office, decrying the supposed incompetence of the Biden administration. In February, Trump touted a phone call with Russian President Vladimir Putin and claimed that peace talks would soon convene. Trump then shocked U.S. allies by publicly berating Ukrainian President Volodymyr Zelensky and pausing intelligence and military cooperation with a beleaguered Kyiv.

As talks stalled and Russia’s missile attacks intensified, Trump reluctantly backed off claims of a unique bond with Putin. His high-profile summit with the Russian leader in Alaska last month failed to achieve much, and now, the United States and Europe are back to focusing on how to strengthen Ukraine’s hand through military assistance.

Trump’s engagement on the Israel-Hamas war has differed in a key respect, in that he has not entered into talks himself. Instead, in February, he dropped a bombshell from the White House, proposing to turn the enclave into “the Riviera of the Middle East.” The grandiose idea, which would force Jordan and Egypt to accept the relocation of Palestinians, was a nonstarter roundly judged as unworkable, illegal, and offensive. Now, the Trump administration is back to the drawing board here, too.

In late August, Trump reportedly met with his son-in-law, Jared Kushner, an architect of Middle East policy during his first term, and former U.K. Prime Minister Tony Blair to discuss Gaza’s postwar governance—a matter cited by experts for years as an essential yet painstaking predicate to ending the war. Since then, Trump has adopted a passive posture, with Secretary of State Marco Rubio conceding last week what the Biden administration confronted over 15 months of vigorous effort: namely, that the war in Gaza may have no path to diplomatic resolution.

It may be tempting to dismiss Trump’s high-wire acts as doomed spectacles and then passively wait for him to adopt more conventional approaches. But those seeking to influence the administration need to shape their own strategies in light of Trump’s tendencies.

In foreign affairs, at least, vociferous pushback from foreign capitals, experts, and the media has been crucial in steering Trump away from many of his ill-conceived lurches. Examples include the furious uproar over Trump’s vision for Gaza, the derision over his designs on the Panama Canal, and the overnight démarche of European leaders to the White House on the heels of the Alaska summit. Strong reactions to Trump’s flights of fancy can push him to revert to convention—which, while not always desirable, is often better than his pipe dreams.

Meanwhile, traditional cautionary voices seem to have little power to deter Trump. He is prone to dismiss counsel from experts as timid, self-interested, or unappreciative of his unique prowess. Trump has little patience for preparation or policy intricacies, preferring personality-driven improvision. Because of that, the hemorrhaging of expertise in Washington due to personnel cuts at the National Security Council, State Department, and intelligence agencies—and the assignment of officials such as Rubio to two or more roles—may matter less than they ordinarily would; Trump would likely not have listened to the departed officials anyway.

Given Trump’s tendency to dismiss any argument or lesson he has not arrived at himself, the question becomes how to accelerate his learning curve before grave damage is done. He had to personally confront Kim’s and Putin’s intransigent styles—even though they are well-documented—to accept that he could not simply overcome them. Normally, summits serve as a culmination of extended diplomatic efforts to secure agreements. For this White House, in contrast, they may be a necessary stage in the president’s own experiential foreign-policy education. The Alaska summit with Putin mostly reinforced Trump’s alignment with Ukraine and Europe, rather than undercutting it, as many observers originally feared. For advocates of sound and rational policy, going through the necessary paces to have Trump’s illusions stripped away may represent a step forward.

Trump is also susceptible to others’ powers of persuasion. A compelling encounter with the right spokesperson or, occasionally, an individual story can change his mind. Viewing himself as the central protagonist in virtually every drama, Trump is far more interested in interacting with the other players on stage than hearing from aides in the wings, no matter their wisdom.

Trump has expended time and personal effort to secure the release of individual U.S. citizens held hostage by Hamas, Russia, and other foreign forces. These cases, sometimes involving family members’ direct appeals to Trump, seem to move him more than accounts of widescale hardship. When Trump threatened to impose 25 percent tariffs on Mexico early in his current term, a one-to-one conversation with President Claudia Sheinbaum dissuaded him. The abrupt descent of a half-dozen European leaders on Washington in mid-August reflected this understanding: To influence Trump after the Putin meeting, European leaders needed to show up in person.

Although reliance on personal diplomacy is inefficient in that it sidelines seasoned bureaucrats and funnels everything up to the top, it can be the only way forward with Trump. In addition to personal appeals, memorable experiences also make lasting and consequential impressions on him, especially when compared with, for instance, colorless meetings in Brussels. The pageantry of Trump’s May 2017 trip to the Middle East, which included his first visit to Riyadh and a stop at Jerusalem’s Wailing Wall, powerfully influenced him. These moments deepened his interest in relations with Saudi Arabia and firmed up his commitment to Israel. Interlocutors hoping to make an impact on Trump should consider ways to show, rather than tell, what it is they hope he will come to appreciate and understand.

This is not to say that personal diplomacy always works with Trump. South African President Cyril Ramaphosa’s visit to the White House in May was hijacked by a prepared video aimed to substantiate the Trump administration’s insistence that white farmers in the country are under sustained attack; White House political advisors had clearly plotted to seize the moment to underscore these debunked claims about Afrikaners. Where possible, foreign leaders may achieve more if they can stage impromptu encounters with Trump that are less stage-managed by political handlers with an agenda. A hastily planned face-to-face meeting with Zelensky at the margins of Pope Francis’s funeral, for instance, helped repair the U.S.-Ukraine relationship.

One side effect of Trump’s distinctive style is that as his lofty aspirations crash against reality, others come along for the ride. On Ukraine, the Biden administration struggled to shore up congressional and public support for the war effort. But Trump’s bold efforts to push for a resolution, though seemingly futile, have been followed by a surge in pro-Ukraine sentiment among his base. A July poll by the Chicago Council on Global Affairs found that 51 percent of Republicans support sending U.S. military aid to Ukraine, up from 30 percent in March. Over the same period, support for sanctions on Russia also spiked. This suggests that witnessing Trump do all he could to push Putin helped solidify Americans’ recognition of the Russian leader as the aggressor and primary obstacle to peace. (Or that Trump’s base supports him no matter his position, but the net result is the same either way.)

Trump’s idiosyncratic style of international relations presents opportunities alongside pitfalls. Zelensky, Sheinbaum, and European leaders, among others, are learning how to manage a mercurial president who prizes his own ego, instincts, and prerogatives over all else—namely, by honing tactics that rely as much or more on individual psychology as they do policy expertise.