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When Ukrainian and Russian officials met for a second round of cease-fire discussions in Istanbul on June 2, it was obvious that there would be no serious negotiation. Ukraine, eager to satisfy the Trump administration’s desire for a settlement, was represented by a high-level delegation headed by its defense minister. Russia, however, only sent low-level diplomats. With the exception of opening the door to a new prisoner exchange, the meeting brought no breakthroughs. Instead, the Kremlin presented the terms—unchanged for three years—for Ukraine’s submission, including recognition of Russian dominion over five occupied Ukrainian regions, the cession of additional territory by Ukraine, Ukrainian neutrality, and the de facto de-militarization of its armed forces.

While European representatives came to Istanbul in a demonstration of support for the peace process, the United States was noted for its absence, evidence that it has been sidelined from playing a principal role in the negotiations. This is a far cry from the heightened expectations for the peace process and a clear step away from the hopes that attended the initial meetings in May, when U.S. President Donald Trump indicated that he was ready to come to Istanbul if Russian President Vladimir Putin also showed up.

Trump has long touted his special relationship with Putin and made peace in Ukraine a major foreign-policy aim, but Washington’s absence was stark evidence of the failure of the administration’s diplomacy and overall approach to the Russia-Ukraine war. This failure is the product of incompetent negotiations, a lack of understanding of Russia’s true ambitions, and a misreading of Putin’s signals. The failure ultimately rests on Trump’s shoulders, but it has been seriously exacerbated by the influence of his main emissary to the Kremlin, the amateur diplomat Steve Witkoff.

Witkoff’s ascent into high-stakes diplomacy was one of the greatest surprises of the second Trump administration. Until last November, Witkoff stood far outside the foreign-policy process. His initial public role was co-chair of Trump’s inaugural committee. But on Nov. 12, 2024, Trump assigned Witkoff to his first stab at international relations, as Trump’s special personal envoy to the Middle East. Initially, and with the outgoing Biden administration’s consent, Witkoff engaged with Israel and Hamas. After Trump’s inauguration, Witkoff’s role became an official U.S. government one.

Witkoff, who has known Trump for four decades, is a leading Trump loyalist, friend, and golf partner. Significantly, Witkoff offered companionship and moral support to Trump during his most difficult days in the aftermath of the Jan. 6, 2021, insurgency and when Trump faced a felony conviction in New York City in early 2024.

Born in the Bronx, Witkoff studied at Hofstra University on New York’s Long Island, and pursued a law career that morphed into real estate development and investments that made him a billionaire. Often partnering with Soviet expat Len Blavatnik, who made his fortune in post-Communist Russia, Witkoff amassed a vast portfolio of U.S. real estate, highly concentrated in New York City, Miami, and California. Although his company had some international business activities focused on several high-profile investments in London, they represent a minor portion of the portfolio. Witkoff’s lack of foreign business experience made him fundamentally different from the other business leaders Trump has tapped to implement U.S. foreign policy.

Witkoff greets relatives of Israeli hostages in Tel Aviv on May 13. Jack Guez/AFP via Getty Images

Witkoff’s first stab at diplomacy focused on securing a cease-fire and hostage release in the Hamas-Israel war. Working hand in hand with Brett McGurk, a senior foreign policy official in the Biden, first Trump, and Obama administrations, Witkoff successfully brokered a short-term agreement just days before Trump’s inauguration. Though the deal, which lasted 60 days, expired and the conflict continued, the tag team of seasoned diplomat and trusted intimate of the incoming president worked well, bolstering Witkoff’s reputation.

Soon after his Middle East success, Witkoff’s portfolio was dramatically expanded with the added roles of directly negotiating with Russia and Iran. With the exception of history’s diplomatic legends—the Austrian Empire’s Klemens von Metternich, for example, or the United States’ Henry Kissinger—the responsibility for multiple, high-stakes international negotiations is rarely handed to a single official.

Still, the appointment of someone with a close personal connection and direct access to the president has proved successful in the past. It worked exceptionally well during the negotiations over the Abraham Accords, in which Trump’s son-in-law, Jared Kushner, played a central role while relying on a large team of experienced advisors with long-standing knowledge of the Middle East.

Yet when it came to Russia, Witkoff shifted gears. Instead of working in close cooperation with U.S. government experts, he ran what was essentially a one-man show. Controversially, he avoided significant engagement with the U.S. Embassy in Moscow or the State Department back in Washington. Like Trump has done in the past, he even eschewed the use of a U.S. interpreter or notetaker in his meetings with Putin. Reliance on a Kremlin interpreter meant that he did not have the benefit of a nuanced read of Putin’s original language, an unprecedented decision widely criticized by foreign-policy professionals.

Moreover, in the first months of negotiations, Witkoff had no contact with the Ukrainian side. Given his near-total unfamiliarity with Russia, Ukraine, and their long and bitter history, Witkoff’s decision to go it alone meant that he arrived at the Kremlin with little or no knowledge of Ukraine’s legitimate red lines and had no context in which to assess Putin’s claims and signals.

In a photo distributed by the Russian state-owned news agency Sputnik, Witkoff (left) gestures toward Russian President Vladimir Putin during talks in Moscow on April 25. Kristina Kormilitsyna/Sputnilk/AFP via Getty Images

Although Witkoff did seek advice from such diverse sources as former British Prime Minister Tony Blair and former U.S. President Bill Clinton, Witkoff’s lack of regional knowledge and unfamiliarity with the conduct of diplomacy led to a string of errors. Unlike seasoned negotiators, who speak opaquely and conduct their work quietly, Witkoff regularly commented on the state of negotiations, often making definitive and bold assertions of “significant progress” that usually failed to materialize. Just as significantly, his diplomacy was undermined by his penchant to side with the Russian narrative and to publicly make unilateral, preemptive concessions to Russia without any evidence that the Russians would reciprocate with any concessions of their own. These unilateral concessions—announced by Witkoff and other administration officials—included U.S. rejection of Ukraine’s membership in NATO, a deep reduction in U.S. aid to Ukraine, and declarations that Ukraine should recognize Russia’s territorial conquests.

To be sure, Trump has also adopted Russia’s line on many aspects of the war. He has hyped the state of negotiations with Russia, suggesting at various times that a cease-fire was just around the corner and would soon lead to a more permanent peace. But he has balanced such comments with occasional complaints about Russian belligerence and intransigence. Not so Witkoff, who appears to believe peace will come if he ingratiates himself with Putin, talks up vast new joint investment partnerships, and praises Russia for its supposed readiness to make major strides toward peace.

Witkoff’s central role in negotiations with Russia had another harmful effect. His close personal relationship with Trump meant that Witkoff’s assessment of Putin’s intentions superseded those of more hard-headed experts. Witkoff thus reinforced Trump’s dubious belief that Putin can be wooed from his alliance with China by vague promises of U.S. trade and investment.

Witkoff’s most complete explication of his views on Russia, Ukraine, and the war came during a March 21 broadcast with the notorious anti-Ukraine pundit Tucker Carlson, known for praising Putin’s Russia as a model of prosperity and deriding Ukraine as a “dictatorship.” The interview revealed Witkoff’s shocking lack of knowledge about Ukraine, Putin, and the nature of the Russian regime.

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Witkoff optimistically suggested that “we’re not far away from … a 30-day cease-fire” even as Russia continued a major military onslaught and pounded civilian targets in Ukrainian cities in the days before he spoke.

What’s more, Witkoff defended Putin as not a “bad guy” and a “gracious” and “great” leader. The envoy was indifferent to or unaware of Putin’s responsibility for more than 10,000 Ukrainian civilian deaths, the displacement of as many as 10 million people, the impunity of Russian soldiers and mercenaries who perpetrated summary executions of Ukrainian civilians and prisoners of war, and the war crime of abducting Ukrainian children, as documented in the arrest warrant for Putin issued by the International Criminal Court.

Even more incredibly, Witkoff has uncritically repeated Russian tropes about the war. In February, he told CNN that “the war didn’t need to happen. It was provoked. It doesn’t necessarily mean it was provoked by the Russians.” He augmented Russia’s narrative by telling Carlson that the regions Russia had occupied (whose names he could not recall) were “Russian-speaking,” implying that this was a marker of loyalty to Moscow and a legitimate basis for Russian annexation.

In reality, more Ukrainians have fled the occupied Donbas into Ukraine since 2014 than those who stayed to live under Russian rule; both Russophone Ukrainians and inhabitants of eastern Ukraine have been heavily represented in Ukraine’s combat forces; and polls since Russia’s 2014 invasion have consistently shown Ukrainians from Russian-speaking eastern and southern Ukraine decisively reject the idea of annexation or unification with Russia.

Witkoff further seemed to accept the validity of Russia’s sham referenda on annexation, which took place under martial law and press censorship; violated the Geneva Conventions; excluded neutral international election monitors; and took place in a climate of fear of arrest, torture, and execution. Witkoff also claimed that all Russia wants is the territories it currently holds and has no desire to annex any additional territories or destroy the rest of the country. There is no evidence that Putin has ever made such a statement.

In short, Washington’s envoy was doing his best to lend credibility to Russia’s territorial claims using arguments that displayed no awareness of Russian ambition and Ukrainian reality.

U.S. President Donald Trump invites Witkoff to respond to a question from the media in the Oval Office of the White House on May 28.Andrew Harnik/Getty Images

Following Trump’s inauguration, the United States rapidly abandoned its role as a supporter of Ukraine and assumed the role of neutral arbiter. Witkoff’s diplomacy, interpretations of the war, and echoing of Russian claims have gone beyond neutrality to align the U.S. position with the Kremlin’s, at least in part. This has raised alarms among NATO allies and led Europe to bolster Ukraine, independent of U.S.-Russian negotiations.

Each of Witkoff’s assignments—Russia-Ukraine, Israel-Hamas, and Iran—would pose vast challenges for any diplomat. But his extravagant promises of rapid breakthroughs have only underscored the absence of progress. With about half a year of diplomacy behind him, Witkoff’s record has been meager. His negotiations have gone nowhere on Russia-Ukraine, devolved into an impasse on Israel-Hamas, and been overtaken by events in Iran.

Although Witkoff’s diplomacy has spectacularly failed, he is likely to continue to play a major role in U.S. diplomacy. After all, Witkoff’s engagement burnishes Trump’s desired image as a “peacemaker” and “peace seeker,” roles that allow him to create the impression of U.S. engagement with the world that straddles the chasm between traditional national security Republicans and MAGA isolationists. Just as significantly, Witkoff has reinforced a perniciously inaccurate read of Russia’s actions and intentions and thus diminish the chances for a negotiated peace.

Following the reassignment of National Security Advisor Michael Waltz, there was speculation that Trump may be considering Witkoff for the post. Given Witkoff’s demonstrated record of incautious concessions, counterproductive diplomacy, dismissal of expert counsel, and superficial knowledge of international affairs, such an appointment would be an unmitigated disaster for the United States. In the end, Witkoff’s role as an errant diplomat underscores the fact that the role of civil servants, intelligence experts, and the foreign-service community—what Trump disparagingly calls the “deep state”—cannot be replaced with personal operatives with only a shallow knowledge of international affairs.