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Adam Boehler: The bewildered envoy at the heart of Trump’s hostage policy

Simon Kupfer
6 min readMar 14, 2025
Adam Boehler talking at an event with Mexico’s Foreign Minister, Marcelo Ebrard in Mexico City on November 8, 2019. Source: The Jerusalem Post/REUTERS/Luis Cortes

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Adam Boehler’s involvement in Middle East diplomacy was unorthodox from the start of his appointment: a former healthcare executive and longtime Trump associate, thrust into the complex reality that is the political predicament of one of the most volatile regions on the planet.

As Trump’s appointed hostage envoy, his direct engagement with Hamas has been marked by masses of confusion, a good few missteps, and an increasingly worrying divergence from Israel’s established negotiating stance. His recent claim that the United States is ‘not an agent of Israel’ highlights a troubling shift in American foreign policy: one that not only presents the US as separating itself from Israel, but also one that risks undermining Israel’s position and risks emboldening Hamas at a critical moment in the war.

Boehler’s primary mandate was to secure the release of the hostages held by Hamas post-October 7, when Hamas terrorists infiltrated Israel and killed 1200, abducting 251. His lack of understanding of political tradition was severe to so great an extent that David Horovitz declared him ‘complacent, confused and dangerously naive’ in a Times of Israel article detailing his many flaws — Horovitz described, in detail, over a dozen — earlier this week. He pursued direct talks with Hamas, bypassing traditional Qatari and Israeli intermediaries, casting aside the US’s long-standing policy of declining to engage with Hamas directly — it being a designated terrorist organisation and all — while insisting that such an approach was necessary to expedite the release of American and Israeli hostages.

His ‘approach,’ if one may call it that, appears to be based on the assumption that a personal rapport and economic incentives could persuade Hamas to soften its position. The reaction from Israeli officials, of course, was one of alarm. A sceptic might go so far as to suggest that Boehler’s ‘outreach’ undermines any sense of leverage Israel possesses, legitimises Hamas’ position — or both. Boehler was dismissive of Israeli Minister of Strategic Affairs Ron Dermer’s anger over his direct talks with Hamas. On Channel 13, Boehler said, ‘I don’t really care about that that much — no offense to Dermer. If it was a big deal every time Dermer got a little bit upset… Ron might have a lot of big deals every day.’ He softened the blow by adding, ‘I love Ron. We’ll work together again. It was great. I take no offence because he was doing what he was supposed to do.’ Dermer’s anger is not merely an obligation to his people, ‘doing what he was supposed to do’ as Boehler views it, but an entirely justified outrage at the US electing to prioritise its own interests over the collective welfare of Israeli and American hostages.

Boehler has made quite the variety of missteps in his short time as the United States Special Presidential Envoy for Hostage Affairs: he has repeatedly misused terms fundamental to the unstable situation, referring to Palestinian security prisoners, some of whom are tried and convicted terrorists, as ‘hostages’: in an interview with Israeli Channel 13, he stated, “They are exchanging massive amounts of hostages for one person,” seemingly conflating Palestinian prisoners with Israeli hostages, while conversely referring to the same Israeli hostages as ‘prisoners’ in an interview with CNN, where he said, ‘I think there is a deal where they can get all of the prisoners out, not just the Americans.’

There are three possible reasons for Boehler’s words: the first, he does not know the difference; the second, he legitimately views the Palestinian terrorists as ‘hostages’, and the Israeli captives as ‘prisoners’; and the third, he simply is not invested enough in his occupation to care. I, for one, do not know which is worse. To make matters worse, Boehler misnamed the sole American citizen among the remaining hostages, Edan Alexander, instead calling him ‘Adi’, his father’s name, in multiple interviews. For a negotiator whose job revolves almost entirely around securing the release of a small group, such a level of carelessness is deeply troubling.

Edan Alexander. Source: ynet

Boehler’s flawed approach to negotiating with Hamas reflects an alarming degree of misplaced trust and moral relativism. He told CNN that his strategy involves identifying himself with the ‘human elements’ of Hamas leaders, claiming in the discussion that ‘the most productive approach is to realise that every piece of a person is a human.’

To humanise a terrorist organisation is to grant it legitimacy. Hamas was stripped of whatever small slivers of compassion it may have had left when it attacked Israel on October 7, 2023.

He went so far as to describe Hamas as a group of ‘nice guys’ in a somewhat convoluted defence of his approach: ‘Maybe I would see them and say, ‘Look, they don’t have horns growing out of their head. They’re actually guys like us. They’re pretty nice guys.’

This, of course, was met with an immediate backlash, and so Boehler issued a clarification: ‘Hamas is a terrorist organisation that has murdered thousands of innocent people. They are BY DEFINITION BAD people. And as @POTUS has said, not a single Hamas member will be safe if Hamas doesn’t RELEASE ALL HOSTAGES IMMEDIATELY.”’ His style, capitalising entire words, seems awfully similar to that of his President — not the best example of character — see here a list of false or misleading statements by Trump.

Even more concerning, though, is Boehler’s confidence that Hamas will ultimately dissolve itself peacefully: when asked whether Hamas would realistically lay down its weapons and abandon political control of Gaza, Boehler answered, ‘I do believe that.’ Such a view is beyond naive: Hamas is a terrorist organisation that pledges to remove the State of Israel from the map. Ghazi Hamad, a member of Hamas’s political bureau, told Lebanese television barely two weeks after the massacre of the 7 October that ‘Israel is a country that has no place on our land.’ He declares, ‘The Al-Aqsa Deluge is just the first time, and there will be a second, a third, a fourth… Nobody should blame us for the things we do. On October 7, October 10, October one-millionth, everything we do is justified.’

Militants in Gaza. Source: BBC/Getty images

Boehler’s blunders have exacerbated an already increasingly volatile political situation. Netanyahu’s inconsistent handling of the hostage crisis created the political void into which Trump inserted Boehler, after Israeli Prime Minister Netanyahu backed away from a phased hostage-release/ceasefire deal in May that he had previously agreed to, leaving Hamas in control of the pace and terms of negotiations. Such indecision has allowed Hamas to enjoy the benefits of the ceasefire, to regroup and rearm; all without releasing any additional hostages — and likely angered Trump more, given his ‘America first’ policy that prioritises the interests of the US above all else, desiring to be seen as an international dealmaker. This includes its alliances: see the heated argument between Trump and Zelenskyy in the White House a few weeks ago.

Boehler publicly differentiated between American and Israeli interests, declaring in the same sentence as his ‘agent of Israel’ expression, ‘we’re the United States. We’re not an agent of Israel. We have specific interests at play.’ Surely Trump, the so-called ‘leader of the free world,’ should be more occupied with the welfare of his citizen, Eden Alexander, held captive in Gaza for the past eighteen months, than economic and political motivations?

Ultimately, Boehler’s performative statements and actions function not solely as indictments of his personal misjudgement — they are symptoms of the broader dysfunction that now defines Israel-US relations in the wake of 7 October. His handling of the crises he has presided over reflects a dangerous combination of diplomatic naivety, strategic confusion, and deep political miscalculations. If he is the future of Israel-US relations, the future looks bleak.

Thanks for reading today’s article, everyone — maybe even give another one a read while you’re at it.

If you think anything should be included, either in an edit to this article or in a future one, do let me know.

It’s also worth saying that articles like this are based on incredibly controversial topics. If you disagree with me, I invite your arguments in the comments.

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Good day — Simon

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Simon Kupfer
Simon Kupfer

Written by Simon Kupfer

Author and prolific coffee drinker. Contributor to the Times of Israel.

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