Trump and his ham-and-Swiss-cheese-sandwich buddy negotiate the fate of the Middle East

If the Russia-Ukraine War peace negotiations (such as there are) look like a challenging tangle even for a master strategist, just think how much more convoluted working out a real, comprehensive settlement of the Israel-Palestine situation would be for our Peace President Trump.

Haaretz’ Yossi Verter sounds gobsmacked by the current situation: 

The first 50 days since Donald Trump's return to the White House have become a crazy geopolitical rollercoaster ride. A new global disorder. While the order of the day is to interpret what Trump did the day before, he springs new surprises the following day, turning the tables completely. (1)

But Trump’s antics make “great television,” as Trump put it in his infamous Oval Office meeting with  Ukrainian President Zelenskyy, amirite?

Writing before the massive new Israeli assault on Gaza, Verter was having a bit of a challenge of what passes for a plot in this reality-TV show:

The problem is that here in Israel (and not only here), we stand dumbfounded at a crossroads branching out in directions that the president has been redefining on a daily basis.

Is it getting the hostages back before all else or "opening the gates of hell" on Hamas? Is it a plan to transfer Gazans out of the Strip and an AI video of Trump and Bibi on Gaza's Riviera, or an Israeli military government, which the Israeli security establishment has fought against? The new army chief of staff, Eyal Zamir, is now hinting that he might actually go along with such a plan.

Verter defines what is often called Trump’s “transactional” type of negotiating this way: “If we are to compare him to the world of commerce, one could say that Trump is turning the ‘American support’ brand into a commodity – merchandise. You want it? Pay for it.“

In other words, he has no evident strategic conception in his diplomacy. He just wants to be able to claim that he made some kind of deal he can brag about. Whether it makes sense doesn’t really matter, as long as it’s marketable in the short run. Verter seems to be worried that his might work to Israel’s disadvantage particularly in relations with Saudi Arabia. But he doesn’t really elaborate on that point, so it’s not entirely clear what he means there. Trump has certainly been deferential to Benjamin Netanyahu in both his President terms, so far. And the remainder of Verter’s column is taken up describing Netanyahu’s ongoing effort to get out of corruption charges and establish and more and more authoritarian government in Israel itself.

Trump’s negotiator with Israel is Steve Witkoff, who seems to be someone in whom the Orange Anomaly places a large amount of confidence, at least for the moment. He’s had Witkoff involved in the Russia negotiations over Ukraine. And he’s also working on a new diplomatic arrangement between Azerbaijan and Armenia. (2)

Steve’s a busy guy. Trump claimed not to believe reports that Putin made Witkoff wait for six hours to meet with him last week. Trump and he go back with each other:

Witkoff, who runs a real estate development and investment firm, is a longtime friend and golf partner of Trump. He played a less visible role during Trump’s first term, serving on the board of trustees for the John F. Kennedy Center for the Performing Arts.

Witkoff first met Trump in the 1980s, when he worked for a real estate law firm that handled a deal for Trump, himself a real estate developer, according to testimony Witkoff gave in the president’s civil fraud trial in 2023.

Witkoff testified that a few years later, he ran into Trump at a deli. Trump didn’t have money with him and asked Witkoff to order him a ham and Swiss cheese sandwich. Years later when they met again, Trump remembered the sandwich and the two became friends, Witkoff said.

He’s been more than a friend. Witkoff has donated millions to Trump’s political causes over the years. He also partnered with Trump on the president’s family cryptocurrency venture, World Liberty Financial. (3) [my emphasis]

It almost makes you nostalgic for the days when Henry Kissinger was the Republicans’ star traveling diplomat. There are volumes filled recounting Kissinger’s misdeeds. But he actually did have a strategic vision of what he was doing.

But it’s not hard to imagine why Trump likes him, in addition to the campaign cash he get from him. Oh, he’s also threatening war on Hamas, though it’s not entirely clear if he means direct war by the American Peace President or by Netanyahu and The World’s Most Moral Army (though it seems to be the latter).

U.S. special envoy Steve Witkoff said on Sunday that he is encouraging Hamas to get much more sensible than they have been. Witkoff spoke to CNN and said that his proposal for a bridging agreement that would see the immediate release of five live hostages, including American Israeli citizen Edan Alexander, and extending the first phase of the ceasefire, is compelling. The Hamas response, he said, is unacceptable.

"I believe they have an opportunity, but it is slipping away quickly. What happened with the Houthis yesterday, what happened with our strike, ought to inform as to where we stand with the regard to terrorism and our tolerance level for terrorist actions - and I would encourage Hamas to get much more sensible," Witkoff said. [my emphasis] (4)

The Saudi concern to which Yossi Verter refers has to do with diplomatic maneuvering going on involving the US, Russia, Saudi Arabia, and the United Arab Emirates (UAE). As Zvi Bar'el explains it:

Those steps include the relationships that Saudi Arabia has built in recent years with both Moscow and Washington by ignoring American sanctions against Russia while simultaneously offering to invest $600 billion in the U.S., as well as the control it wields over OPEC – and thus over the price of oil on global markets. The expectation that it will fund the reconstruction of Lebanon, Syria and maybe Gaza, as well as the longstanding ties between the Trump family and that of Crown Prince Mohammed bin Salman, have also been essential in transforming the kingdom's role on the global stage.

The UAE is Russia's most important trading partner in the Middle East, and like Saudi Arabia, it has ignored Western sanctions on Moscow. But its ruler, Mohamed bin Zayed, also has warm relations with Zelenskyy. The two signed a major economic cooperation agreement that could even help Kyiv cover the funding shortfall created by Trump's decision to end U.S. aid to Ukraine.

Israel is not part of this web of relationships and, even worse, risks being seen as an obstacle preventing Trump's apparent vision for reshaping global alliances. In this new geopolitical map, Russia would ally with the U.S. against China, Iran would sign a renewed nuclear deal, and the Gulf states would provide a safety net – both countering China's influence and offering huge investments in exchange for neutralizing Iran's nuclear threat. [my emphasis] (5)

Can the Orange Anomaly and his ham-and Swiss-cheese-sandwich buddy Witkoff pull off a complicated Kissingerian diplomatic scenario like this? Or will it go the way of Trump’s first-term effort to get North Korea not to develop nuclear weapons?

Notes:

(1) Verter, Yossi (2025): Trump Has Commodified U.S. Support, and Israel Is Bound to Pay. Haaretz 03/14/2025. <https://www.haaretz.com/israel-news/2025-03-14/ty-article/.premium/trump-has-commodified-u-s-support-and-israel-is-bound-to-pay/00000195-9131-d4eb-a9fd-d3711d190000?lts=1742247476616> (Accessed: 2025-17-03).

(2) Trump envoy Witkoff in Azerbaijan for talks after Netanyahu, rabbis' involvement. Jerusalem Post 03/14/2025.<https://www.jpost.com/international/article-846086> (Accessed: 2025-17-03).

(3) Price, Michelle & Madhani, Aamer (2025): Steve Witkoff has gone from spotting Trump cash at a deli to helping him navigate Ukraine and Gaza. AP News 03/13/2025. <https://apnews.com/article/steve-witkoff-special-envoy-russia-ukraine-mideast-d26c80c87a57fd3a811e4b0aa0eda58e> (Accessed: 2025-17-03).

(4) Witkoff threatens Hamas after 'unacceptable response' in negotiations, says 'consider what US did to the Houthis'. Ynet News 03/16/2025. <https://www.ynetnews.com/article/r1o100vnh1g> (Accessed: 2025-17-03). The ham-and-cheese sandwich story is weird and dorky enough to possibly be true.

(5) Bar’el, Zvi (2025): Israel Risks Being Sidelined in Trump's Tangle of Interests as He Overhauls Global Politics. Haaretz 03/10/2025. <https://www.haaretz.com/israel-news/2025-03-10/ty-article/.premium/as-trump-seeks-to-transform-global-geopolitics-israel-must-think-much-bigger-than-gaza/00000195-7cba-d0f8-a1f7-7cfbe4960000?gift=d623d67fc61e473caf0525c5931d3a9a> (Accessed: 2025-17-03). Yes, the idea of Trump overhauling global politics does sound scary.