The White House, Real Estate and Quicksand

The author of “The Art of the Deal” deftly negotiated two elections with the American people and improbably landed himself in the White House. After surviving two impeachments and assassination attempts, Donald Trump returned to the Oval Office like the Terminator, promising “Hasta la vista, baby” to the old way of doing things.

Like him or hate him, he has disruptively shattered the mold on American politics. His brashness was no surprise, however. Back in the 1980s, he was a young real estate developer with a fondness for gilded towers bearing his name. The buildings were always less important than the brand.

New York real estate movers and shakers are generally not known for making much noise. Not Trump, who luxuriated in luxuries and headlines. He purchased the New Jersey Generals in the fledgling United States Football League and sued the NFL for exploiting its monopoly over the game. He received $1 in damages.

His next venture was as a casino magnate in Atlantic City. He then licensed his name for steaks, men’s ties, an airline, even a university. All failed.

But his Q-Rating never dimmed, especially after he became a reality TV star, which introduced him to Red State America in ways his real estate portfolio could not. Ronald Reagan was once a pitchman for dress shirts, cigarettes and TV sets; Trump always hocked himself.

But his hubris may have met his match in foreign affairs, where his ambitions are many and his experience sparse. Ending wars in Gaza and Ukraine. Jumpstarting relations between Israel and Syria, and Israel and Turkey. Disarming Hezbollah in Lebanon. Deepening ties between Sunni Arab states and Turkey as a bulwark against Iran, China and Russia.

Previous Democratic administrations were perversely naïve in their flirtations with Iran and its nuclear aspirations. Trump may be exhibiting some gullibility of his own. He seems willing to trust the one country that speaks of wiping other nations from the map.

Previous Democratic administrations were perversely naïve in their flirtations with Iran and its nuclear aspirations. Trump may be exhibiting some gullibility of his own. He seems willing to trust the one country that speaks of wiping other nations from the map.

All tall orders for a guy not known for diplomacy and who isn’t impressed with those schooled in foreign affairs.

He’s a real estate developer, after all. Never before has so much responsibility in international relations be given to someone whose view of the world has been shaped exclusively by square feet, mortgage deeds, and cash flow.

Never before has so much responsibility in international relations be given to someone whose view of the world has been shaped exclusively by square feet, mortgage deeds, and cash flow.

During Trump’s first term, Jared Kushner, the scion of a real estate family, was charged with negotiating the Abraham Accords, and devising a Peace to Prosperity plan to resolve the conflict between Israel and the Palestinians. The first endeavor was an overwhelming success. The second drew absolutely no interest from the people it was intended to benefit.

Trump couldn’t fathom a people with so little interest in peace and not incentivized by prosperity. Five years later Trump looks upon the Gaza Strip as he would the Las Vegas Strip—except that Gaza has waterfront property, making it even more valuable.

It’s a shame land speculation and territorial disputes have so little in common. A working knowledge of real estate is useless in appeasing ancient enmities—especially among non-Western nations. Deal-making in international affairs is an art, not a science. Beware getting swindled at the souk. It can happen to the most seasoned value investor.

Take Steve Witkoff, another billionaire whose fortune was built by owning buildings. This is the man Trump has charged with closing deals with Hamas, Iran and Russia.

He’s not having an easy go of it. In Gaza he’s dealing with a terrorist organization that acts like it is holding all the cards. Despite a poor negotiating position, they insist on ignoring the deal on the table and demanding instead a seven-year ceasefire, a complete withdrawal of the IDF, and the retention of power over the enclave.

Oh, and they want a trip to Disney World, too.

Neither Trump nor Witkoff have any experience negotiating with people who believe that compromise is a sign of abject weakness. In a real estate closing, certain gestures might soften the other side. Witkoff let it be known that Hamas is “not as ideologically extreme as they are portrayed.” Big mistake. He lavished praise on Qatar in serving as an intermediary, too.

Beware Qataris bearing gifts. Trump walked off with a new luxury jet that will serve as a revamped Air Force One. The Qataris now believe they have wiped clean the blood on its hands for having shown such hospitality to Hamas.

Witkoff reassured the world that Syria’s new leader, Ahmed al-Sharaa, is a changed man from the days when he was associated with al Qaeda.

How would a Jew from the Bronx who has never lived in the Middle East or confronted a terrorist possibly know that?

Witkoff is especially out of his depth in his dealings with Iran. The Ayatollahs have been playing nuclear chess while Trump and Witkoff toy with their Monopoly boardgames. Iran enriches uranium on the sly while dodging regulators from the International Atomic Energy Agency. They have been doing it for so long, it’s difficult to imagine that they don’t already pose a nuclear threat to the West.

Meanwhile, it seeks sanctions relief, access to global financial centers and international trade. In return the United States will receive a friends and family discount on Persian rugs.

Vladimir Putin is already providing Iran with funding to build a new nuclear facility and expand an existing one. China is blowing nuclear waste in Witkoff’s face, too. Together with Russia they are working to convince the United Kingdom, France and Germany not to reimpose sanctions on the Shiite state.

Witkoff isn’t merely vulnerable to obsequious Arabs. He seems deluded by Putin’s duplicity, too, even though the former KGB agent once specialized in deceiving the West. Witkoff has lent support for Russia’s war in Ukraine and seems convinced that Putin has no interest in invading Europe or any other parts of Ukraine. He has also expressed a fondness for Putin, calling him a “great guy,” “super smart” and “honest.”

Perhaps all this should be expected. Witkoff is not the first to misconstrue Islamic and Russian intentions. To succeed as a negotiator in world conflicts, it takes a very different kind of savvy than what is required in brass-knuckle real estate transactions. One needs to know how to read the diplomatic room. Hamas, the Ayatollahs and Putin are a different breed of adversaries. There are no balance sheets or capital gains by which to measure success.

Perhaps Witkoff’s faith in his own, and his boss’, statesmanship will yield a different kind of dividend. Either he’ll be proven right and forever regarded as a savant in the diplomatic corps, or remembered as an outmatched pretender who had none of the qualities of a Henry Kissinger, George Schultz, or Abba Eban.

Thane Rosenbaum is a novelist, essayist, law professor and Distinguished University Professor at Touro University, where he directs the Forum on Life, Culture & Society. He is the legal analyst for CBS News Radio. His latest book is titled, “Beyond Proportionality: Israel’s Just War in Gaza.”