Trump, Master Negotiator? Maybe Against Members Of The NYC Council— Not Against Putin Or Netanyahu

The U.S. Is Headed For Atlantic City-Grade Disasters Under Trump

Want to know how Trump negotiates? Watch the 4-part 2017 Netflix mini-series, Trump: An American Dream. You’ll walk away with the distinct impression that his real estate negotiating style, honed during his decades as a New York developer, is characterized by high-stakes brinkmanship, leveraging publicity, ignorant bluster and a focus on “winning” through bold, often unpredictable moves (also detailed in Tony Schwartz’s 1987 book The Art of the Deal). Señor Trumpanzee constantly used tactics like making audacious initial offers, walking away to create pressure— as in his 1980s acquisition of the Commodore Hotel, where he secured outrageous tax breaks by threatening to abandon the project— and cultivating a larger-than-life persona to intimidate or charm counterparts, often prioritizing short-term gains over long-term relationships. 

No doubt both Putin and Netanyahu— and every other world leader— have watched the series. This approach informs Trump’s failed foreign affairs style, where he similarly employs aggressive posturing, unpredictability, and a transactional mindset— seen in his North Korea summits (2018-2019), where he alternated between threats of “fire and fury” and personal flattery with Kim Jong-un, or his trade war with China, imposing tariffs to force concessions while projecting strength to his domestic base. Neither the substance nor style of his strategies have anything to do with trust, let alone consistency, reflecting his real estate preference for deal-specific victories over sustained partnerships.

Over the weekend, Josh Dawsey and Alexander Ward delved into why Trump’s foreign policy moves are so pathetic and why he’s the ultimate loser. Remember when he promised to end the wars in Ukraine and Gaza on his first day in office. Now he’s frustrated and it keeps him up at night. He told a bunch of cronies at Mar-a-Lago that Putin “was particularly tough to negotiate with, and wanted ‘the whole thing,’ Trump said…The war in Gaza was also notably challenging, Trump told the crowd. Finding any solution was hard because ‘they’d been fighting for a thousand years,’ he said.”

They wrote that “as he passes the 100-day mark of his second term with neither conflict closer to a resolution, negotiations to end Iran’s nuclear program stalled, and a trade war straining relationships with allies, Trump is finding solving the world’s problems more difficult than he had thought. ‘Bluster and theatrics have their role in diplomatic high wire acts, but so do details and hard work,’ said Dan Baer, a former ambassador in the Obama administration who is now at the Carnegie Endowment for International Peace in Washington.”

In recent weeks, Trump has privately griped to advisers that Putin doesn’t want to end the war, and that both sides refuse to compromise. Trump has also asked advisers if they believe Putin has changed since Trump’s last time in office, and expressed surprise at some of Putin’s military moves, including bombing areas with children, according to people familiar with the remarks. 

Earlier this year, Trump said he believed Kyiv would be harder to convince than Russia unless the deal terms were Ukraine’s terms, resulting in a combative Oval Office encounter with Ukrainian President Volodymyr Zelensky live on television. 

More recently, senior Trump administration officials have acknowledged that Russia remains the biggest holdout, refusing to agree to an unconditional 30-day cease-fire that Kyiv has already supported and instead seeking more concessions from Ukraine.

“I wouldn’t say that the Russians are uninterested” in ending the conflict, Vice President JD Vance told a Munich Security Forum event in Washington on Wednesday. “We think they’re asking for too much.”

Trump’s early plans for the conflict were also upended within weeks. Russia complained about Trump’s first Ukraine envoy, Keith Kellogg, over the retired general’s daughter’s support for Kyiv. 

Trump then told Kellogg only to talk with the Ukrainians, and tapped Steve Witkoff, his longtime friend serving as the Middle East envoy, to step in. Kellogg and his team have argued that the diplomat has been effective in getting Kyiv to buy into Trump’s peace process. 

Witkoff has repeatedly pressed both sides to accept some terms they don’t like. Now, Witkoff has told others he just wants to get the two sides to the table, which he hasn’t yet been able to do.

Other U.S. officials have also suggested Trump may consider his job done if he gets the Russians and Ukrainians to engage in serious direct negotiations. What happens after that would be up to them, allowing the U.S. to focus on other priorities, the officials said.

On Gaza, too, the Trump administration is pushing for a negotiated end to the war between Israel and Hamas.

Witkoff helped the departing Biden administration execute its cease-fire plan in January, just moments before Trump took office. But that agreement crumbled in March, and now the war has resumed. Israel has stopped all aid from reaching vulnerable Palestinians in Gaza, sparking a deepening humanitarian crisis.

Israel’s cabinet this week approved a measure to capture all of Gaza should Hamas keep on fighting and hold the remaining hostages. The Israeli government said Hamas has until the end of Trump’s Middle East visit next week to release the hostages.

Some administration officials have been frustrated by Israel’s renewed attacks. But Trump has continued to talk about rebuilding the area, and effectively given Israel the green light to continue its military operations until Hamas changes course.

Meanwhile, Witkoff has widened his net of advisers to prepare for a postwar Gaza, including meeting with former British Prime Minister Tony Blair and lawyer Alan Dershowitz, according to people familiar with the matter.

Both Putin and Netanyahu are smarter and better prepared for high stakes negotiations that Trump. Putin, with his KGB background and over two decades leading Russia, approaches negotiations with a strategic, long-game mindset. His preparation is meticulous— former U.S. officials like Fiona Hill have noted that Putin often comes armed with historical details and intelligence, using this knowledge to exploit weaknesses or create leverage. He’s playing chess while Trump is struggling with go-fish or solitaire. Recall that during the 2017 Hamburg G20 summit, Putin reportedly dominated discussions with Trump by steering conversations to areas where Trump lacked depth, like cybersecurity, while also projecting a calm, unflappable demeanor. Putin’s style relies on patience, psychological manipulation and exploiting divisions, as seen in his handling of the 2016 U.S. election interference fallout, where he denied involvement while sowing discord. Trump, by contrast, often relies on instinct, bluster and a more transactional approach, as seen in his Helsinki summit with Putin in 2018, where he accepted Putin’s denials over U.S. intelligence reports.

Netanyahu, a seasoned politician with a deep understanding of U.S. politics, is known for his preparation and rhetorical skill in negotiations. Having served as Israel’s prime minister for over 15 years across two stints, he’s a master at framing discussions to align with his goals, often using historical and security arguments to appeal to American leaders. His preparation includes leveraging personal relationships and lobbying networks— Netanyahu’s fluency in English and frequent direct appeals to Congress (like his 2015 speech against the Iran nuclear deal) show his ability to navigate U.S. political dynamics. In negotiations with Trump, Netanyahu capitalized on Trump’s pro-Israel stance, securing wins like the 2017 recognition of Jerusalem as Israel’s capital and the 2020 Abraham Accords. Trump’s real estate-honed style— favoring bold gestures and personal rapport— meshed well with Netanyahu’s goals, but Trump’s lack of deep policy knowledge— his limited grasp of the Israeli-Palestinian conflict’s nuances— meant Netanyahu often steered outcomes, as seen when the intellectually lazy Trump endorsed Israel’s Golan Heights claim in 2019 with little apparent pushback. Netanyahu’s preparation and strategic clarity likely made him more adept at shaping negotiations, though Trump’s willingness to break norms gave Netanyahu unprecedented wins.

Both Putin’s and Netanyahu’s structured approaches suggest they’re better at anticipating scenarios and exploiting Trump’s weaknesses, like his impatience or limited policy depth. Trump’s intelligence is more intuitive— he excels at creating leverage through unpredictability but this can backfire when used against disciplined leaders who don’t react to bluster. Both Putin and Netanyahu enter negotiations with Trump better prepared in terms of policy details, historical context and long-term strategy, giving them an edge in setting the agenda. Trump’s preparation focuses on broad strokes and personal dynamics, leaves him vulnerable to being outmaneuvered on specifics, as seen in Helsinki with Putin.

Trump’s right up there with James Buchanan, William McKinley, Woodrow Wilson, LBJ and George W. Bush when it comes to the presidents who have failed— spectacularly— in foreign policy. So far, his foreign policy failures— failed North Korea denuclearization, Iran nuclear escalation, strained alliances and botched peace deals in Gaza and Ukraine— have weakened U.S. strategic positioning and emboldened adversaries like Russia and China.