A Broken Record: Trump's negotiation strategies have had limited success in the past, but now they are perceived by counterparties as a familiar script with well-known vulnerabilities
In his approach to the Ukrainian issue, Trump is replicating the strategies he used when preparing for the withdrawal of US troops from Afghanistan. However, his direct negotiations with the Taliban, which was conducted behind the back of the US-backed Afghan government, resulted in the latter’s total collapse and a chaotic retreat for American forces. Meanwhile, in his dealings with Putin, with whom he hopes to strike a 'big deal', Trump is mirroring his approach to negotiations with Kim Jong-un in 2018–2019, which ultimately led to no tangible results.
Trump has positioned himself as a master negotiator and dealmaker. His strategies typically involve excessive initial demands, the artificial creation of time pressure, the undermining of his own allies, and attempts to achieve a breakthrough through direct personal engagement, bypassing intermediaries.
By applying hardball business negotiation tactics to international relations, Trump disrupts diplomatic norms and established protocols. While the tangible outcomes of his high-profile initiatives tend to be modest at best and disastrous at worst, he often manages to frame these results as successes.
The aggressive business negotiation model treats deals as one-off transactions in a zero-sum game. When applied to international relations, this approach erodes long-term trust, even when a deal appears successful – since any gains tend to be short-lived and marginal. Trump dismantles old alliances but fails to build new ones.
Finally, a critical flaw is that Trump’s repertoire of tactics remains unchanged and is now well known to his counterparts, who have learned to exploit its weaknesses.
At the same time, his obsession with securing a 'big deal' that would earn him a Nobel Prize is growing with each failure – just like his belief that the main obstacles in his way are his foreign allies, whose opinions he disregards, and his domestic opponents, over whom he seeks to assert dominance.
A broken record
Donald Trump sees himself as a great negotiator and master deal-maker. His 1987 book, The Art of the Deal, is considered almost essential reading for those looking to succeed in the art of negotiation. While Trump’s aggressive business negotiation style is not new in itself, the fact that a staunch proponent of this approach has become US president for a second time and is applying it to international relations effectively transforms it from a mere tool into a new ideology.
In an article for Negotiation Journal, Thomas Kochan, a professor at the MIT School of Management, identifies five main traits of Trump as a negotiator: 1) He views negotiations through a 'distributive lens' (win-lose) and sees his own position as dominant; 2) He seeks personal satisfaction and recognition, making him susceptible to flattery and willing to trade concessions for displays of respect; 3) He treats deals as one-off transactions, which hinders the development of long-term relationships and trust; 4) He tends to launch personal attacks and insults against those who oppose him; 5) He has weak barriers when engaging with partners of dubious reputation and low ethical standards.
Trump’s primary negotiation strategy is the use of pressure and force, tactics he employed as a New York real estate developer, writes Jim Schlexer, CEO of The CEO Project, a consulting firm, in another article on the subject. Another key feature of Trump’s negotiation style is exaggeration, which he refers to in his book as 'truthful hyperbole'. For example, when sourcing construction materials, Trump would threaten suppliers with finding much cheaper alternatives that, in reality, did not exist.
Trump begins negotiations with an outrageous demand, a technique often called anchoring. He puts forward deliberately unrealistic conditions and makes political statements that sound absurd—such as his supposed desire to annex Canada or occupy Greenland. This tactic immediately shifts the negotiating space in his favor, forcing counterparts to start making concessions even before talks begin. Another key tactic is the creation of 'artificial time pressure'. By manufacturing a sense of urgency, Trump forces the other party to act quickly and make concessions under the threat of the deal falling apart, write the authors of The Negotiation Club blog. During 2018 negotiations with South Korea over revising a free trade agreement, he repeatedly threatened to unilaterally withdraw, ultimately pressuring Seoul into making certain concessions, Schleckser notes.
Finally, Trump also extensively uses 'strategic unpredictability' as a tool for pressure and dominance. Another critical aspect of his negotiation style is his obsession with publicity. In defiance of diplomatic norms, he often live-tweeted updates on negotiations, calling it part of his strategy. Typically, this public exposure served to discredit his negotiating counterparts.
Running on distrust
Over the past month, Ukrainian President Volodymyr Zelensky and other Ukrainian negotiators have faced Trump’s full arsenal of tactics. Trump managed to call Ukraine’s president a dictator and a fraud, only to 'forget' his words within two days. He constantly pressures the Ukrainian side under the pretext of pushing for a quick ceasefire—something that is obviously beyond Zelensky’s control. Finally, he loudly emphasises disagreements between the parties, shaping American public opinion against the Ukrainian president (→ Kirill Rogov: A Game Without Trump Cards).
Trump’s negotiation strategy can sometimes bring success, particularly when the counterpart is in a vulnerable position and unwilling to confront him. However, even these victories can be undone. If Trump’s 'win' is acknowledged and his ego is satisfied, the other party—having accepted defeat—may later reclaim concessions and mitigate the damage. For instance, during his previous term, Trump renegotiated the North American Free Trade Agreement (NAFTA), which he repeatedly called the 'worst' deal, replacing it with the United States-Mexico-Canada Agreement (USMCA). Despite the high-profile political rebranding, analysts note that the new deal is not significantly different from the old one, and many of its new provisions were already being discussed in quiet pre-agreement negotiations. A detailed analysis of Trump's new trade agreement with South Korea leads to similar conclusions: in substance, it barely differs from its predecessor. Thus, Trump’s 'deals' often appear revolutionary, global, and even unthinkable at the start (the anchoring phase). They are surrounded by an atmosphere of scandal and confrontation, where Trump must emerge victorious. However, in reality, they result in only minor progress on difficult issues – or turn out to be mere political theatrics with little substance. A prime example of this phenomenon is the proposed resource agreement with Ukraine (→ Re:Russia: Shackles, Chimera or Marshall Plan?).
Martin Latz, founder of a prominent consulting firm, told Politico that while Trump built his career on promoting himself as a successful negotiator, this perception is far from reality. A truly skilled negotiator is distinguished not just by assertiveness but by the ability to confidently articulate a position based on deep knowledge of the issue. In Trump’s case, it is precisely his lack of preparation, incompetence, impulsiveness, reliance on threats and insults, and zero-sum mindset that often lead negotiations to a dead end, Latz argues.
The long-term consequences of this approach are overwhelmingly negative. Trump’s aggressive style undermines relationships with allies and established alliances, prevents compromise in critical negotiations, and leads to unnecessary escalation, notes Schleckser. Applying a business approach to international relations – where each deal is treated as a one-off brawl rather than part of a long-term diplomatic strategy – erodes trust that takes decades to build. As a result, Trump’s deals destroy old alliances without creating new ones.
Phase I agreements
Beyond the much-criticised 'China deal', which even Trump’s own administration viewed as a failure and labelled a 'first-phase' agreement, three of Trump’s major diplomatic efforts are worth examining: the Abraham Accords, negotiations with Kim Jong-un, and the Taliban deal.
Trump’s most significant foreign policy achievement during his first term was the signing of the Abraham Accords in 2020-2021, which aimed to normalise relations between Israel and several Arab states. The agreements, joined by the UAE, Bahrain, and later Morocco and Sudan, emerged from Trump’s dream of a 'deal of the century'. His son-in-law, Jared Kushner, led the effort, initially proposing a plan that would have annexed around 30% of the West Bank, areas with Jewish settlements, while establishing a demilitarised Palestinian state on the remaining land. The Palestinian Authority refused to negotiate under these terms, prompting Israeli Prime Minister Netanyahu to announce his intention to proceed with annexation. To prevent this, the UAE and Bahrain agreed to normalise relations with Israel.
Ben-Gurion University professor Fred Lazin notes that the Abraham Accords were the result of a convergence of key political interests: Trump and Netanyahu were seeking a major diplomatic win ahead of their reelection campaigns; UAE Crown Prince Mohammed bin Zayed wanted to strengthen a Sunni alliance against Iran, position himself as the 'savior' of Palestinians from annexation, and secure US approval to purchase F-35 fighter jets. While the accords represented a promising step, they did not fundamentally reshape Middle East diplomacy, as evidenced by the October 7, 2023, terrorist attack and subsequent events. Plans for other Arab nations, most notably Saudi Arabia, to join the accords have been put on hold, and the agreement remains highly unpopular, including among signatories .
In a sense, this diplomatic breakthrough turned out to be yet another 'first-phase' agreement, followed by deadlock. Trump’s 'arm-twisting' approach yields results that are often declarative and easily reversible.
Nuclear fiasco
Trump’s negotiations with Kim Jong-un (much like his later talks with the Taliban) serve as a striking example of the complete failure of his negotiation strategies. The two leaders met three times, yet the US president was unable to persuade Pyongyang to abandon its nuclear programme or even impose meaningful limits on its scope.
Initially, Trump took an extremely confrontational stance towards the DPRK, threatening Kim with ‘fire and fury like the world has never seen’. However, he failed to anchor these threats effectively. Tensions between the two nations reached their peak in the fall of 2017 when Kim was photographed reviewing nuclear strike plans with his strategic forces chief. As China and Global Affairs editor Katie Stallard has written in a commentary for the Wilson Center, war between Washington and Pyongyang seemed so imminent at the time that then-Secretary of Defense James Mattis slept in his clothes, ready to give the order to shoot down an incoming North Korean missile.
However, Kim abruptly shifted toward de-escalation. He declared that North Korea’s nuclear forces were fully operational and ready to deter an attack, sent his sister to the Winter Olympics in South Korea, and invited Trump to meet 'as soon as possible', hinting at a willingness to engage in partial denuclearisation in exchange for security guarantees and the lifting of sanctions. At this moment, Trump found the prospect of a 'big deal' with Pyongyang highly appealing – offering to lift all sanctions in exchange for North Korea’s abandonment of its military nuclear programme. After their first summit in Singapore in June 2018, both sides issued broad statements, but Trump framed the talks as a major success, lavishing praise on Kim and claiming that the North Korean nuclear threat had been eliminated.
The second summit, held in Hanoi in June 2019, ended in scandal. Kim was only willing to discuss minor concessions regarding nuclear development, leading to an abrupt breakdown in negotiations. The banquet table set for the celebratory dinner remained untouched. Robert Gallucci, a former US envoy to North Korea in the 1990s, told the Los Angeles Times that such high-level summits were doomed from the start: 'You don’t start with summits; you finish with a summit after all the groundwork has been done, and then the two big guys come together to sign something'. Trump’s gamble on direct engagement and the appeal of a 'big deal', which offered North Korea significant economic benefits in exchange for denuclearisation, completely failed.
Following the Hanoi debacle, Trump abandoned the idea of a 'big deal' and attempted to transition to a more traditional step-by-step approach, recalls American diplomat Christopher Hill in Time magazine. Hill, who served as the US envoy for North Korean denuclearisation talks from 2005 to 2009, notes that in 2019, Trump became the first sitting US president to visit North Korea and the Demilitarised Zone – but this yielded no real breakthroughs. Ultimately, Trump’s diplomatic marathon only resulted in North Korea refraining from nuclear and long-range missile tests, releasing a few American detainees, and agreeing to resume the search for the remains of US soldiers killed in the Korean War. Yet, as Hill points out, none of this stopped Trump from calling the negotiations his greatest foreign policy triumph and implying that he deserved the Nobel Peace Prize.
In reality, Kim successfully strung Trump along for more than two years, completely neutralising his initial resolve. This episode highlights the weakness of Trump’s traditional negotiation tactics when confronted with a counterpart who has strategic long-term interests and a willingness to escalate in response to Trump’s hyperbolic rhetoric. Trump’s promises and belief in personal rapport proved ineffective, while his verbal threats were meaningless against an opponent armed with nuclear weapons – no matter how inferior they were compared to Vladimir Putin’s arsenal. Meanwhile, the concessions and assurances Trump has extended to the Kremlin during his new presidential term bear a striking resemblance to the intermediate phase of his relationship with Kim. Once again, Trump is promising to lift sanctions and initiate spectacular economic cooperation, relying on a miraculous breakthrough during a personal meeting.
The Afghan trap
If the failed deal with Kim appears to be a projection of Trump’s negotiation tactics with the Kremlin, then another of his failures is directly relevant to his dealings with Ukraine. In his approach to the Ukrainian issue, Trump is replicating the logic and strategy of his 2020 plan to end the war in Afghanistan, argue former Kabul mayor Shoaib Rahim and director of the Center for European, Russian, and Eurasian Studies at the University of Toronto, Edward Schatz, in a commentary for The Globe and Mail. The Doha agreement signed with the Taliban stipulated the withdrawal of US troops within 14 months. In return, the Taliban promised to prevent terrorist groups from gaining a foothold in Afghanistan and agreed to begin negotiations with the US-backed Afghan government.
By the time Trump entered the White House in 2017, the war in Afghanistan, much like the war in Ukraine today, had reached a stalemate. The Afghan government was unable to exert control over the entire country, while the Taliban could not reclaim power, writes Philip Crowley, former US Assistant Secretary of State, in a piece for the BBC. A year later, Trump grew frustrated with the lack of progress in Afghanistan and declared that the US needed to 'get the hell out’. Sensing Trump’s mood, Secretary of State Mike Pompeo ordered the start of secret negotiations with the Taliban.
Trump’s administration engaged in direct talks with the Taliban, sidelining the official Afghan government, while NATO allies and even US military leaders were informed of the developments only after the fact. Trump’s primary demand was a safe withdrawal of American troops, while the requirement for a ceasefire between the Taliban and the Afghan government was downgraded to a non-binding promise to 'reduce violence'. The demand for a political settlement was reduced to a mere agreement to begin talks, write Rahim and Schatz. As Afghan affairs expert Madiha Afzal notes in a commentary for the Brookings Institution, the agreement, as written, read like a surrender timetable.
At the same time, Trump sought to discredit anyone he saw as an obstacle to the deal – primarily the pro-American Afghan government. Under his pressure, President Ashraf Ghani was forced to send a delegation to negotiate with the Taliban and unconditionally release 5,000 Taliban prisoners. Meanwhile, the Afghan National Army was ordered to take a defensive stance, prohibited from engaging Taliban forces. This soon led to the collapse of government forces and the hasty evacuation of the remaining American troops.
Trump is now following the same playbook in negotiations with Putin, bypassing Ukrainian authorities and NATO allies. Just as he viewed the Afghan government as the main obstacle to his deal, he now sees Ukraine’s government as the primary hindrance, publicly discrediting it and pressuring it into a 'truce' that the opposing side neither seeks nor promises.
Unlike during his first term, Trump’s strategies, and their vulnerabilities, are now well known to those he deals with. His counterparts have learned from his past failures, while Trump continues to replicate his previous approaches almost exactly. His relentless pursuit of a ‘big deal’ that he believes will earn him a Nobel Peace Prize is turning into an obsession, fuelled by repeated failures. At the same time, he increasingly sees his external allies – whose opinions he refuses to consider – and his domestic opponents as the main obstacles standing in his way.