However, the question remains: is this a straightforward task? The success of their discussions hinges on whether both leaders can agree to terms. Trump has cultivated an image as a master dealmaker, but Putin’s extensive experience, political acumen, and strategic maneuvering position him as a more seasoned player. Therefore, convincing Putin to accept Trump’s terms will not be easy. To understand who might have the upper hand, one can examine recent examples.

Trump’s past dealings have been marked by controversy and failures. For example, consider North Korea. Trump expressed his readiness to re-engage in discussions with Kim Jong Un to achieve the denuclearization of North Korea. However, Kim Jong Un’s influential sister made it clear that the U.S. must acknowledge North Korea’s status as a nuclear-armed nation, also warning that any dialogue would not lead to disarmament. In the case of Iran, Trump withdrew from the Barack Obama-era nuclear agreement during his first term, but did not present a new, enduring agreement. During his second term, he issued Iran a deadline to comply with the nuclear deal’s terms; however, neither Iran nor Israel conceded, and this deadlock resulted in a 12-day war. Iran remains steadfast in its stance to this day.

Trump’s failures extended to Brazil. He attempted to bring Brazil in line with his policies, but failed. He imposed a heavy tariff of up to 50% on Brazil to protect his old friend and former President Bolsonaro from lawsuits, but the current Brazilian President, Lula da Silva, did not yield. The result was a deterioration in relations between the two countries. These incidents demonstrate that Trump’s deal-making tactics often garner initial attention but frequently become entangled or remain unfinished.

Vladimir Putin’s approach to dealmaking is distinctly different from Donald Trump’s. He is considered a leader who prioritizes action over rhetoric. According to experts, Putin negotiates agreements within a highly controlled environment. A recent example of this is his relationship with Kim Jong Un, the North Korean dictator.

Kim Jong Un is considered one of the most isolated and untrustworthy leaders in the world, but Putin has gradually, and without fanfare, made Kim a close ally. North Korea has even sent its soldiers to assist Russia in the war in Ukraine. In essence, while Trump’s deals often remain within the realm of media headlines and initial buzz, Putin’s deals are often solidified behind the scenes and have a lasting impact for years.