The likelihood of such a meeting hinges on several key conditions. First, both Putin and Zelenskyy would need to perceive Trump as a neutral and effective broker. This is a significant challenge. While Trump has expressed admiration for Putin in the past, a dynamic that could be seen as an advantage by Moscow, it is a major source of apprehension for Kyiv. Ukraine's leadership has consistently sought assurances of strong Western support, and a mediator perceived as sympathetic to Russia's interests could undermine their position.
Second, the political context within the United States is critical. A Trump-led mediation effort would likely face skepticism and resistance from parts of the US political establishment, which could complicate diplomatic efforts. While the President holds significant foreign policy power, the success of any deal would require broader international buy-in, including from European allies who have been crucial in supporting Ukraine.
Third, the substantive demands of both sides remain a major hurdle. Russia's core objective is to secure its territorial gains and prevent Ukraine from joining NATO, while Ukraine's main demand is the full restoration of its sovereignty and territorial integrity. A mediator, even one with a unique political style, cannot simply bypass these fundamental disagreements. A meeting could only be probable if both leaders believe a new mediator offers a pathway to a deal that meets at least some of their core demands, or if their current positions become unsustainable.
In conclusion, while a meeting between Putin and Zelenskyy arranged by Trump is not impossible, its probability remains low in the short term. The deep-seated distrust and conflicting objectives of the two nations, coupled with the complexities of international diplomacy and Trump's own political history, create significant barriers. A successful mediation would require not just a meeting, but a dramatic shift in the strategic calculus of all parties involved.