The High-Stakes Gamble: Zelenskyy‘s Looming Meeting with Trump and the Future of Ukraine
The fate of Ukraine hangs in the balance,not solely on the battlefield,but increasingly on the unpredictable dynamics of a potential deal brokered by former President Donald Trump. As Ukrainian President Volodymyr Zelenskyy prepares for a crucial meeting with Trump, the outcome is far from certain, resting heavily on the former President’s mercurial mood and evolving vision for resolving the conflict. This isn’t simply a negotiation; it’s a high-stakes gamble with potentially devastating consequences for ukraine,and a test of whether a path to peace can be forged through diplomacy or will succumb to the pressures of appeasement.
For over a year, the war in Ukraine has been a defining geopolitical crisis. Now, with Trump actively pursuing a resolution, the situation has entered a new, and arguably more precarious, phase. as a long-time observer of international conflict and U.S. foreign policy, I’ve seen firsthand how personality and political calculation can dramatically alter the course of events. And in this instance, those factors are paramount.
The Trump Factor: From disengagement to Peacemaker?
Trump’s approach to the conflict has been, to put it mildly, inconsistent. Initially, there were signals of disengagement, with the former President suggesting he would allow the two countries to “kill each other,” effectively washing his hands of the situation. This stance,while shocking to manny,aligned with his long-held skepticism of foreign entanglements.
However, that narrative has shifted. Bolstered by a recent diplomatic success in securing a ceasefire agreement in gaza, Trump has tasked his close associate, Steve Witkoff, with securing a deal in Ukraine before Thanksgiving. this pivot,driven by a desire to be seen as a peacemaker,is a classic Trump maneuver – leveraging perceived success to build momentum and project strength.
But the initial framework for a peace deal, a 28-point plan reportedly developed in consultation with russian counterparts, raised serious concerns. Analysts, including some within the Republican party, noted striking similarities to the agreements reached during Trump’s 2019 summit with Vladimir Putin in Alaska – a meeting widely perceived as a diplomatic win for russia. Senator Mitch McConnell succinctly captured the prevailing anxiety, warning against the dangers of “pressuring the victim and appeasing the aggressor.”
Refining the Plan: Progress in Geneva, But Lingering Doubts
Recent talks in Geneva, however, appear to have yielded some progress. Secretary of State Marco Rubio hailed “tremendous progress” in addressing Ukraine’s concerns with the original plan. This echoes a similar shift observed after the June NATO summit, where Trump expressed “disappointment” with putin’s lack of follow-through on previous commitments.
This recalibration isn’t necessarily a sign of genuine commitment to Ukraine’s sovereignty. Instead, it reflects a pragmatic calculation within Trump’s orbit: a recognition that a completely pro-Russian solution is politically untenable, and that a semblance of Ukrainian buy-in is necessary to present the deal as a legitimate peace agreement.
Ukraine’s Weakening position: A Critical Leverage Point
Underlying this shift is a growing assessment within the Trump administration that Ukraine is in a substantially weakened position. As international affairs professor Michael Desch of Notre Dame points out, Ukraine is facing mounting challenges: declining troop morale, increasing desertions, and a burgeoning corruption scandal.
More fundamentally, there’s a belief that Ukraine is unlikely to regain control of the Donbas region and faces the prospect of further territorial losses. This perception of vulnerability, coupled with dwindling Western support, gives the Trump team notable leverage. “I don’t know what chips Ukraine has at this point,” Desch observes, “and I think the Trump folks know that.”
the Core Dilemma: Territorial Concessions and “Abject Surrender”
The most contentious issue remains territorial concessions.An initial proposal for a demilitarized zone ceded to Russia – a long-held Russian objective - appears to have been dropped. However, the specifics of any potential territorial adjustments remain unclear.
This is where Zelenskyy faces an impractical balancing act. As Columbia University’s Rajan Menon aptly notes, the ukrainian President must demonstrate a willingness to engage with a U.S. peace plan while together resisting any provisions that would constitute “abject surrender.” The success of the upcoming meeting hinges on Zelenskyy’s ability to navigate this treacherous terrain.
What’s at Stake?
The stakes are immense.A peace deal that unduly favors

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