Zelenskyy’s Playbook for Dealing with Trump: Gratitude Meets Hard-Nosed Bargaining

Ukraine’s Approach to U.S. Relations

According to Главком: At the 18th Kyiv Security Forum, Stephen Sestanovich, a senior fellow at the Council on Foreign Relations, outlined Ukraine’s strategy for engaging U.S. President Donald Trump. The approach combines public expressions of thanks with pragmatic deal-making. By traveling to the Middle East, Ukrainian President Volodymyr Zelenskyy signals to Washington just how influential Kyiv can be. Sestanovich stressed that the “America First” slogan does not mean abandoning allies, noting that Republicans and the American public continue to support NATO.

Inside the White House Talks

During negotiations at the White House on August 18, 2025, Zelenskyy thanked Donald Trump and the United States more than ten times. Sestanovich explained that Zelenskyy and his team have adopted a dual strategy for working with Trump:

• First, say thank you as often as possible.
• Second, follow up with a proposal: ‘Now let’s negotiate-let’s discuss the details of a minerals deal or anything else,’ the expert noted.

Beyond that, Sestanovich highlighted that Zelenskyy is trying to convey: ‘I’m not someone who just says thank you. I’m someone you need to take seriously. That has proven to be a fairly effective message. It shows he holds cards, can advance his own interests, and that gets Trump’s attention.’ In this way, the Ukrainian president’s strategy aims to strengthen the country’s position on the global stage, particularly in its relationship with the United States.

This strategy reflects Ukraine’s drive to more actively involve the U.S. in its interests, especially in areas of economic cooperation and security. Pairing public gratitude with concrete, pragmatic offers could be a key step in deepening bilateral ties, particularly amid global political challenges.

While Zelenskyy's strategy focuses on engaging with Trump through gratitude and negotiation, his cautionary stance on Trump's dealings with Putin reveals the complexities of Ukraine's diplomatic landscape. Understanding these dynamics is crucial as they shape not only Ukraine's foreign relations but also the broader geopolitical climate.