Cliff May: Negotiated Settlement in Ukraine Requires Real Pressure on Russia

Debate over the future of the war in Ukraine intensified this week after Vice President JD Vance suggested the United States should act as a mediator between Kyiv and Moscow, framing negotiations as the inevitable way most wars end. On Chicago’s Morning Answer, foreign policy analyst Cliff May countered that view, arguing history shows that wars often conclude with victory and unconditional surrender—not compromise.

May, president of the Foundation for Defense of Democracies and a columnist for the Washington Times, said President Trump is right to want to end the war but warned that any settlement requires leverage. “Putin is not going to make concessions unless there is pressure,” he explained, noting that Russian forces have relied on terror tactics against civilian targets while struggling to advance militarily.

One proposal gaining attention, from historian Stephen Kotkin, includes confiscating $300 billion in Russian deposits held in European banks, expelling Gazprombank from international financial systems, and pushing India and European nations to stop purchasing Russian oil and gas. Kotkin also suggested attempting to reduce China’s support for Moscow through a side deal with Beijing. May described these measures as “worth exploring and probably worth doing,” though he cautioned that Beijing could try to extract unacceptable concessions over Taiwan.

May emphasized that Ukraine remains an important asset to Western security, providing battlefield insights that have shaped U.S. defense investments. But he warned that ceding Ukraine’s fortified eastern cities—the so-called “fortress belt”—would make Kyiv far more vulnerable to future Russian attacks. He also dismissed Moscow’s call for “security guarantees” that include Russian or Chinese involvement as an obvious ploy.

According to May, Ukraine’s immediate need is more munitions and long-range weapons, ideally supplied through European allies purchasing from U.S. stockpiles. He argued that sustaining Ukraine’s defense not only pressures Russia but also strengthens the American defense industrial base.

As May summarized, Putin may eventually declare victory with Crimea and the land bridge he already controls, but only if he faces consequences strong enough to compel him. “Without pressure,” he said, “the lion has no reason to sit down with the lamb.”

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