Trump’s Shift on Ukraine: From Reluctance to Retaliation?

Former President Donald Trump, long known for his skepticism toward U.S. involvement in Ukraine’s war with Russia, appears to be undergoing a surprising shift in tone and strategy. After months of maintaining a stance focused on “America First” and downplaying Ukraine’s need for support, Trump is now reportedly considering an aggressive pivot—one that includes supplying advanced weaponry and even, according to some sources, encouraging Ukrainian strikes deep into Russian territory.

Throughout his 2024 presidential campaign, Trump often criticized the Biden administration’s support for Ukraine, portraying it as wasteful and misaligned with American interests. At rallies and debates, he frequently questioned the justification for the conflict and even suggested that Ukraine, not Russia, had escalated tensions.

His relationship with Ukrainian President Volodymyr Zelenskyy was marked by distance and uncertainty. A much-publicized meeting at the White House in February offered little clarity and seemed to reinforce Trump’s reluctance to deepen U.S. military involvement.

But in a sharp turnaround, Trump announced earlier this week that his administration would authorize the delivery of billions of dollars’ worth of U.S.-made military equipment to Ukraine. The weapons would be purchased by European allies and sent to NATO stockpiles before reaching Ukrainian forces—a move designed to bypass direct U.S. taxpayer funding while still reinforcing the war effort.

The announcement came alongside a threat directed squarely at Russia. Speaking to reporters on Monday, Trump warned that unless Russian President Vladimir Putin agreed to a ceasefire within 50 days, the United States would impose “secondary tariffs” on countries continuing to trade with Russia—tariffs that could reach as high as 100%.

“We’re very disappointed that Putin still hasn’t agreed to a deal,” Trump said. “If there’s no agreement by the deadline, we’re going to introduce very strong tariffs on anyone doing business with them.”

But what truly caught international attention was a new report claiming Trump privately encouraged Ukraine to take more direct action against Russia—including strikes within Russian borders.

According to the Financial Times and The Washington Post, both citing anonymous sources familiar with the matter, Trump had a phone call with President Zelenskyy on July 4 in which he allegedly asked if Ukraine could launch drone strikes on major Russian cities, including Moscow and St. Petersburg, if provided with long-range weaponry.

“Volodymyr, can you hit Moscow?” Trump reportedly asked during the call. “Can you hit St. Petersburg too?”

The supposed suggestion was described by the sources as part of a strategy to “make them feel the pain,” with the intent of pressuring Russia into serious negotiations. One source claimed Trump told Zelenskyy he had spoken with Putin the day prior and described their conversation as “bad.”

Zelenskyy reportedly responded that Ukraine was capable of hitting targets inside Russia—but only if supplied with the appropriate weapons systems.

“Absolutely,” he said, according to the sources. “We can if you give us the weapons.”

The reports quickly ignited controversy. While the alleged phone call has not been officially confirmed by either government, Trump issued a public statement on July 15 denying the suggestion that he had encouraged Ukraine to strike Moscow.

“No, he should not target Moscow,” Trump stated. “That’s not what I said, and I do not support long-range attacks on Russian cities.”

Still, the former president’s evolving stance suggests a significant recalibration of his approach to foreign policy, particularly toward Eastern Europe. His recent remarks and proposed measures reflect a more forceful posture toward Russia—one that stands in stark contrast to his earlier rhetoric, which many critics claimed was overly accommodating to Vladimir Putin.

The apparent shift may be political, strategic, or both. With the 2026 elections looming and U.S. public opinion increasingly divided on foreign military aid, Trump may be seeking to balance his nationalist platform with growing calls for international deterrence.

Meanwhile, Zelenskyy’s administration has remained largely quiet on the reported exchange, though Ukrainian officials have consistently emphasized their desire for advanced weaponry to defend against Russian aggression. If Trump’s new promises materialize, they could mark a significant boost to Ukraine’s war capabilities—and possibly a turning point in the conflict.

Whether this change of heart is temporary or part of a broader strategy remains to be seen. But one thing is clear: Donald Trump’s stance on Ukraine is no longer as predictable as it once was.