Former President Donald Trump has taken a significantly tougher stance on Russia’s war in Ukraine, which has surprised both supporters and detractors. This is a far cry from his prior stance of disinterest and distance. Trump, who was once a strong opponent of American engagement in the war, is currently in the news for asking Ukrainian President Volodymyr Zelenskyy if Ukraine could launch an attack inside Russia, specifically against Moscow and St. Petersburg, if it were equipped with the necessary weapons.

The change may seem abrupt to older Americans who are watching this war from a distance. Trump, after all, has long espoused the “America First” philosophy, publicly challenging U.S. financial and military assistance to Ukraine and denouncing NATO’s management of the war. However, the former president’s tone is rapidly shifting as the war continues unabated and tensions in Eastern Europe rise.

A Difficult Partnership with Ukraine

Trump’s relationship with Ukraine has never been simple. He frequently criticized the United States’ involvement in the war during his 2024 presidential campaign, claiming that the billions of dollars in aid would be better used domestically.

Trump maintained his icy posture even in the first few months after taking office again. He claimed that Ukraine, not Russia, was the one who started the conflict, portraying Ukraine as the aggressor rather than the victim. Additionally, he raised doubts about the validity of extending military assistance, which infuriated lawmakers from all parties.

Following a White House meeting with Zelenskyy in February, where the Ukrainian president allegedly left with little guarantee that more assistance would be forthcoming, the tense relationship reached yet another low point. That was the end of the conversation for many.

However, something has obviously changed in the last week.

An Unexpected Change in Approach — and Tone

Trump shocked the world on Monday when he threatened to impose 100% “secondary tariffs” on nations that still do business with Russia if a peace agreement wasn’t reached within 50 days.

Trump declared, “We’re going to be implementing very severe tariffs because we’re very, very unhappy with them.” tariffs at roughly 100%. They are referred to as secondary tariffs.

Additionally, he expressed his dissatisfaction with Russian President Vladimir Putin, pointing out that he has refused to engage in ceasefire negotiations. Trump made it clear that “we’re going to be doing secondary tariffs” if an agreement is not reached by September.

The new position is a 180-degree turnabout for a man who previously questioned Ukraine’s integrity and praised Putin’s strength.

Trump Approves Billions for Military Hardware

Trump also announced a fresh round of military equipment shipments to Ukraine, albeit with a politically shrewd arrangement, in addition to economic threats. Trump claims that American defense manufacturers will supply the weapons, which will be delivered through NATO and paid for by European allies, rather than sending U.S. taxpayer-funded weapons directly.

This tactic enables Trump to uphold his “America First” stance while simultaneously intensifying his backing for Ukraine, especially given NATO’s growing concern over the war’s regional threat.

But the move is only one aspect of the story.

Behind Closed Doors: Did Trump Support Moscow Attacks?

Trump reportedly asked Ukrainian President Zelenskyy if he could attack Moscow and St. Petersburg — provided the United States provided long-range weapons, according to a shocking report from the Financial Times that was later confirmed by The Washington Post.

According to unnamed people with knowledge of a July 4 phone conversation between the two leaders, Trump inquired:

“Can you hit Moscow, Volodymyr? Are you able to visit St. Petersburg as well?

According to reports, Zelenskyy replied:

Yes, without a doubt. If you give us the weapons, we can.

In the alleged conversation, Trump also admitted to Zelenskyy that he had a “bad” conversation with Putin the day before.

If accurate, the conversation shows a significant increase in Trump’s readiness to take on Russia directly, even pushing Ukraine to do so. Such a move would put the United States at the center of a foreign war once more and would signal a significant increase in tensions around the world.

“No, He Should Not Target Moscow,” Trump denied.

Trump refuted the claim a few days after it was reported.

On July 15, Trump attempted to retract the leaked conversation by saying, “No, he should not target Moscow.”

The harm — or clarity — had already been done, even though the denial was obvious. The public was left to wonder where Trump’s Ukraine policy stands and to reconcile his past hesitancy with his current aggression.

Between “America First” and “Russia Must Feel Pain”

The Financial Times report’s description of Trump’s approach—to “make them [the Russians] feel the pain”—may have been more illuminating than any quote.

It’s a strong statement that suggests Trump no longer believes that diplomacy is the only option. It also shows how, in spite of his public personas, Trump might be changing his approach to world leadership from isolationism to more interventionist positions, provided that doing so advances his objectives.

Older voters who remember the Cold War era and who value strength and decisive action in foreign policy may find this new tone—more militant, more commanding—appealing. However, it also brings up important questions regarding escalation and the United States’ long-term involvement in the war.

An Old Conflict Enters a New Chapter

It’s unclear if Trump’s change is political, strategic, or personal. He is no longer taking a passive approach to Russia and Ukraine, that much is clear. He’s speaking more confidently, making more direct threats against Russia, and lending Zelenskyy more support, albeit in private.

Additionally, older Americans watching from home may experience a mixture of anxiety and déjà vu as the war in Ukraine rages on. The stakes are getting higher. The argument is getting heated. And at the heart of it all once more is one of the most divisive leaders in the world.