Trump Privately Told Zelensky to Act 'More Boldly' Against Russia. Ukraine Is Now Hitting Crimea Hard.

What Happened

During a June 16 meeting, President Trump privately told President Volodymyr Zelensky to act "more boldly" against Russia, according to a senior Ukrainian official briefed on the discussion who spoke to the Kyiv Independent. The Kyiv Independent, Ukrainska Pravda, and The Mirror all reported the same core claim from the same sourcing chain: unnamed Ukrainian officials familiar with the meeting.

A separate U.S. official told the Kyiv Independent: "President Trump believes in peace through strength."

U.S. officials did NOT confirm that Trump explicitly endorsed Ukrainian strikes inside Russian territory. What they confirmed, according to the Kyiv Independent, is that Trump views strength as the key variable in forcing Putin to negotiate. "Trump told Zelensky to be bolder" and "Trump greenlit strikes on Russia" are two different claims. The sourcing supports the first. The second remains unconfirmed.

ZeroHedge framed the story as a "White House greenlight to bring the war to Russian territory," which goes further than what the primary source — the Kyiv Independent — actually reported. The Kyiv Independent's own phrasing was more careful: officials "stopped short of confirming whether Trump explicitly supports Ukrainian strikes inside Russia."

What Ukraine Is Actually Doing

The operational picture has shifted considerably over the past several weeks. Ukrainian forces struck a railway bridge over the North Crimean Canal near the village of Rozdolne, a structure the Ukrainian Special Operations Forces described as a key logistics route for Russian troops in southern Ukraine, according to The Mirror. A second strike on the same target occurred early Tuesday, June 23, hitting railway repair equipment deployed at the bridge.

Over the weekend, Ukrainian drones also hit an oil storage depot at the Kerch thermal power plant, an electrical substation in western Crimea, and a liquefied natural gas distribution station in Simferopol, according to The Mirror.

Ukrainian Minister of Digital Transformation Mykhailo Fedorov said last week: "It looks like in the nearest time, Crimea will become an island. This could lead to some very unexpected consequences for Russians."

Moscow has not publicly commented on several of these strikes.

The Diplomatic Angle

At the June 16 meeting, Zelensky proposed that Trump host a summit in the United States involving both Zelensky and Putin. "Zelensky suggested to Trump that he bring Putin to America, and that would be perfect," the senior Ukrainian official told the Kyiv Independent. "Donald liked the idea."

U.S. officials familiar with the discussions confirmed to the Kyiv Independent that the proposal was made but cautioned that no such meeting is expected in the "immediate future."

Zelensky laid out his own preconditions on June 17: "I will not travel to Moscow to meet with Putin. We can meet in Turkey, Switzerland, or the Middle East." The Kremlin has continued insisting any meeting happen in Moscow, which Kyiv regards as a deliberate stall.

At the G7 summit, Trump signed a joint declaration reaffirming support for Ukraine, with participating countries stating they are ready to consider granting Ukraine licenses for domestic weapons production, according to Ukrainska Pravda.

The Escalation Question

Critics of escalation argue that Ukraine attacking infrastructure inside Russia and Crimea, with even tacit U.S. backing, carries serious escalation risk with a nuclear-armed adversary. Previous rounds of expanded Western authorization — long-range missiles, F-16s, strikes on Russian territory using Western weapons — did not produce negotiated breakthroughs. They expanded the war's geographic footprint without ending it. The concern is that "peace through strength" is a sound doctrine in most conflicts but carries different calculus when one side holds nuclear weapons and has repeatedly invoked them.

The counterargument, reflected in Trump's own reported framing, is that four-plus years of restraint produced a stalemate, not a settlement. Every freeze in Western pressure corresponded with Russian consolidation of occupied territory, not Russian flexibility. If Putin won't negotiate absent military pain, then military pain is the only lever available.

The Alaska summit between Trump and Putin earlier this year produced no lasting results on Ukraine, according to ZeroHedge. Washington has visibly stepped back from active mediation, with Trump's "I don't mind. Let them deal" comment signaling a posture shift toward Ukrainian agency.

Whether the proposed U.S.-hosted three-way summit ever materializes hinges on one variable the sources cannot answer: whether the Kremlin will accept an invitation framed by Trump rather than one it can simply ignore. U.S. officials told the Kyiv Independent they expect no such meeting "in the immediate future," leaving Ukraine executing a military pressure campaign with apparent U.S. encouragement but without a defined diplomatic endpoint.