Trump Envoy Warns of Escalating Risks After Ukraine Hits Russian Bombers
June 2025 – In a rapidly escalating chapter of the Ukraine-Russia war, Keith Kellogg, a top envoy for former U.S. President Donald Trump, issued a stark warning that "risk levels are going way up" following a bold Ukrainian drone offensive targeting strategic Russian bombers.
Ukrainian Operation: "Spider’s Web" Strikes Deep
On June 1, 2025, Ukraine launched Operation Spider’s Web, using over 100 drones to strike five Russian airbases — Olenya, Dyagilevo, Ivanovo, Belaya, and Ukreinika. These sites house long-range strategic bombers like the Tu-95 and Tu-22M3. The strikes reportedly disabled or destroyed more than 40 aircraft, a crippling blow to Russia’s nuclear air deterrent capabilities.
This dramatic escalation was aimed at showcasing Ukraine's ability to strike deep into Russian territory, shaking Moscow’s confidence and military posture. Experts liken the attack to a "chess master’s trap" — bold, strategic, and high-stakes.
Trump’s Camp Voices Concern
Keith Kellogg, speaking to Reuters, said the operation represents a potential tipping point in the conflict. "You’re striking assets that are part of Russia’s nuclear triad. It’s not just a battlefield escalation, it’s a strategic one," he warned.
Impacts on Russian Military Strategy
The targeted bombers, many of which are relics of the Soviet era, are difficult and expensive to replace. Russia’s ability to project power across the region and respond to NATO’s eastern expansion has taken a visible hit. As noted in The Washington Post, this marks one of Ukraine’s most consequential strikes yet.
Message to the West
Ukraine’s leadership is signaling that it will continue to confront Russian forces directly, even without increased Western military aid. The strikes come amid growing fatigue in U.S. and European capitals over long-term assistance to Kyiv. Still, the symbolic success of Operation Spider’s Web may help reinvigorate calls for renewed Western support.
Trump’s Position in a Changing Landscape
While the Biden administration has taken a measured approach, former President Donald Trump has indicated skepticism toward U.S. involvement in the war. However, Kellogg’s statements suggest that even within Trump’s camp, there is recognition of how dangerously the stakes have risen.
For more context on Trump's stance on foreign conflicts, see our article on Trump’s foreign policy.
Global Fallout: Is Deterrence Breaking Down?
Analysts warn that the targeting of strategic bombers could breach unspoken red lines in wartime conduct. Russia has already ramped up missile attacks on Kyiv in retaliation. There are growing fears that if these escalations continue unchecked, it may lead to direct confrontations with NATO or even risk the use of tactical nuclear weapons.
Conclusion
The recent drone strikes mark a pivotal shift in the conflict’s trajectory. With rising tensions and shifting power balances, diplomatic solutions become increasingly urgent. But as it stands, the world inches closer to a more dangerous and volatile phase of the Ukraine-Russia war.
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