← Back to Library

Weekend update #188: Ukraine reaches out and touches Putin--Twice

Phillips P. O'Brien reframes the week's geopolitical drama not as a diplomatic stalemate, but as a moment where Ukraine successfully seized the psychological and physical initiative from Russia. The piece stands out by connecting seemingly disparate events—a drone strike on an oil terminal and an open letter to Vladimir Putin—into a single, coordinated strategy of humiliation and deterrence. For busy observers tracking the war's trajectory, this analysis cuts through the noise of congressional procedural votes to expose a stark reality: the battlefield is shifting in Ukraine's favor even as political winds in Washington turn hostile.

The Theater of Power in St. Petersburg

O'Brien centers his argument on the dramatic timing of Ukrainian long-range strikes coinciding with the St. Petersburg International Economic Forum (SPIEF). He posits that while world leaders largely shunned the event, attending only the presidents of Uzbekistan and Tanzania, the real story was the shadow cast by a burning oil terminal just miles away. "The Ukrainians were saying to Putin (and the rest of the world) that you cannot protect major facilities of strategic importance in Russia's second city and that you certainly cannot protect public events," O'Brien writes.

Weekend update #188: Ukraine reaches out and touches Putin--Twice

This framing is effective because it highlights a tangible erosion of Russian sovereignty over its own territory, moving beyond abstract front-line maps to the heart of the regime's symbolic capital. The author notes that the attack on the St. Petersburg Oil Terminal was not an isolated incident but part of a broader campaign targeting naval assets in Kronstadt, a location heavy with historical resonance for any regime claiming Soviet continuity. "The historians amongst you will also understand the importance of Kronstadt to a regime that likes to fashion itself as a reborn USSR," he observes, reminding readers that striking there is as much about dismantling imperial mythology as it is about military logistics.

The meaning of the attacks was obvious: no place is safe.

Critics might argue that focusing on high-profile strikes risks overshadowing the grinding attrition of ground warfare or the immense human cost of these escalation cycles. However, O'Brien's point remains that the perception of invulnerability has been broken, which is a critical component of modern asymmetric warfare. The administration in Moscow may dismiss the letter from President Volodymyr Zelensky as "rudeness," but O'Brien interprets it correctly as a calculated power play designed to bypass Washington and speak directly to the Russian populace about their leader's failures.

A Diplomatic Offensive Without American Mediation

The second pillar of O'Brien's analysis is Zelensky's open letter, which he describes not as a genuine bid for negotiation but as a tool for psychological warfare. "Zelensky is taunting Putin and saying to the Russian people that their dictator is destroying them," the author writes. This distinction is vital; it reframes the letter from a failed diplomatic overture into a successful message of defiance intended to fracture the domestic consensus in Russia.

O'Brien argues that this dual approach—military pressure paired with direct communication—signals that Ukraine no longer needs to rely on Western intermediaries to dictate the terms of engagement. "The Ukrainians were not just reaching out and touching Putin, they were making two statements to their own people at the same time," he notes, suggesting that these moves are also meant to bolster domestic morale in Kyiv amidst debates over potential peace deals. The author emphasizes that Ukrainian long-range capabilities have matured to a point where they could strike Moscow on May 9 but chose St. Petersburg instead to maximize political impact. "Look what we can do now and think about how things will develop over the next few months," O'Brien paraphrases the implicit message sent by Kyiv, warning of an increasingly dire future for Russian strategic assets if the conflict continues.

The Paradox of American Policy

The commentary takes a sharp turn to analyze the contradictory behavior of the US government under the current administration. While acknowledging a recent House vote to authorize $8 billion in military financing loans and extend security assistance through 2027, O'Brien dismisses this as largely performative given the political reality. "Even if a bill gets through the Senate... Trump can veto and the bill will go nowhere," he asserts, pointing out that over 90 percent of the Republican party voted against aid.

The author's most provocative claim is that the executive branch is actively undermining Ukraine while publicly claiming to support it. He lists specific actions: canceling Tomahawk missile orders for Germany, extending sanctions waivers on Russian oil, and delaying critical intelligence sharing. "The US government under Trump is doing more and more to help Putin—to the degree that its openness is becoming shocking," O'Brien writes. This section challenges the reader to look past the headlines of legislative victories and examine the operational reality where US policy appears to be facilitating Russian aggression.

The next time you read about a Russian mass attack on Ukrainian civilians, know that the US is helping the Russians in this murderous work.

This stark conclusion forces a reckoning with the human cost of geopolitical maneuvering. By linking US diplomatic and economic concessions directly to continued civilian casualties in Ukraine—citing a recent attack that killed at least 23 people—O'Brien strips away the abstraction of "sanctions waivers" and reveals their lethal consequences. A counterargument worth considering is whether these moves are truly intentional support for Putin or merely the result of bureaucratic inertia and isolationist pressure within the US political system. However, O'Brien's evidence suggests a pattern too consistent to be accidental, painting a picture of an administration that is "doubling down on crushing dissent" while simultaneously eroding Ukraine's defensive capabilities.

Bottom Line

Phillips P. O'Brien delivers a compelling assessment that Ukraine has successfully shifted the war's momentum through precise long-range strikes and bold diplomatic signaling, effectively isolating Putin even as Washington retreats. The piece's greatest strength is its unflinching connection between US policy decisions and their human toll on Ukrainian civilians, yet it risks oversimplifying the internal complexities of American legislative gridlock as purely malicious intent. Readers should watch closely whether Ukraine can sustain this offensive initiative if the flow of Western air defense systems continues to dry up under current executive directives.

Deep Dives

Explore these related deep dives:

  • St. Petersburg International Economic Forum

    Understanding this event's role as a domestic propaganda tool for Putin explains why Ukrainian strikes targeting it during the forum were a calculated psychological blow rather than just an economic disruption.

  • Kronstadt

    The specific vulnerability of this historic fortress near St. Petersburg provides the technical and geographical context for why Ukrainian mid-range strikes there directly threaten Putin's personal security perimeter.

Sources

Weekend update #188: Ukraine reaches out and touches Putin--Twice

by Phillips P. O'Brien · Phillips P. O'Brien · Read full article

Hi All,

I am starting this update with a special announcement. I was going to write more about Ukraine’s mid-range strike campaign today, as it is (finally) getting the coverage it deserves. However, instead of hearing me talk about it, I thought people would like to get the perspective that matters most—the Ukrainian one. So I got in touch with the people at Come Back Alive, and they are going to have two of their best analysts come on a Substack Live here this Wednesday to discuss the mid-range campaign in detail. So do keep free: June 10 at 1730 Ukraine time, 1530 GMT and 1030 EST.

This session will involve not only old friend Mykola Bielieskov (who just did a great video with the Kyiv Independent) but also Vladyslav Urubkov, the Division Lead at CBA’s Military Department. Vlad is a native of Donetsk and was forced out when the Russians invaded and seized the city in 2014. Afterwards he served in the Ukrainian armed forces and now works for CBA.

I cannot think of two better people to discuss the campaign in detail than these two—so please do join if you can.

So, I will not say much new about the mid-range campaign now, but focus instead on the long-range strike campaign as part of a larger main story of the week. That is how the Ukrainians are trying to put pressure directly on Vladimir Putin. There were two fascinating examples of this in the last few days, one military and one diplomatic. The military element was the attack on oil and naval installations not far from St Petersburg, Putin’s home city, just as the St Petersburg International Economic Forum was about to start. The second was the fascinating letter sent directly from Zelensky to Putin expressing a willingness to negotiate directly (in other words without the USA). Both were Ukrainian power plays and deserve comment.

The other major story of the week revolves around the ever closer relationship between the US government and Russia. Though there was a great deal of comment about the vote in the US House on aid to Ukraine, this sadly is a non-event for now. The real story is how the Trump administration is reaching out to Putin more and more.

One quick note before I start the heart of this. I also sent out a piece two days ago about the future ...