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The Planning and Fallout of the Ukrainian Attack on Russia’s Jets

June 5, 2025 By Richard C. Young

LEFT: The President of Ukraine (Volodymyr Zelenskyy) met with the Chairman of the Council of Ministers of the Republic of Poland. February 1, 2022. Photo courtesy of the office of the President of Ukraine. RIGHT: Russian President Vladimir Putin listens as U.S. Secretary of State John Kerry speaks during their bilateral meeting focused on Syria and Ukraine at the Kremlin in Moscow, Russia, on March 24, 2016. [State Department photo/ Public Domain]

The world recently witnessed what, by many accounts, was one of the most impressive feats by an intelligence agency in the history of warfare. Ukraine used smuggled shipping containers full of drones to do significant damage to Russia’s strategic bomber fleet at bases around the country, even deep in its hinterlands. The Wall Street Journal credits Ukraine’s SBU intelligence agency with the attack, writing:

The SBU’s drone attack on Sunday, dubbed Operation Spiderweb, was 18 months in the planning and damaged 41 Russian warplanes at four airfields deep inside Russia, according to the SBU. The agency released fresh drone footage on Wednesday, which showed dozens of drones targeting planes across four Russian airports.

But was SBU solely responsible? At the Future of Freedom Foundation, Jacob G. Hornberger wonders if the U.S. government played a role. He writes:

An important question that is not being asked is: Did Pentagon or CIA officials serve as secret advisors or directors in the drone operation? Since Congress is effectively owned by the U.S. national-security establishment, it’s a question that unfortunately is not going to be asked by any congressional committee. Given the longtime deference to the national-security establishment by the mainstream media, the question is unlikely to come from them either and even if it did, there is no doubt that the Pentagon and CIA would deny it even if they were involved.

Why is the question important? Well, think about it: The U.S. government furnishes weaponry to the Ukrainian government to use against Russian forces. But let’s assume that it goes one step further than that. Let’s assume that it also assists, advises, and directs Ukrainian officials in the use of such weaponry.

That would mean, as a practical matter, that it was the U.S. government that launched that drone attack and was simply using Ukraine as its agent — in order to preserve “plausible deniability.” It would mean, as a practical matter, that it is the U.S. government that is using its weaponry to kill and injure Russian soldiers and destroy Russian armaments, not only in Ukraine but also deep inside Russia.

So what will happen as a result of the attack? At Foreign Policy, Franz-Stefan Gady suggests that the attack is one of history’s most daring, and could trigger a Russian nuclear response if NATO or the United States were involved. He writes:

The raid also illustrated that a non-nuclear power could raid the strategic assets of a nuclear power. The only feasible way for Kyiv to do so safely was to consciously avoid targeting certain assets. The raid’s limitations—both in terms of the targets chosen and the damage inflicted—highlight the constraints imposed by the risk of escalation. Ukraine’s restraint in targeting nuclear-capable bombers and other sensitive infrastructure serves as a reminder that, in an era of nuclear-armed adversaries, even the most successful raids must be carefully calibrated to avoid crossing invisible but potentially disastrous red lines.

Russia’s nuclear doctrine, updated in late 2024, explicitly reserves the right to use nuclear weapons in response to attacks on its territory by a non-nuclear state that is backed by a nuclear-armed one. Although Ukraine is not directly backed in any strict sense by a nuclear state, the presence of NATO support and the risk of Western intervention looms large in Russian strategic thinking. The Kremlin’s repeated nuclear threats—including tactical strikes, high-altitude detonations, and missiles fired on European capitals—have been a constant feature of the war, even as most of the Kremlin’s supposed red lines have been crossed without triggering nuclear use.

This dynamic creates a paradox: the more effective Ukraine’s raids, the greater the risk of a disproportionate escalation by Russia. For some observers in the West, the fear of a severe Russian reaction almost overshadows the operational success of the raid itself. This plays into a culture of Western self-deterrence in response to Russian threats, whereby Russia actively uses nuclear and conventional saber-rattling not merely in a neutral strategic context, but also as a deliberate tool to manage and constrain Western behavior.

Elsewhere in Foreign Policy, John Haltiwanger interviews George Beebe, former director of Russia analysis at the CIA, who thinks that Russia’s response will depend on the posture struck by American President Donald Trump. Beebe suggests that Trump can “defuse” the situation, responding:

It is embarrassing for Putin. Clearly, there were security lapses on the Russian side that allowed this to happen. Border security, for example. The Ukrainians brought these drones deep into Russian territory by sending them across the Russian border. Russian border inspectors failed to catch this, and that is an embarrassing lapse.

This does put pressure on Putin to respond in some way, and there will be a lot of his advisors that say, “We can’t afford not to respond, because if we don’t, this will just cement this impression that Ukraine and its allies in the West can just continue to push across all Russian red lines, and now they’ve crossed our nuclear security red line, which was clearly articulated in the revised nuclear-use doctrine. So, we can’t afford to simply ignore this.” That’s what they will argue.

Now, Putin is the ultimate decision-maker, and whether he agrees with that or not, we will have to see. But it’s very much in America’s interest to defuse this situation, because this is one that could escalate.

And it appears that Putin will respond to Ukraine’s attack. President Trump spoke with Putin after the attack, and during the conversation the Russian president told Trump that he would respond. Trump wrote of the call:

I just finished speaking, by telephone, with President Vladimir Putin, of Russia. The call lasted approximately one hour and 15 minutes. We discussed the attack on Russia’s docked airplanes, by Ukraine, and also various other attacks that have been taking place by both sides. It was a good conversation, but not a conversation that will lead to immediate Peace. President Putin did say, and very strongly, that he will have to respond to the recent attack on the airfields.

What will be his response? Beebe suggested to Foreign Policy that it could be an attack on Ukraine’s command and control bunkers, and that if such an attack happened, the United States may feel obligated to get more involved.

It would not necessarily escalate immediately into a direct confrontation between the United States and Russia. But it’s not hard to imagine a set of circumstances where Putin takes quite forceful action against Ukraine. And one example might be the use of these Oreshnik advanced missiles, which have maneuvering warheads with the ability to strike deep underground facilities in Ukraine, to go after Ukraine’s command and control capabilities, which I believe are located in hardened, deep underground structures, but may well be vulnerable to Russian strikes.

Now, if Russia were to do that and were to create the kind of destruction in and around Kyiv that it’s capable of conducting, would the United States simply step back and say, “Not our problem”? Would Trump be able politically to say, “Oh, well, not our battle, not my war. This is between Russia and Ukraine”?

I think he would be under tremendous political pressure to do something in response. And that is a dangerous situation. No question.

 

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Richard C. Young
Richard C. Young
Richard C. Young is the editor of Young's World Money Forecast, and a contributing editor to both Richardcyoung.com and Youngresearch.com.
Richard C. Young
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