Operation Spiderweb
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Operation Spiderweb is the Ukrainian drone attack on Russian strategic bombers at airbases deep inside Russia in June 2025. John Kiriakou's assessment separates admiration for the tradecraft from scepticism about who did it.

The operation

"This was a brilliant operation. Brilliant. Whether you favor the Ukrainians or favor the Russians, a whole lot of planning went into the successful execution of this operation."

What he counts is the logistics rather than the strike. On Ukraine's own account it was eighteen months in the making, which meant smuggling the drones across the border and then "across all 11 time zones" to be prepositioned. "You have to do that with human beings. So this is a clandestine activity, what we at the CIA used to call an operational act. But it's multiple operational acts, to get these things in place and ready to launch, and then have the whole thing commanded from Kyiv. Very, very impressive operation."

Why he does not believe Ukraine acted alone

Volodymyr Zelensky presented the operation as a demonstration of Ukrainian and European capability. Kiriakou disagrees, and grounds it in liaison practice: "the only people who do these kinds of large-scale operations and then don't tell anybody about it are the Israelis. And most of the time the Israelis do inform us, either minutes before the operations are launched or as the operations are being launched."

His conclusion is categorical. "There is no possible scenario by which the Ukrainians didn't either inform the Americans and other Western allies that this operation was in play, or didn't have the Americans and possibly the Brits helping them to do this operation. There are too many moving parts. It's just too complicated. They couldn't do it on their own."

Pressed on what specifically would have been needed, he names imagery and logistical assistance: "you can't do everything yourself. Not when you're a small country at war against a giant nuclear power."

He adds a second, political argument. "If you're the United States providing billions and billions of dollars in aid, then by God, you want to be consulted about these things. You don't want to read about these operations on the front page of the Post or the Times. That's just not the way it's done in that world."

The silence test

The evidence Kiriakou treats as decisive is behavioural. Donald Trump said nothing publicly about the strike, and his press secretary deferred to him when asked.

"His silence tells me that we were in on it. If we had been cut out, he would be furious and maybe even a little bit embarrassed, and he would have been just beating Zelensky about the face and head in the media, and he hasn't been."

What the silence is doing, on his reading, is operational: "it protects the operation, it protects the relationship, you know, sources and methods, as we used to say at the agency." Had the president been cut out and embarrassed, "he would be jumping up and down in front of TV cameras."

The four-point assessment

Speaking days after the strike, Kiriakou set out four separate judgements.

The first is that the bombers were left in the open deliberately. The Russians "decided to allow them to be observable to American satellites, so that the Americans could rest assured that they were not in the process of being used", an adherence to a treaty framework that, he notes, "is not really in effect any more." On that point "the Russians were trying to do the right thing."

The second is arrogance: the aircraft "were so far away from Ukraine that there was no chance, no possibility that the Ukrainians could hit them from Ukraine. And it never occurred to the Russians that the Ukrainians would have instituted this operation."

The third is the execution, which he calls "a colossal" failure on the Russian side precisely because the method was patient: suicide drones put into shipping containers, smuggled into Russia over eighteen months, pre-positioned across the country "as far east as Vladivostok, it doesn't get any further east than that. Russia has eleven time zones; this is the eleventh", and then simply waiting for the moment to launch. He cites press reporting that two billion dollars of aircraft were destroyed.

The fourth is that the timing should have been predictable regardless of the tradecraft: "this is what every country that is at war does on the eve of peace talks. You ratchet up the attacks, you ratchet up the violence, hoping you can get another metre of territory so that you can negotiate it away at the peace talks. What did the Russians think the Ukrainians were going to do, just throw up their hands?"

Not a crime, and a medal

Asked on a Russian network a few days earlier whether the strike had been a criminal act, he said no: "first of all, you're at war, and so it's not a criminal act to bomb a military target. But it was a brilliant act of espionage. Brilliant. Some Ukrainian's going to get a medal for this. It was incredible, gutsy, and incredible in its result."

His one aside about the booking itself records his standing policy on interviews: "I generally say yes to everybody except the Lyndon LaRouche people."

What it achieved

On effect he is unsparing. The demands Russia published for the Istanbul talks were "exactly the same set of demands that they had in the very beginning of the conflict. They haven't budged one inch, not one iota", the Donbas, Crimea, permanent military neutrality for Ukraine, denazification. "So you're right, it didn't have the effects that the Ukrainians, I think, wanted it to have."

What he thinks it did communicate was addressed to Washington rather than Moscow: "this attack was just as much a message to Donald Trump, saying: you can bloviate all you want about ending this war, we're going to keep fighting, and if you're not going to help us, we're going to rely on the Europeans."

See also

- Ukraine as a proxy war
- Volodymyr Zelensky
- Vladimir Putin
- Ukraine Settlement Prediction
