Zelenskyy Had The Cards

A surprise attack, planned and devastatingly launched from inside Russian territory, has reset the board in the Ukraine / Russia war and beyond

Image of aircraft hit by drone attacks, from UAF video

Ukraine just pulled off a stunning military operation, its success matched only by its sheer audacity. In one move, Zelenskyy reset the board not only with Russia but the entire Western alliance. He and his team instantly redefined modern warfare and shifted global thinking overnight on the question of nuclear deterrence.

For 18 months, Zelenskyy kept the mission secret, even from—or perhaps particularly from—the Trump White House. He personally oversaw what became known as Operation Spiderweb, a secret plan to strike a devastating blow to Russia’s air power, particularly its long range bombers that have been raining hell down upon Kyiv in the form of cruise missiles.

The Ukrainians decided back then they wouldn’t attack using conventional means. Knowing they were outmatched in firepower, the Ukrainians decided to fight asymmetrically, and to use the arrogance and false confidence of the Russians against them.

The result was a devastating blow to Russia’s air force. Some are calling it Russia’s “Pearl Harbor” moment. This is the story of how it went down.

Russian defense plans never accounted for this

There’s an old saying that it’s better to shoot the archer than to try and shoot down the arrows. But for years, the best Ukraine could do against a constant stream of missiles, many fired from Russian long range bombers too far away to target, was to try and shoot down the “arrows” mid-flight. Many still got through Kyiv’s defenses, with devastating and often deadly results.

Russia knew that Ukraine would love to strike its bombers at their most vulnerable, meaning parked on the ground. But the airbases that hosted them were hundreds and even thousands of miles away from Ukraine, too far even for longer range missiles to reach. The sites included

• The Olenya Air Base in the Murmansk Region

• The Belaya Air Base in the Irkutsk Region

• The Ivanovo Severny Air Base in the Ivanovo Region

• The Dyagilevo Air Base in the Ryazan Region

But could Ukraine somehow strike these bases with drones? As Dara Massicot, a Russian defense expert and senior fellow at the Carnegie Endowment for International Peace, noted, the Russians had gamed out and prepared for what a drone attack would look like:

Russia’s VKS and the General Staff have been studying drone threats to bases for a few years and have implemented various air defense, [Early Warning] and reconnaissance modifications, assuming launches from Ukraine.

It’s that last part they got wrong. The Russians never anticipated that the call would be coming from inside the house. Specifically, Ukraine’s operation used trucks inside of Russia to get close to the air bases and attack before anyone knew what was happening.

Russia also made the fatal mistake of not protecting its fleet using hardened shelters, leaving them out in the open and vulnerable to drone attack. (This is ironically in part because of the mutual inspection requirements of the START treaties, but there’s no specific requirement to actually leave the bombers completely exposed.)

For example, here’s a satellite image of the Belaya Air Base from before the attack showing multiple vulnerable crafts:

I’m no military expert (though I did study arms control at university), but those do look like easy targets for drones, provided you can get close enough.

Operation Spiderweb

Hats off to the Chief of the Security Service of Ukraine (SBU), Lieutenant General Vasyl Malyuk. Together with Zelenskyy, they managed to keep an entire and quite massive operation under complete wraps until they sprung it yesterday.

Image courtesy of Ukrainian Armed Forces

The SBU published certain details of its planning. I’ll get to why they would choose to publicly disclose the details of their operation in a bit. The mission involved complex logistics.

First, drones were smuggled into Russian territory and held in a warehouse in Chelyabinsk near the border with Kazakhstan.

Some assembly of the drones apparently took place inside Russia. (Certain details blurred out for security reasons.)

Here’s how one of these looks up close.

Then, mobile wooden sheds were brought in, and the drones were hidden under the roofs of the sheds.

The sheds were closed up and then loaded onto cargo trucks.

The Ukrainians cleverly used Russian drivers to transport the trucks to locations near to the target air bases. The drivers had no idea what they were carrying or whom they were carrying the cargo for. At the designated time, the roofs opened remotely and the drones launched, targeting military airfields and aircraft.

Because these were operated remotely, there is footage of the drones locating and striking their targets, guided by “First Person View”—which gives them their name, “FPV” drones. This video was released by Ukrainian officials.

After the attacks were over, reports indicated that some 40 Russian planes had been destroyed or badly damaged. That’s around one third of their bomber fleet.

Global repercussions

The bombers struck and destroyed by Ukraine as a result of Operation Spiderweb aren’t just conventional bombers used on the battlefield in Ukraine. They also comprise a key leg of Russia’s strategic nuclear arsenal. Losing a third of this force overnight, and having to scramble to protect the remaining bombers, puts Russia in the position of being unable to respond fully in the event of a nuclear escalation.

Russia’s intercontinental ballistic missiles are old and rusty, and it’s unclear how many still could launch and strike their targets. (We of course hope to never find out.) Submarines can be tracked and destroyed, and their nuclear missiles are similarly untested and old. So the relatively secure, at least until now, third leg of Russia’s strategic nuclear force—its long range nuclear bombers—forms a critical operational component. Without it, Russia doesn’t really have a nuclear deterrence because it cannot assure destruction of the other side.

The fact that simple drones could wipe out a third of Russia’s bomber fleet in a single day raise serious questions about the long term viability of its nuclear arsenal. The U.S. and Russia will now scramble to reassess vulnerabilities in the age of drone warfare. In the meantime, the rules of M.A.D.—mutually assured destruction—may not fully apply. And that means we are in a highly destabilized moment.

Here’s another eye-popping fact: These FPV drones cost only around $500 or $600 each, but the damage done to the Russian bomber fleet is estimated at around $7 billion. Many of these are no longer in production and can’t be replaced.

We’ve truly entered a new age of asymmetrical warfare.

Psychological warfare

Ukraine revealed the operational plan of Spiderweb, but what had happened was already abundantly clear from private footage taken by Russian citizens who saw the drones take off from the tops of cargo trucks and deliver their explosives to Russian air bases.

It was such a low tech plan that the very idea that it could happen has upended Russian society. The fact that an entire warehouse of attack drones was housed inside Russia has Russian military bloggers more than dismayed. It implies the SBU can operate with impunity inside of Russian territory. As one commentator noted on Telegram, “Drones made from ‘shit and sticks’ are taking out an element of the nuclear triad. A complete failure of the Russian structures responsible for protecting strategic aviation airfields.”

Trucks are now being stopped everywhere and searched, grinding transportation to a halt. And Russian political commentators appear stunned, grappling with the idea that they simply cannot predict the next clever attack.

To underscore this point, Zelenskyy taunted Russia by claiming, “The ‘office’ of our operation on Russian territory was located directly next to an FSB headquarters in one of their regions.”

And after all, if drones carried by unwitting Russian haulers can reach as far as Murmansk near Finland, and operations can happen right under the nose of the FSB, then nothing and no one is safe anywhere in Russia.

Zelenskyy no doubt wants that made clear, given how that is how Ukrainians have lived for over three years under constant barrage from Russia. Unlike that country, however, Ukraine struck only legitimate military targets inside of Russia. It did not target civilian infrastructure. But it certainly now could.

On the eve of peace talks

In what is likely an intentional jab in Putin’s eye, the attacks yesterday preceded peace talks between the parties in Istanbul, which began today. The Russians arrived to a swarm of press asking them about the attacks upon the air fleet, but the Russian delegation (which does not include Putin) was in no mood to talk. “Tomorrow, tomorrow,” Vladimir Medinsky, a top aide to Putin, kept repeating like a mantra in lieu of answering reporters’ questions.

After the attack, Zelenskyy had a message for the people of Ukraine, and also for the Russians:

Ukraine is defending itself, and rightly so – we are doing everything to make Russia feel the need to end this war. Russia started this war, Russia must end it.

It was not long ago that Donald Trump berated Zelenskyy in the Oval Office, sneering that he had “no cards” and attempting to bully him into accepting intolerable conditions for an end to the conflict. But Trump vastly underestimated Zelenskyy. The Ukrainian president knew about Operation Spiderweb at that time, but he kept what cards he did have close and chose not to disclose any of it to the White House or the Pentagon.

The details might have made their way onto an unsecured Signal chat, after all.

Yesterday, Zelenskyy finally showed those cards and demonstrated the correct way to negotiate with a brutal dictator like Putin.