Inside Operation Spider’s Web

Summary

Summary of "Inside Operation Spider’s Web" – The Daily

Podcast Information:

• Title: The Daily
• Host/Author: The New York Times
• Episode: Inside Operation Spider’s Web
• Release Date: June 4, 2025
• Description: A deep dive into Operation Spider’s Web, an innovative Ukrainian military strike against Russian airbases using low-cost drones, analyzed by seasoned New York Times correspondents.

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Introduction

In the June 4, 2025 episode of The Daily, host Natalie Kitroeff delves into Operation Spider’s Web, a groundbreaking Ukrainian military operation that leveraged inexpensive drones to inflict significant damage on Russian warplanes. This operation marks a pivotal moment in modern warfare, showcasing Ukraine's ingenuity in countering superior military forces.

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The Genesis of Operation Spider’s Web

Background and Context

Mark Santora, one of the correspondents embedded with the Ukrainian military, provides an insider's perspective on the operation's inception. He describes how Ukraine has been grappling with continuous long-range missile bombardments from Russian bombers and naval assets:

“The Ukrainians do what they've done throughout this war. They have to adapt, they have to innovate, they have to find a low-cost solution.”
[03:33]

Identifying the Problem

The relentless missile attacks from Russian territory posed a significant threat to Ukrainian civilians and infrastructure. With traditional defenses stretched thin, Ukraine sought a novel approach to mitigate these assaults.

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Planning and Execution of Operation Spider’s Web

Conceiving the Strategy

Ukraine's response was to harness the power of drones, reflecting their consistent reliance on this technology throughout the conflict. Santora emphasizes the critical role drones have played:

“It's kind of hard to imagine how Ukraine would have survived without drones.”
[05:08]

Secrecy and Coordination

Operation Spider’s Web was meticulously planned in secrecy, even from American allies. President Zelensky personally oversaw the mission, highlighting its strategic importance:

“This operation was so high profile that President Zelensky himself oversaw it.”
[09:54]

Technical Deployment

The operation involved sophisticated tradecraft to conceal and deploy drones within Russian territory:

• Hiding Drones: Utilizing shipping containers as disguise, multiple layers ensured drones could be launched seamlessly.
• Training Drones: Advanced machine learning algorithms were employed to target the most vulnerable parts of Russian bombers, specifically fuel depots.

“They start with shipping containers... the roof containing the drones pops off, and the drones start to take to the air.”
[10:49]

Execution of the Attack

On Sunday, the operation was initiated precisely at 1:06 PM. The drones launched from concealed containers, attacking multiple airfields across Russia. Real-time footage captured dramatic scenes of explosions and burning aircraft:

“We start to see explosions, clouds of smoke rising up from airfields... it's just wildly dramatic images.”
[14:30]

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Impact and Consequences

Immediate Damage

The operation resulted in substantial damage to Russian military assets:

• Ukrainian Claims: Over 41 bombers and planes damaged.
• Western Estimates: Approximately $3.5 billion in damage.

“If the Ukrainian account is correct, $7 billion in damage done by drones that cost a few thousand dollars apiece.”
[16:24]

Strategic Significance

This attack not only inflicted material loss but also symbolized a shift in modern warfare dynamics. It underscored the effectiveness of low-cost technology in asymmetrical warfare.

“This attack should drive home how it can both affect what militaries think about in terms of their force protection.”
[16:39]

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Future Implications

Evolution of Drone Warfare

Operation Spider’s Web exemplifies the evolving role of drones in military strategies, prompting global militaries to rethink their defense doctrines and investments.

“The amount of adaptation and evolution that we've seen over the course of three and a half years has forced everyone who's paying attention to rethink some of those doctrines.”
[17:07]

Diplomatic Ramifications

The operation occurred shortly after President Trump’s meeting with Zelensky, where Ukraine was perceived as diplomatically weak. This bold strike signals a resurgence of Ukrainian resilience and strategic prowess.

“It's just a very secretive operation... Orchestrating this whole thing from inside of Russia.”
[10:48]

Potential for Escalation

While the operation showcases Ukrainian ingenuity, its long-term effectiveness in forcing Russia to negotiate remains uncertain. Santora highlights the complexities of achieving peace despite such military successes:

“Nobody wants peace more than Ukrainians... but none of us really know what will force Putin to stop this invasion.”
[20:22]

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Conclusion

Operation Spider’s Web represents a significant milestone in the ongoing conflict between Ukraine and Russia, demonstrating how innovation and strategic planning can level the playing field against a more formidable adversary. While its immediate impact is undeniable, the broader implications for future warfare and diplomatic negotiations continue to unfold.

“This is total war. And in total war, it's everything together that matters.”
[21:08]

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Notable Quotes:

• “It's kind of hard to imagine how Ukraine would have survived without drones.” — Mark Santora [05:08]
• “This operation was so high profile that President Zelensky himself oversaw it.” — Mark Santora [09:54]
• “We start to see explosions, clouds of smoke rising up from airfields... it's just wildly dramatic images.” — Mark Santora [14:30]
• “This attack should drive home how it can both affect what militaries think about in terms of their force protection.” — Mark Santora [16:39]

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This comprehensive summary encapsulates the critical elements of "Inside Operation Spider’s Web," providing listeners with an in-depth understanding of the operation's strategic significance, execution, and potential ramifications without needing to access the full podcast episode.

Transcript

[Dave DeFore]

Hey basketball Fans, I'm Dave DeFore, host of the Athletic NBA Daily, a basketball podcast from the Athletic and the New York Times. The NBA Finals are here. Join me Zena Keda, Esperaheny and the Athletics award winning basketball reporters as we dissect every dunk, buzzer beater and game changing play. New episodes drop six days a week, so trust me, we'll talk about everything that happened in every game. If you want an unfiltered take on the teams and players from people who live and breathe this sport, listen to the Athletic NBA Daily wherever you get podcasts.

[Natalie Kitroweff]

From the New York Times. I'm Natalie Kitroweff. This is the Daily Today, the story of Operation Spider's Web, an audacious sneak attack by Ukraine that caused billions of dollars in damage to Russian warplane with drones that cost as little as $600. My colleague Mark Santora explains why this strike is already being seen as a defining moment in the evolution of modern warfare. It's Wednesday, June four. Mark, we're coming to you because you are one of the correspondents who has been on the ground for the longest in Ukraine. You've been reporting from the front lines, embedding with the Ukrainian military. And we now know what happened this past Sunday was unlike anything we have seen so far in this war. You and a team of reporters have been working to uncover exactly what went down, how it went down, and I wanna get to those specific today. But first, can you just take us through the events as you experience them on Sunday?

[Mark Santora]

Sure. So, you know, you get used to a lot of reports of explosions every day here, whether it's here in Ukraine or something going on in Russia. But On Sunday around 1 o' clock, we started to get these really strange reports of explosions at airfields 3,000 miles from Ukraine. First we saw reports of explosions, explosions at an airfield all the way in Siberia. And as they started to come in, we started to get videos of how these attacks were being conducted. And it was really weird looking, right, because, you know, we're used to long range Ukrainian drone strikes going after, you know, Russian targets inside of Russia. But here, drones retired, we saw these trucks parked on the side of the road and then these small little quadcopters rising up from the trailer and taking off. And then, you know, cut images to burning planes and airfields. And so it quickly became apparent that in terms of how this strike was executed, in terms of its ambition, in terms of what it might mean for the war going forward, that this was something different. This was a signal event in this war.

[Natalie Kitroweff]

Okay, so a very big deal attack carried out in what seems to be a pretty sophisticated way. How did this happen, Mark? How did Ukraine pull this off?

[Mark Santora]

Well, this is Ukraine's answer to a problem that has bedeviled them throughout this war, which is how do you stop massive long range Russian missile bombardments? And these are launched from planes flying deep in Russian territory. They're missiles fired from ships and submarines out at sea, from land based systems far inside of Russia. So basically out of the reach of the Ukrainians. And these bombardments have become so routine in Ukraine that people can actually time when they want to go to the shelter by what's happening. For instance, a Russian bomber will take off from an air base deep in Russia and you'll get a warning saying that the bombers are at the starting line.

[Natalie Kitroweff]

A warning, like on your phone?

[Mark Santora]

Yeah, warning on your phone. It'll say, Russian bombers, Tu95 at the starting line. So that means you have about two hours till they get to the line launch point. You'll get an alarm, missiles have been launched. Then, you know, if you're in Kyiv, say, and depending on where the, the launch is from, you know, you have two, three hours for a cruise missile.

[Natalie Kitroweff]

Wow. It's like a countdown to an attack on your phone live.

[Mark Santora]

Yeah. So these bombers, everyone in Ukraine is intimately familiar with now the TU95. And it's kind of gone in waves in the war. The more US support they got with Patriot missiles and other things, the more secure people in some cities felt. As American support has faded, some of that feeling of security has faded with it because there's only a few really advanced weapon systems that can go after Russia's most advanced missiles. And Ukraine never had enough of them. But as America pulls back, they have even less.

[Natalie Kitroweff]

So it sounds like the Ukrainian government looks at this problem and says, okay, this is what we need to solve. How do we stop these long range missile attacks from these Russian bombers?

[Mark Santora]

100%. So the Ukrainians do what they've done throughout this war. They have to adapt, they have to innovate, they have to find a low cost solution. And so what they do is they turn to drones. Drones are the things that Ukraine has turned to time and again in this war to survive against an enemy that outnumbers them, that has a vastly bigger arsenal. I mean, honestly, it's kind of hard to imagine how Ukraine would have survived without drones. And you know, going to the front line over the last three years, you've just seen how they've transformed the Battlefield. I mean, every time now, if we go out to a frontline position with the Ukrainians, you have someone riding on the front seat with a shotgun, because really that's one of the only defenses against some of these kinds of smaller drones. So they're able to use these drones to hold defensive positions with fewer people than they might otherwise need.

[Natalie Kitroweff]

But Mark, how does this strategy, while successful on the front lines, get at that original problem we were talking about, which is striking Russia where it hurts, in Russian territory, hitting these bombers.

[Mark Santora]

So first of all, you know, all these guys on the front line, they're watching every day as Russian missiles and bombs are hitting the towns and cities where their families live. So they, just like everyone else, are, you know, desperate to find a way to do something about this. And so Ukraine begins another kind of drone program, which is to make long range drones. Not these small sort of little quadcopters, but drones that can fly hundreds of miles and carry powerful payloads of explosives. So Ukraine for the first time strikes a Russian airfield all the way back in December 2022. But Russia obviously starts to adapt to this new capability. Ukraine has. They've got robust air defenses, but also they start taking other measures. They build fortifications around fuel depots, at airports. They build decoys at the size of fighter jets to confuse the Ukrainians as to what's where. They put tires on the wings of planes in the hopes that if there is an explosion at the airport, the shrapnel doesn't. They do a number of steps that, you know, taken together, make it exceedingly hard for the Ukrainians to strike a blow that will do more than glancing damage.

[Natalie Kitroweff]

So again, the solution isn't there yet.

[Mark Santora]

Right? So about a year and a half ago, the Ukrainians decided they need to try something different. And they come up with this very secret plan. So secret, the Ukrainians say they didn't even tell the Americans. They try and find a way to bring these small drones, the ones that have been so effective on the front, into Russia close to these air bases where these bombers are based in the hopes that they can use them to catch the Russians by surprise and maybe at least slow the Russian bombardments down and give them more of a fighting chance. And they call this operation Spider's Web.

[Natalie Kitroweff]

We'll be right back.

[Sydney Harper]

Hi, this is Sydney Harper and I help make the daily one night, it's 10pm My colleagues working on the next day's episode are looking for a speech, this piece of tape that they really need to make the episode sing. They've tracked it down to a university library, and that library happens to be close to my house. So I hop into a car, I head across town. I get to the library. They're about to close. I'm copying the tape, uploading it to my computer, sending it off to my colleagues working on the episode. It makes it into the show the next day. It really helps make it shine. The whole effort is a success. And I'm telling you this because I don't think people realize that that level of teamwork and dedication goes into every episode that you hear on the Daily. That sort of collaboration takes people, it takes resources, it takes support from subscribers. So that's why I'm asking you to subscribe to the New York Times so we can keep bringing you the Daily Every.

[Natalie Kitroweff]

Okay, Mark, take us inside this operation. Operation Spider's Web.

[Mark Santora]

So there's a lot we don't know, and we're still working to piece it together. But what we do know is that this operation was so high profile that President Zelensky himself oversaw it. We know it was so secretive, they didn't even tell the Americans. And we know the goal was to secret these drones into. Into Russia and close to these air bases so they can hit these bombers. So Ukraine has to do two things for this operation to be pulled off successfully. They have to hide the drones and they have to train the drones. And let's start with the hiding. They start with thinking to themselves, what is the most common, ubiquitous thing you see on the roads? And it's shipping containers. These nondescript, hulking metal boxes that you see going up and down highways every day. And you don't give a second thought. They make a decision that they're going to turn those containers. Containers into a much more sophisticated weapons delivery system.

[Natalie Kitroweff]

And what does that look like?

[Mark Santora]

Well, think of a Russian nesting doll, right where you have the big doll inside the big dolls, a smaller doll and a smaller doll. So you have this container with a roof that can be popped off by remote control. But then inside of that container, we have another container. And that container holds the drones, and beneath the drones, chargers for those drones. And the roof of that smaller container can also pop off, at which point the drones can take off into the sky and launch their attack the minute they get the signal to go. And what makes it even crazier, and we're not 100% sure where each piece of this puzzle was assembled, but President Zelensky said they set up their main sort of headquarters to pull off this operation right across the street from the fsb, which is, you know, the Russian internal security services. So they're orchestrating this whole thing from inside of Russia at a secret base that's, you know, with a stone's throw from the Russian secret police, according to the Ukrainians. So you have people involved in every step of the way. You have the agents who snuck into Russia to help pull this off. You had the pilots who were going to fly these drones from a very far, remote location back in Ukraine. Each step along the way, you have spies and soldiers and drone pilots involved in executing this.

[Natalie Kitroweff]

Okay, so you said step two was training the drones. What did that look like?

[Mark Santora]

So their primary target is going to be these bombers. And so they want to teach the software how to hit these bombers to do the most damage that they can. And they happen to have some of these Soviet era bombers in a museum in central Ukraine, you know, back from the day when Ukraine was a part of the Soviet Union, long ago mothballed, but turned out to be quite useful in this mission. So what they do is they take some of the most sophisticated new machine learning, artificial intelligence algorithms that they've been testing and expanding throughout the war, and they train these drones to basically go after the most vulnerable spot on these bombers, which is where the fuel is kept, basically.

[Natalie Kitroweff]

Just clearly an enormous amount of tradecraft went into this.

[Mark Santora]

Yeah, I mean, I think obviously one of the big questions the Kremlin is wrestling with is how in the world could Ukraine have penetrated so deeply for so long to pull this off? And I think that's a, you know, we don't know the answer to that.

[Natalie Kitroweff]

Okay, so once they have these drones trained up, they have them hidden, they're in the country. What's the next step?

[Mark Santora]

It's time to attack. On Sunday, around 1:06pm, they get the order, the roof of these containers pops up, the roof containing the drones pops off, and the drones start to take to the air. And then we start to see explosions, clouds of smoke rising up from airfields. And at the same time, drones rising from containers are going and attacking airfields across Russia. And then we start to get from our intelligence sources direct video views from these drones on their attack mission. There's one really compelling one where you see from the drone's vantage point, the same thing the drone pilot would see it flying over an airfield as two, three bombers are on fire and it dives in to hit another one. And so you start to see these just wildly dramatic images coming out and the attack is underway.

[Natalie Kitroweff]

Yeah, I've seen these videos We've published them. It really starts to look at this point like a movie, like some sort of scene from Mission Impossible or something. I mean, this moment is just remarkable to watch in real time.

[Mark Santora]

Yeah, you know, it's really one of the kind of incredible things about this war that I don't even think we've fully understood, which is just how much of it has unfolded before the cameras. But, you know, video videos, they can lie or not tell the whole story. So our colleagues on Visual Investigations basically set to work right away to try and piece together both the videos coming from Ukrainian intelligence, but also Russian civilians, as well as satellite images which are still coming out to try and understand, okay, they were able to orchestrate this attack, but what effect did it have? And where we are Now, I think, 48 hours after the attack unfolded, is we can say with confidence that more than a dozen Russian bombers and planes suffered damage quite extensive in many cases. The Ukrainians say that the number could be as high as 41. And that amounts to, if the Ukrainian account is correct, $7 billion in damage done by drones that cost a few thousand dollars apiece. Even if it's half as much as Ukraine said and it's closer to the Western estimates, that's still $3.5 billion in damage. And you have to recall that this is Russia's strategic nuclear bombing fleet. So we' talking about how Russia has been using these to launch conventional weapons at Ukraine. Cruise missiles. This is also a key element of its strategic nuclear deterrence. And Russia is not thought to have more than 100 of these, you know, totally. And they're not making any more right now. So the loss of 10 or 20 would itself be really significant. If it's as high as the Ukrainian number, that's a third of that fleet. So we'll see what that tally comes to. But, you know, undoubtedly the attack put a big dent in the fleet.

[Natalie Kitroweff]

It's just remarkable to imagine these tiny, cheap little drones having that kind of an impact. But, Mark, as you've said, we've seen drones being used in this conflict for a long time now. What's different about this time?

[Mark Santora]

Yeah. So, I mean, aside from just the boldness of this attack, it is sort of an evolution in a revolution and the revolution of drones. For anyone who hasn't been paying attention, I think this attack should drive that home. How it can both affect what militaries think about in terms of their force protection, what they choose to invest in. It's kind of like, if you're to think about other Moments in wars where a new weapon comes to life. The weapon might have existed a bit, but then it's just used to great effect. So In World War II, for instance, you had the Germans using the V1 and V2 rockets to bombard London. You know, it would be some time, but that augered in the era of the missile. And we've seen how missiles transformed, you know, how countries fight or think about fighting or plan. Plan for fighting. And I think when it comes to drones, they've been around a while. They've. Obviously, what's happened here in Ukraine is it's gotten supercharged. And just the amount of adaptation and evolution that we've seen over the course of three and a half years has forced everyone who's paying attention to rethink some of those doctrines that were long held about what does it take to, you know, both win on the battlefield and also, you know, to prepare for the next fight.

[Natalie Kitroweff]

I also feel like there's another reason this attack is really important, and that's just the timing of it. It comes just a few months after Trump sat with Zelensky in the Oval Office and said Ukraine was not in a good position in its negotiations with Russia over peace, that it didn't have any cards. And now Zelensky and Ukraine have orchestrated this pretty advanced attack after a long stretch where Russia was dominating the battlefield. Like, he's saying Zelensky saying, no, wait, we actually do have some cards. Here they are. And so I'm wondering, Mark, how this affects the ongoing talks between Russia and Ukraine.

[Mark Santora]

So, first of all, you know, we talked about how this was a year and a half in the planning. So while President Zelensky was in the Oval Office being berated, he knew that this plot was, you know, being cooked up. So in any case, he knew he had some cards in his back pocket.

[Natalie Kitroweff]

Right.

[Mark Santora]

I think, you know, we talked a lot about what was Ukraine's goal with this operation. And obviously, a central goal was to slow down these bombardments. But there was a secondary goal which was to raise the cost of this war for the Kremlin. The Ukrainian theory of how do you stop this war? Is you have to force the Russians to stop. Diplomacy has so far failed. So the only way Ukraine sees this war ending is if there is enough pressure and cost on the Kremlin to end their war. So this attack was a part of that. And then we saw today another remarkable covert operation, which was the third attack on the bridge that crosses from Crimea into Russia. Now, again, this one just happened. Literally, you know, this afternoon, we don't know the damage, we don't know how successful it was. But it shows you what Ukraine's strategy here is, which is they're never going to have more people than Russia. Russia is willing to lose tens of thousands of soldiers every month. Ukraine has been most successful when they've, you know, used their ability to sort of act quickly. And whether it's surprise, deception, adaptation, that's where they've had the greatest success in this war. And so this operation, going after these Russian bombers, going after the Crimean bridge, again, these play to Ukraine's strengths.

[Natalie Kitroweff]

At the same time, Putin obviously has been really resistant to pressure this whole time. And I have to wonder whether, even with the latest successes, this has any chance of working, of forcing him to the table in a really earnest way.

[Mark Santora]

I have no idea. All I know for sure is that nobody wants peace more than Ukrainians. They want this war to be over. But none of us really know what will force Putin to stop this invasion and really either engage in good faith negotiations or agree to the immediate ceasefire that everyone, quite Frankly, Ukraine, the U.S. the Europeans all want. And what we have instead, since this diplomatic push has sort of kicked into high gear after Trump took office, is no closer to peace, but more violent week after week.

[Natalie Kitroweff]

In other words, Operation Spider's Web might end up having more of an effect on how we think about and conduct warfare in general than it will have on this actual war.

[Mark Santora]

Yeah, I mean, you know, obviously everyone is always looking for that thing that will be the moment that turns the war or that leads to the end of the war. But the honest truth is, you know, this is total war. And in total war, it's everything together that matters. So this operation will help people if it even, you know, lessens the bombardments to some degree. That's thousands of people in a city or town who might not have to face a missile bombardment that otherwise would have come their way. But, yeah, at the end of the day, I think the Ukrainians are under no illusions. This is their only strategy, which is to fight back, to increase the cost on the Kremlin and just hope at some point between their own actions, their own fight and then Western support, that that pressure becomes enough. Where Russia decides. Okay, enough.

[Natalie Kitroweff]

Mark, thanks for being here and stay safe.

[Mark Santora]

Thank.

[Natalie Kitroweff]

You. We'll be right back. Here's what else you need to know today. On Tuesday morning, Israeli soldiers opened fire near crowds of Palestinians who were walking toward a food distribution site in southern Gaza. The Red cross said that 27 people were killed. In the attack, the Israeli military said it had fired near a few people who had strayed from the designated route to the site and who didn't respond to warning shots, saying they had, quote, posed a threat to soldiers. A senior administrator at a hospital a few miles from where the shootings took place said that many of the victims were children aged 10 to 13. And the Trump administration is proposing a deal to allow Iran to continue enriching uranium at low levels while the US and other countries work out a plan to eventually block Iran's path to a nuclear weapon in exchange for giving it access to fuel for nuclear power plants. The proposal is seen as a bridge, for now between the current situation of Iran rapidly producing near bomb grade uranium and the American goal of Iran enriching no uranium at all. This was the first indication since Trump took off office that the US And Iran might be able to find a compromise over Tehran's ambitions to build a nuclear weapon. Officials in Tehran indicated that a response would come in several days. And finally, on Tuesday afternoon, Elon Musk lashed out against the ambitious Republican bill that's intended to enact Trump's domestic policy agenda and that's been backed by the president. Musk posted on X that the measure, which the White House has called the Big Beautiful Bill is, quote, a disgusting abomination, saying it was, quote, massive, outrageous, pork filled, and would, quote, massively increase the already gigantic budget deficit. Musk also hinted that he might support efforts to unseat lawmakers who backed the bill in the 2020 midterm elections, saying, quote, in November next year, we fire all politicians who betrayed the American people. While Musk directed his ire at Congress, the comments amounted to his biggest public break with Trump since the two joined forces during the campaign. Today's episode was produced by Olivia Natt, Caitlin o' Keefe and Anna Foley. It was edited by Dan Devin Taylor and Chris Haxel, with help from Mike Benoit. Contains original Music by Pat McCusker, Rowan Niemisto and Elisheba Itube and was engineered by Alyssa Moxley. Our theme music is by Jim Brunberg and Ben Landsberg of Wonderly. That's it for the dance. I'm Natalie Kitroweth. See you tomorrow.