What the US can learn from Ukraine's remarkable Operation Spider Web

The Hill

09-06-2025

Operation Spider Web, the brilliantly audacious Ukrainian drone attack on several Russian airbases located thousands of miles from the battlefield, has been largely lauded as a major tactical and strategic success. Many supposed lessons are being drawn — some, no doubt, applicable, but others hastily jumped to and unwarranted.
The spycraft involved in this attack was extraordinary — hiding drones in the tops of boxes loaded on Russian trucks whose drivers were unaware of their cargo and then released on signal ranks with the greatest of exploits.
While Pearl Harbor is an inappropriate comparison, as Ukraine has been at war for over three years, Jimmy Doolittle's daring B-25 raid over Tokyo in April 1942 is a good parallel. After all, who would have thought B-25 bombers could fly off a carrier deck?
Perhaps the best analogy is Britain's Special Air Service, created in 1941 by then-Major David Stirling to conduct hit and run raids on Nazi bases in the North African campaign. Mounted in jeeps, the Special Air Service crisscrossed the desert delivering not just one but multiple surprise attacks on German airbases, physically destroying with bullets, hand grenades and explosive charges more enemy aircraft than the Royal Air Force would ultimately shoot down.
To begin, the lesson learned was that the process must distinguish between what may be valid or not in the attacks against five Russian airbases: Olenya, Belaya, Dyagilevo, Ivanovo Severny and an attempted strike on Ukrainka.
The real damage was reportedly done at Olenya, where eight Tupolev TU-95-MS bombers loaded with KH-101 stealth air-launched cruise missiles were destroyed.
This struck at the heart of the Russian strategic air force. Given the low operational readiness rates due to maintenance issues, this may have crippled about 70 percent of the force, even though only about one third of the aircraft were physically destroyed.
While the other raids reportedly accounted for seven TU-22M3 bombers, two A-50 Airborne Warning and Control System aircraft and one An-12 transport aircraft, the operational impact was not nearly as great.
But no matter: Spider Web was an instant victory. However, the larger consequences are yet to take hold.
In a phone call with Donald Trump, Vladimir Putin vowed revenge. The question is, short of nuclear weapons, what more damage can he inflict on Ukrainian cities than he is doing now?
In 1940, to save the Royal Air Force that was being eviscerated on the ground and in the air by superior Nazi numbers, Winston Churchill ordered the bombing of Berlin. Enraged, Hitler ordered the bombing of British cities and a 'Blitz' that would continue with V-1 and V-2 rockets until the war's end in 1945, thus saving the Royal Air Force's air bases and enabling the winning of the Battle of Britain.
It is not clear what Putin will do. There is talk in Ukraine of a major Russian summer offensive. If true, that offensive could fizzle as the others have. Or it could succeed.
Success could be Putin's means of retaliation and vengeance for Operation Spider Web. While it is unlikely Russia's summer offensive will lead to the destruction or neutralization of the Ukrainian military, it could achieve one major breakthrough: surrounding and blockading Odesa.
Closing the port and, in essence, sealing off Ukraine from the Black Sea, would have major implications, and not only for Kyiv, which is dependent on the trade and export of its grain. Importers of grain would also be hit hard.
That might give Putin added leverage because outside states could impose pressure on Kyiv to negotiate and thus lift its blockade. Since Ukraine has no navy and Russia's is hiding out of range, it would be drones and missiles designed to attack the bridges of cargo ships that would be the deus ex machina, along with sea mines to close the port. This would be followed by or preceded with massive attacks on Odesa and its port.
One knee-jerk reaction is to sound the alarm over U.S. military bases' vulnerability to this form of attack.
But didn't 9/11 teach us anything? Surprise works. And attacking U.S. bases from within would be a given in time of war. In fact, we have seen shootings and other acts of violence taking place on many bases.
But let's not panic. Common sense prevails. Let's not isolate the military even more because of this alleged vulnerability and the Ukrainian raid.
What should be taken from Operation Spider Web is how we might shock and awe our potential adversaries through innovative actions. That is the place to focus. But will we?
Harlan Ullman, Ph.D., is UPI's Arnaud deBorchgrave Distinguished Columnist, a senior advisor at Washington, D.C.'s Atlantic Council, the chairman of two private companies and the principal author of the doctrine of shock and awe. He and David Richards are authors of a forthcoming book on preventing strategic catastrophe.