Ukraine’s Strikes, Like the Doolittle Raid on Tokyo in World War II, Show Putin That He’s Not Master of This War
The press is describing the drone offensive as ‘Russia’s Pearl Harbor,’ but the Doolittle raids are a more apt analogy.

Ukraine is launching daring attacks against Russia, drawing comparisons to Japan’s raid on Pearl Harbor. A closer precedent, though, would be America’s Doolittle Raid on Tokyo — cause for celebrations in the attacked country that destroy the aggressor’s narrative that victory is near.
“Never, never, never,” Winston Churchill wrote in “My Early Life,” his 1930 memoir, “believe any war will be smooth or easy — or that anyone who embarks on the strange voyage can measure the tides and hurricanes he will encounter.”
On Tuesday, Ukraine, using underwater explosives, damaged the Kerch Strait Bridge connecting Russia to the occupied Crimea Peninsula, halting traffic. The bridge is a project of President Putin, aimed at cementing his territorial claim. Hitting it boosted Ukraine’s morale while sapping Russia’s.
The Kerch operation followed Sunday’s drone attack that may have destroyed a third of Moscow’s nuclear bombers on the ground. Mr. Putin is learning Churchill’s “lesson” that “the statesman who yields to war fever must realize that once the signal is given, he is no longer the master of policy but the slave of unforeseeable and uncontrollable events.”
The press described Ukraine’s drone offensive as “Russia’s Pearl Harbor.” Both strikes were daring, innovative, and crippled a key component of their foe’s military. Yet Ukraine’s attacks were carried out during open warfare, making getting caught off guard far more humiliating for Russia.
America was “at peace” with Japan before Pearl Harbor, President Franklin Roosevelt reminded Congress on December 8, 1941. “At the solicitation of Japan,” he said, America “was still in conversation” with that country “looking toward the maintenance of peace in the Pacific.”
The architect of the Pearl Harbor attack, Admiral Isoroku Yamamoto, was depressed following the “date that will live in infamy.” He felt that failing to declare war made Tokyo’s goal — forcing bigger, stronger America to back down — impossible.
“I fear,” Yamamoto has been quoted as saying, “all we have done is to awaken a sleeping giant and fill him with a terrible resolve.” There’s no evidence of the admiral using that phrasing, but it reflects his fears of what came to pass.
Russia launched its largest bombardment of Ukrainian cities last week, showing that Mr. Putin is no more inclined to peace than Imperial Japan. His resolve isn’t showing signs of weakening — though in a totalitarian state, dissent is hidden — but he’s been dealt body blows by an opponent he mistook for an easy mark.
Tokyo couldn’t have known that the ultimate price for its attack would be two atomic bombs. Because Russia maintains the world’s largest nuclear arsenal, though, President Trump has warned both invader and invaded that they are risking World War III.
Mr. Trump posted on Truth Social last week that Mr. Putin “has gone absolutely crazy” after his attack on civilians in Ukrainian cities. Last Tuesday, the American president said the would-be tsar is “playing with fire” and “doesn’t realize that if it weren’t for me, lots of really bad things would have already happened to Russia.”
Although the drone operation echoed Mr. Trump’s remarks, the White House said it had no foreknowledge of the attacks. That would mirror Japan’s decision not to notify its Axis allies at Berlin that it planned to hit America’s Pacific Fleet. The move left Nazi Germany no choice but to declare war on America, too, sealing Germany’s own fate.
Following Pearl Harbor, Washington — like Ukraine after Russia bombed its cities — knew it had to counterpunch. This task fell to Lieutenant Colonel James Doolittle, who launched 16 bombers from United States Ship Hornet to hit Tokyo and other Japanese cities on April 18, 1942.
Doolittle’s raid shook Japan’s sense that its home islands were invulnerable, but the raiders couldn’t carry enough fuel to return to Hornet. They landed in occupied Chinese territory, where Japanese forces executed 250,000 civilians in retaliation for helping some of the American flyboys escape. Eight American crewmembers were captured by the Japanese.
Ukraine cannot foresee how this war ends any more than Japan in 1941, but its defiance has proven the wisdom that Churchill imparted 100 years ago. “Always remember,” he wrote, “however sure you are that you could easily win, that there would not be a war if the other man did not think he also had a chance.”