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Jun 5, 2025  |  
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NextImg:Max Boot's Pearl Harbor Analogy Reveals What He Really Wants

Over the weekend, Ukraine launched a daring operation deep inside Russia. The Ukrainians managed to smuggle almost 120 drones into Russia itself and deployed them against multiple airfields across the country, with one as far afield as Siberia — roughly 3,000 miles away from the frontline. Dubbed Operation Spider’s Web, the attacks targeted Russia’s fleet of long-range strategic bombers that have been used against Ukrainian cities throughout the war.

Though the exact extent of the damage is in dispute, experts consulted by the New York Times said that the strikes were a “symbolic blow” to Russia’s bombing campaign. While Ukrainian troops have crossed the border with Russia before and even held a foothold for a significant period of time, this weekend’s incursion is by far the deepest and most damaging one Ukraine has mounted since the war began in 2022.

As with every escalation of this war that has resulted in hundreds of thousands of deaths, the neocons are absolutely giddy. In fact, professional warmonger and Lex Luthor cosplayer Max Boot lauded the attacks, and what they implied for the conflict going forward, as a “brilliant and daring gambit” in his late Sunday op-ed for The Washington Post titled, “Ukraine just rewrote the rules of war.”

To Boot, this new Ukrainian operation belongs in the annals of military history as an audacious and groundbreaking display of ingenuity and grit, like the Japanese attack on Pearl Harbor on December 7, 1941.

Yes, you read that correctly. Max Boot compared it positively to the Japanese attack on Pearl Harbor.

“On Sunday morning, Dec. 7, 1941, the Imperial Japanese Navy rewrote the rules of warfare. Almost no one had imagined that the Japanese could sneak across an entire ocean to attack an ‘impregnable fortress,’ as U.S. strategists had described Hawaii. Yet that is just what they did,” he opens the op-ed.

“Japanese aircraft launched from six aircraft carriers managed to destroy or damage 328 U.S. aircraft and 19 U.S. Navy ships, including eight battleships. The Pearl Harbor attack signaled the ascendance of aircraft carriers as the dominant force in naval warfare. The Ukrainians rewrote the rules of warfare again on Sunday.”

Boot is correct that his analogy is somewhat inapt because the attack on Pearl Harbor was a preemptive strike, while the attacks this weekend have come years into a long war. And he’s right that Pearl Harbor, along with the sinking of the German battleship Bismarck by British torpedo planes in May 1941, heralded the ascendance of aircraft carriers as the centerpiece of naval warfare, replacing heavily armed and armored capital ships.

But there are other parallels between the Ukraine-Russia conflict and the Pacific War that he overlooks, and none of them go the way Max Boot would like.

“The drone strike, while raising the strategic stakes and no doubt provoking Russian retaliation, is exactly the kind of high-pressure tactic needed to persuade Putin to negotiate in earnest,” Boot concludes.

Replace drone with Pearl Harbor, Russian with American, and Putin with Franklin Roosevelt, and you’ve got the exact rationale the Japanese high command used to justify the attack on Pearl Harbor.

The basic Japanese strategy at the beginning of World War II was to disable the U.S. Pacific Fleet in one decisive blow, quickly seize resource-rich Western colonies in Southeast Asia (namely British Malaya, the Dutch East Indies, and the Philippines), and then fortify their new conquests to such a degree that attempting to retake them would wear down the Western powers’ resolve and bring them to the negotiating table.

But as everyone should remember, the Hawaiian gambit didn’t work out too well for its perpetrators. Less than four years later, the Japanese Empire had crumbled, its economy lay in shambles, and two nuclear weapons had devastated Hiroshima and Nagasaki (it should be noted that Russia currently has the largest stockpile of nuclear weapons).

The Japanese failed to completely knock out America’s naval capabilities, largely due to the fact that the U.S. aircraft carriers stationed at Pearl Harbor were not in port during the attack. American industrial might was quickly able to replace the losses suffered during the Dec. 7 attack.

Ukraine claims that it hit 41 Russian aircraft during its attack, while at least one Russian source said only 13 planes were damaged, according to the NYT. Western experts estimated that around 20 Russian “strategic aircraft” were destroyed or damaged, including 10 long-range strategic bombers. Before the attack, Russia had an estimated 80 strategic bombers, so depending on whether all the planes hit during Ukraine’s attack were strategic bombers or other types of planes, Russia may have lost between 12 percent and half of its bomber fleet. That’s not insignificant, but in the grand scheme of the ongoing war, it’s not the knockout blow that Ukraine needed to bring Russia to its knees.

Boot hand waves this fact, writing, “Operation Spiderweb will not be a decisive blow against the Russian military any more than the Pearl Harbor attack was a decisive blow against the U.S. military. But just as Pearl Harbor signaled that Japan would be a far more formidable foe than most Westerners had expected, Sunday’s attack shows, yet again, that the Ukrainians are proving far more resilient and adaptable fighters than anyone had anticipated before the start of Russia’s full-scale invasion more than three years ago.”

But if that kind of maneuver doesn’t achieve some kind of overarching strategic advantage for the side that executes it, it usually just ends up kicking the hornet’s nest, as Imperial Japan can attest. The Japanese in battle after battle in the Pacific showed their (oftentimes literal) suicidal courage and dedication to their cause, but it ended with the Japanese signing the instrument of surrender on the deck of the USS Missouri in Tokyo Bay, all the same.

Rather than tip the scales in favor of the Ukrainians at the ongoing peace negotiations in Turkey, the recent attack appears to have had the opposite effect on the Russians. In response, Russian media reportedly described the operation as a “terrorist attack,” and the Russian envoys unveiled a new memorandum on proposed peace terms. Under their plan, Russia would officially gain Crimea and the eastern regions of Ukraine that have seen the bulk of the frontline fighting during the war, NBC News reported. Additionally, Ukraine would have to reduce the size of its army and adopt a “neutral” stance between Russia and the Western powers.

The Russo-Ukraine war has developed into a war of attrition since the failure of Russia’s dash for the Ukrainian capital in early 2022, resembling the trench warfare of World War I more than the blitzkrieg the country experienced during World War II. The Japanese had a similar strategy to wear down Allied resolve by defending heavily fortified islands to the last man. But in wars of attrition, the side with the larger economy almost always wins out in the end. Russia’s GDP is about 10 times larger than Ukraine’s, and it’s been patently clear for years now that Ukraine is kept afloat only by the mountain of foreign aid provided by the West.

Boot and his neocon pals seem to have the same opinion of Russia as Hitler did right before the German invasion of the Soviet Union in mid-1941: “We have only to kick in the door and the whole rotten structure will come crashing down.”

But underestimating Russian resolve often proves a catastrophic mistake. It didn’t work out for Napoleon, and it didn’t work out for Hitler. Russia has proven time and again its willingness to endure massive casualties and embarrassing setbacks to achieve its goals.

The development and utilization of new drone technology may give Ukraine a tactical edge in the short term, as Boot argues, but no amount of wonder weapons can change the fundamentals of war: industrial capacity and manpower. The Germans made incredible strides in military technology during World War II, including the first jet aircraft, but it wasn’t enough to turn the tide.

Boot might be somewhat correct that Ukraine has utilized an innovative technology, drones, in a clever way, but the larger strategic move hasn’t “rewritten the rules of war” at all. It’s an operation utilized by desperate nations that often feel they have no other way to gain an advantage, and it rarely works out. Boot and his ilk laud it not because they actually believe that it will give Ukraine an advantage in negotiations, but because they crave the inevitable escalation. Never mind that this inches Russia closer to a nuclear response. The raw destruction is all that matters to these people, especially when it’s directed toward a particularly hated bogeyman.