Drones Don’t Wear Boots: The Battlefield Education of Vladimir Putin

By Derek H. Burney

May 16, 2026

Things are not going well for Vladimir Putin, either on the battlefield with Ukraine or on the home front.

The Russian dictator is displaying many of the classic signs of fin-de-regime decay, paranoia, and instability as Ukraine’s use of drone warfare makes a myth of the Russian territorial advantage long symbolized by the ravaged boots of Napoleon’s troops.

Drones don’t eat, they don’t march, they don’t die of exhaustion, and they don’t wear boots.

This year’s version of the May 9th Victory Day Parade in Moscow commemorating the Soviet Union’s success against Nazi Germany was a pale shadow of former celebrations.

Absent were the customary heavy tanks, ICBMs and armoured military vehicles. This parade rolled through Red Square after the war on Ukraine ran longer than the Soviet Union’s World War II battle.

Persistent Ukrainian drone strikes deeper into Russia targeting both military facilities and energy producers prompted Putin to request a brief ceasefire. He did not want Ukrainian drones or missiles raining on his parade.

Then on May 13th-14th, Putin launched his own drone attack — more than 14,000 strikes in 24 hours — as if he were exorcising his grudge against drones by projecting it onto Kyivans, 24 of whom were killed, dozens more of whom were injured.

At this writing, Ukraine has retaliated overnight May 16th-17th with 600 drone strikes against 14 regions in Russia, including Moscow.

More than four years into Putin’s war, his progress has been significantly hamstrung by superior Ukrainian drone and missile technology. In what CBC’s Murray Brewster reported as a “stunning reversal” in the training dynamic, Canadian and Latvian troops are now in training exercises with Ukrainian drone operators on unmanned ground vehicles.

Russian casualties are estimated to be well over one million, more than twice the Ukraine count.

There is a stark gap in motivation and morale: Ukrainians are fighting to defend their homeland; most Russian soldiers have no idea why they are fighting other than for the money.

In April, for the first time since 2024, Ukraine regained more land than it lost. The Russian-tilted peace process being promoted by President Donald Trump is proving to be a chimera.

When Putin suggested that the war was soon coming to an end – at least partially to assuage growing discontent in Russia – he suggested former German Chancellor Gerhard Schröder as a potential mediator between Russia and Europe.

Given Schröder’s long-time involvement as a lobbyist for the Nord Stream pipeline and other Russian energy projects, this idea was swiftly rejected by EU’s top diplomat, Kaja Kallas.

Ukrainian drone and missile strikes targeting Russian oil export facilities, refineries and military plants have increased in recent months. In late April, Ukraine intensified attacks on the Russian energy hub of Perm, more than 1,400 kilometres deep into central Russia.

According to the Institute for the Study of War (ISW), a series of subsequent strikes in early May burned roughly 70% of Perm’s Production Dispatch Station, a major pumping, storage and distribution hub for the transport of Siberian oil.

Seventy percent of Russia’s population, including those 1000 miles away from Ukraine who were once considered safe, are now within Ukraine’s reach. As Ukrainian forces become more effective, they underscore Putin’s weakness.

A series of Ukrainian attacks also recently demolished the refinery and the oil export Port of Tuapse on the Black Sea – a popular tourist resort area. Ukraine’s own Flamingo cruise missile was used on May 5 to hit a facility 900 miles away in the Russian city of Cheboksary that makes navigation systems for drones and missiles.

Seventy percent of Russia’s population, including those 1000 miles away from Ukraine who were once considered safe, are now within Ukraine’s reach. As Ukrainian forces become more effective, they underscore Putin’s weakness.

Russian forces have notably failed to capture the whole of the Donbas region of Eastern Ukraine which Putin frequently said was the sine qua non for any peace deal. Inflicting more pain on Russia the longer Putin holds out is what Ukraine believes is the most credible path to peace.

Indeed, on May 14th, the ISW stated that it “is no longer prepared to forecast when Russian forces might seize Donetsk, including the Fortress Belt, since the slowing rate of Russian advances and the challenging nature of the Ukrainian-held terrain in Donetsk makes it unclear that Russia is capable of seizing the territory at all.”

It added: “Russia’s exaggerated territorial ambitions and aggressive territorial demands run completely counter to battlefield reality.”

As quoted in Yaroslav Trofimov’s Wall Street Journal piece of May 6th, Putin’s Strongman Image is Fading as Ukraine Brings War Home to Russia, Victoria Bonya, an Instagram influencer and former Russian TV star who now lives in Monaco, stated on Instagram that Putin was “unaware of the country’s real problems because thieving governors and bureaucrats keep lying to him, and because the country is governed by fear.”

Putin uses oil exports to fund his war. Following its attack on Iran, the U.S. lifted previous sanctions on Russian oil. But Reuters reported in late March — before the most recent Ukrainian strikes — that “at least 40% of Russia’s oil export capacity has been disabled by Ukrainian drone strikes – the most severe oil supply disruption in the modern history of Russia.”

As Peter Dickinson pointed out in a recent Atlantic Council piece, Russia’s size is now a vulnerability. It does not have enough air-defence systems for the vast land expanse and they were clearly insufficient to provide cover for the traditional Victory Day Parade. Instead, most systems protect the Kremlin and Putin’s mansions. Putin is spending more time in underground bunkers these days and taking other security precautions due to worries about potential coup or assassination attempts.

European leaders have stressed that Russia must be defeated in Ukraine and Putin cast as a war criminal whom they believe could one day attack a NATO ally if he is allowed to win the war. The EU is scrambling to fill the financial void left by the U.S.

Some see Russia’s growing internal disquiet as the greatest challenge that Putin has ever faced. Despite increasing restrictions blocking most online activity, rumours abound about alleged coup plots and squabbles within parts of the security establishment, particularly those with responsibility for the war with Ukraine.

Keep in mind Churchill’s famous October 1939 description of Russia as “A riddle, wrapped in a mystery, inside an enigma.” He argued then that “Russian actions were hard to predict, the key to understanding them was Russian national interest.” That is most definitely still the case, complicated by the nuance in every autocracy that “national interest” is often mistaken for, then subjugated to, the personal needs of the autocrat.

John Sullivan, who was the U.S. Ambassador in Moscow when the invasion of Ukraine began in 2022, observed recently, “In Russia, they say things don’t happen fast, but when they do, they happen fast.” That may be the case with the precariousness of Putin’s leadership.

The power dynamics in Ukraine and Europe are shifting, and not in Putin’s favour. Trump’s vacillation on Ukraine is prompting Kyiv to act more resolutely and creatively in its own defence. His petulant tirades against NATO are stimulating more unity and resolve among European leaders to take greater charge of their security challenge.

Meanwhile, Trump has his hands full with domestic priorities, the evolving quagmire in Iran and his Summit with China’s president Xi. He has less and less time for his “friend” in Moscow.

Derek H. Burney is a former 30-year career diplomat who served as Canada’s Ambassador to the United States from 1989-1993. He now shares operations of a family cattle and horse ranch in Colorado.