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When Russian forces levelled Chechnya’s capital, they killed thousands, strengthened Putin’s early grip on power and introduced vicious tactics they’d later use in the Syrian war. Could Ukraine be next?

Russian soldiers rest in the rubble of Minutka square in Grozny, Chechnya's capital, in February of 2000 after an assault ordered by Russia's then-new President Vladimir Putin.Dmitry Belyakov/The Associated Press

With mounting fears of urban warfare as Russian forces advance toward the outskirts of Kyiv, analysts are beginning to draw lessons from President Vladimir Putin’s brutal tactics in his first siege of a European city: the Chechen capital of Grozny.

The battle of Grozny was a horrific four-month bombardment that nearly obliterated the city, killing thousands of people in indiscriminate shelling in the winter of 1999-2000. The Russian military fired massive barrages at the city, using long-range heavy artillery, tanks, multiple-rocket launchers, warplanes, cluster bombs and even ballistic missiles.

Grozny became the most destroyed city on Earth, according to a United Nations assessment. But despite the enormous death toll, the conquest of Grozny made Mr. Putin hugely popular. It brought him his first election victory and consolidated his grip on power.

Mr. Putin sits in a Su-27 fighter jet in March, 2000, after a flight over the Chechen war zone.ITAR-TASS/The Associated Press

Grozny also taught him a style of warfare that he used later in Syria and is now beginning to apply against another outnumbered and outgunned enemy, this time in Ukraine, analysts say. There are already signs of a Grozny-style siege in Ukrainian cities such as Kharkiv, where Russian shelling has destroyed dozens of buildings in recent days.

Last week, British Prime Minister Boris Johnson warned that Mr. Putin’s instinct will be “to double down and to try and ‘Grozny-fy’ Kyiv” if the Ukrainian resistance continues. It would reduce the Ukrainian capital to rubble, he said. “That would be an unalterable moral humanitarian catastrophe, and I hope he doesn’t do that.”

This week, the British Defence Ministry warned that Mr. Putin is doing exactly that. In an intelligence update, it said the Russian army – in its attacks on populated areas in the cities of Mariupol, Chernihiv and Kharkiv – was using similar tactics to its 1999 assault on Chechnya, using both air and ground-based munitions.

Kenneth Roth, executive director of Human Rights Watch, says the Russian siege of Grozny is “perhaps the closest analogy” to today’s war. “Already there are signs that Russian forces in Ukraine are moving in a similarly indiscriminate direction,” he wrote in a commentary last week, noting that Russian forces have used cluster bombs on civilian areas in Ukraine.

Frank Ledwidge, a senior lecturer in military capabilities and strategy at the University of Portsmouth in Britain, said Russian commanders could “default” to the approach that they used in Grozny. “This means bringing Kyiv under siege, blockading and starving the population, and shelling and bombing indiscriminately,” he said in a published commentary.

“If unchecked, we are looking at an operation of many months,” he said. “The idea is to break the will of the people to resist. There is no other possible purpose for the kind of weapons that are being brought up for deployment – notably the heavy artillery, thermobaric rocket launchers and attack helicopters.”

In a city of three million people, these weapons can have “no legitimate military purpose – unless one considers that terrorizing a civilian population into total submission is legitimate.”

Ukrainian evacuees in Irpin, on the northwestern outskirts of Kyiv, cross a bridge destroyed by Russian shelling on March 7. The Geneva conventions say that damage to infrastructure must be kept to a minimum and civilians have to be protected.DIMITAR DILKOFF/AFP via Getty Images

Mr. Putin was almost totally unknown to the Russian population when president Boris Yeltsin plucked him from an intelligence job to make him prime minister in August, 1999.

He had spent his career in the shadows, including 16 years as a KGB agent. To build his popularity in the few months before a scheduled election, he needed a high-profile victory – and Chechnya was the target that he chose.

At the time, Russia was at peace. Mr. Yeltsin’s earlier attempt to subdue the rebellious Chechen region in Russia’s southern borderlands had ended in a ceasefire and withdrawal in 1996.

But just a few weeks after Mr. Putin became prime minister, there was a mysterious wave of bombings of apartment towers in Moscow and southern Russia, killing hundreds of people in four explosions. Mr. Putin blamed the Chechens and used it as the central pillar of his campaign to rouse Russian support for a military offensive against the rebels.

Many analysts, however, later said there was circumstantial evidence that it was Mr. Putin’s own security agents who planted the apartment bombs.

When a resident spotted three men carrying large sacks into the basement of an apartment block in the city of Ryazan, police arrested the men and discovered they were Russian secret service agents. It would have been the fifth detonation of an apartment building. The Russian authorities swiftly claimed it was merely a “training exercise.”

At top, smoke rises from a destroyed Russian apartment building on Sept. 9, 1999.Ivan Sekretarev/The Associated Press

Outgoing president Boris Yeltsin, right, shakes hands with Mr. Putin on Dec. 31, 1999.WILLIAM WEST/AFP/Getty Images

Nine days after the Ryazan incident, Mr. Putin announced the launching of a Russian military invasion of Chechnya. At the time, Mr. Yeltsin was still president, but his health was declining, his power was eroding and he had decided to step down soon. In his memoirs later, he said the 1999 invasion of Chechnya was essentially Mr. Putin’s idea.

By mid-October, Russian armoured forces had captured a strategic ridge within artillery range of Grozny, and the siege of the city began.

The opposition was much smaller than it is today in Ukraine. There were only a few thousand Chechen rebels, armed mainly with light weapons. But they fought fiercely and refused to surrender. Unwilling to face them directly in battle, the Russian military resorted to massive firepower from a safe distance, using thousands of heavy artillery weapons, tanks, aerial bombs, ballistic missiles and multiple rocket launchers with thermobaric weapon warheads (also known as vacuum bombs).

In one of the most notorious attacks, the Russian military fired short-range Scud ballistic missiles into Grozny’s central marketplace, killing more than 140 people, including many women and children, and injuring hundreds more.

Mr. Putin ordered that all Chechen males between the ages of 10 and 60 must be arrested and interrogated on suspicion of “terrorism.” Thousands of Chechens disappeared into Russian custody and were never seen again.

By the time the Russians captured Grozny and ended the siege in February, 2000, the city was decimated. Block after block was smouldering rubble. Hundreds of buildings had been turned into a wasteland. The city, with a population of half a million before the war, was reduced to a ghost town. An estimated 25,000 civilians had been killed in Grozny and across Chechnya in four months. More than 200,000 civilians – a quarter of Chechnya’s population – had fled from their homes.

At top, a sign in Grozny says 'peace to Caucasus, peace to everybody!' in 1995, when Mr. Yeltsin was still in power; at bottom, a sign at the same block in 2019 features Mr. Putin and former Chechen president Akhmad Kadyrov.ALEXANDER NEMENOV/AFP/Getty Images

Grozny was often compared with Stalingrad, the Soviet city that was destroyed during months of fighting with Nazi invaders in the Second World War. But while the Soviets preserved some of the bombed ruins in Stalingrad as a war memorial, the Putin government has erased any evidence of its bombardment in Grozny. The city was rebuilt with garish neon-lit skyscrapers and shopping malls. Giant portraits of Mr. Putin were erected throughout. Streets were named after him and his generals.

Mr. Yeltsin, meanwhile, had resigned on Dec. 31, and an election was held in March, where Mr. Putin – boosted by his popular victory in Chechnya – won by a landslide margin of 24 percentage points over his nearest rival.

Since then, Mr. Putin has used the Grozny lessons again and again: choosing battles with weaker enemies and overwhelming them with Russia’s military firepower in places such as Georgia, Syria and eastern Ukraine.

After he ordered troops into Syria in 2015, Russian warplanes devastated cities such as Aleppo with deadly bombing attacks. Human-rights groups estimated that Russian bombs killed at least 1,700 Syrian civilians, often in hospitals, schools and residential buildings.

Ukraine has a much bigger population and greater weaponry than the Chechen rebels, and Mr. Putin might not have the same overwhelming edge in firepower that guaranteed his victory in Grozny. But the early bombardments of Ukrainian cities such as Kharkiv and Mariupol suggest that Mr. Putin is willing to use his Grozny experience yet again.

Geoffrey York was The Globe and Mail’s bureau chief in Moscow from 1994 to 2002 and spent weeks in Grozny during the two Chechen wars.

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