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Douglas Century is a Canadian-born, New York-based author and journalist, whose latest book is The Last Boss of Brighton: Boris “Biba” Nayfeld and the Rise of the Russian Mob in America.

When I began working on the Last Boss of Brighton, I didn’t plan to write a single word about Vladimir Putin. My book is about the rise and fall of a notorious Soviet-born mobster named Boris Nayfeld – aka ”Biba” – the last living boss of the old-school Russian mob in America.

But according to the book’s index, I’ve made around a dozen references to the Russian President. It’s not surprising, in hindsight: Mr. Putin and Russian organized crime have been inextricably linked almost from his emergence as a public figure in the early 1990s.

Forget the pop mythologizing about Al Capone and John Gotti, Pablo Escobar and Joaquin (Chapo) Guzman: In my view, Mr. Putin is the most brazen, powerful and wealthy mobster of all time.

Many Western analysts have attributed Mr. Putin’s Machiavellian nature to his early career as a KGB officer. That’s true – but only in part. It’s also the former street thug in Mr. Putin, coupled with his long-standing connections to prominent Russian organized crime figures, that makes him such a singularly dangerous player on the world stage.

A few months ago, Elon Musk was asked in an interview how he felt – with a net worth of roughly US$260-billion – being “the richest person on Earth?” Mr. Musk candidly countered, “I do think that Putin is significantly richer than me.”

Mr. Putin’s massive wealth remains shrouded in mystery: Nobody knows exactly how much “black cash” he has – nor where it is stashed.

In January, 2021, Mr. Putin’s most vocal opponent, Alexey Navalny, and his Anti-Corruption Foundation released an investigative documentary film titled Putin’s Palace: History of World’s Largest Bribe, an exposé of the US$1.4-billion Italianate palace on the Black Sea said to be the world’s largest private residence.

Within 24 hours of its release on Mr. Navalny’s YouTube channel, the video had more than 20 million views; it now has nearly 125 million.

In the aftermath of the exposé, Mr. Putin denied owning the property – which is reportedly more than 191,000 square feet, containing its own helipad, ice palace, church, amphitheatre, cinema, casino and hookah bar – and which is covered by an official state no-fly zone. A billionaire oligarch named Arkady Rotenberg farcically claimed he was the rightful owner. Leaked documents within the Panama Papers allege that Mr. Rotenberg, a childhood friend of Mr. Putin’s, maintains complex networks of offshore wealth for Russian political elites.

Mr. Putin has long cultivated the image of a gangster in the guise of a world leader. Back in 1999, several months before he took office as Russia’s President, Mr. Putin, then the country’s prime minister, stunned Russian speakers by declaring how his forces would deal with Chechen rebels: “If they’re in the airport, we’ll get them in the airport, if they’re in the toilets, we’ll get them there.”

The translator I worked with closely on The Last Boss of Brighton explained to me how that now-infamous remark was not accurately rendered in English.

It was a pivotal moment, he told me, because no Russian or Soviet leader had used such crude, street-level language before in public. They normally used highly structured official-sounding verbiage designed to bore the audience to sleep within minutes.

What Mr. Putin said about the Chechen rebels was, for want of a better phrase, “mob-speak.” Mafia talk. Rough street vernacular. The translation above is far too sanitized. What Mr. Putin said, rapidly, off-the-cuff, was that he would literally “grease them” – as in letting the Chechen rebels’ blood spill – “in an outhouse.”

In February, 2022, during a press conference at the Kremlin, standing at a podium beside France’s President Emmanuel Macron, Mr. Putin addressed Ukraine’s President, Volodymyr Zelensky with a shockingly tasteless verbal jab, saying that Ukraine must be made to implement elements of the 2014 Minsk Protocol.

“Whether you like it or not, deal with it, my beauty.”

That phrase is from a vulgar satirical song – known as a chastushka – popularized as Sleeping Beauty in a Coffin by the Russian punk band Krasnaya Plesen, or Red Mold.

Using the vernacular of a blatnoy – slang for a professional criminal – is part of the public persona, not just of Mr. Putin, but of his inner circle. When Russian Foreign Minister Sergey Lavrov was speaking recently to U.S. Secretary of State Antony Blinken about a potential treaty between the two countries, Mr. Lavrov said: “The boss said it; the boss did it. We will make sure that everything is done in good faith. However, the ponyatiya must also be respected at an international level.”

Ponyatiya is another loaded word – one that’s nearly untranslatable into English. Some media outlets rendered it as “agreements” or “commitments.” But this lacks both nuance and context. Before he served three stints in federal U.S. prisons for a variety of racketeering convictions Boris Nayfeld did three years in a Soviet zona – or prison work camp. There he learned to speak fenya – a criminal jargon with a deep and colourful history.

As Mr. Nayfeld explained to me, within the world of the vory v zakone – “thieves in law,” the highest-ranking criminals in the former Soviet Union – ponyatiya refers to “the unwritten understandings of behaviour in the underworld,” and has its origins among the vory v zakone in the time of Stalin’s gulags.

Imagine a Canadian prime minister, or U.S. president, publicly demanding that a foreign leader come to a “sitdown” or claiming that some politico in his circle had “made his bones.”

Is Mr. Putin’s gangsterism, then, merely the superficial posturing of a political strongman attempting to “sound tough”?

Hardly. Mr. Putin’s background as a street thug and his early involvement with violent organized crime figures has shaped his ethos. As a teenager, Mr. Putin – like Mr. Nayfeld – was a khuligan, a member of a violent street gang. More than a century ago, the Russian language appropriated the Anglo-Irish word “hooligan” – in Russian, it’s pronounced khoo-li-GAHN – to refer to street toughs and members of youth gangs.

Mr. Putin has proudly recalled it as time well spent in a “street university.”

Since Mr. Putin is not an especially big guy, standing about 5-foot-6 and 150 pounds, in his khuligan days he needed to contend with thugs who were considerably taller, heavier, stronger.

Back then, most people called him Volodya – a common diminutive of Vladimir – and he was known for harbouring grudges and for exacting violent revenge. “If anyone ever insulted him in any way,” one friend recalled in Masha Gessen’s book, The Man Without A Face, “Volodya would immediately jump on the guy, scratch him, bite him, rip his hair out by the clump – do anything at all never to allow anyone to humiliate him in any way.” Young Mr. Putin’s aggression became even more dangerous when, in his early teens, he began learning judo – eventually becoming a black belt – and the Soviet martial art of sambo.

Mr. Putin developed a curious technique in street fights: He’d jump on the backs of taller khuligans and start punching them in the face from behind. In other words, he learned the principles of asymmetrical warfare at a very young age.

Roland Freudenstein, vice-president of GLOBSEC, Central Europe’s biggest think tank, headquartered in Bratislava, has written that “much of Putin’s behaviour today can be explained by the core takeaways from those Leningrad years [as a khuligan] … including his uncanny ability to turn causality on its head and his keen sense of his opponents’ psychological weaknesses.”

After the collapse of the USSR, during his rapid rise to power as the deputy to Anatoly Sobchak, mayor of St. Petersburg, Mr. Putin worked hand-in-glove with one of the most violent mobsters in the former Soviet Union: Vladimir Kumarin, aka Kum, leader of the Tambovskaya Bratva – or Tambov crew – in St. Petersburg.

The two men were so tight that Mr. Kumarin was dubbed the “Night Governor” of St. Petersburg. Mr. Putin was said to rule the city by day, while the fearsome Kum ruled it at night. Like Mr. Putin, Mr. Kumarin is the consummate survivor: His right arm was amputated in 1994 after he was sprayed with machine gun fire during a failed hit.

Mr. Kumarin allegedly stole national assets of more than US$100-million. “Putin and Kum are tied to each other by blood and cocaine money, which were laundered via oil trade and other city projects,” according to businessman Maksim Freidzon, a Putin critic now living in exile in Israel.

But Mr. Kumarin eventually become a thorn in Mr. Putin’s side: an unmanageable criminal-oligarch. In 2007, Mr. Putin ordered his arrest. He airlifted commandos from Moscow in a full military operation to grab Kum, then flew him straight back to Moscow where he was tried and received a 23-year sentence for ordering killings, extortion, money laundering and fraud. He’s been languishing in high-security detention jails in Moscow.

“It’s unlikely that Kum will ever be released – at least not while Putin is in power,” Mr. Nayfeld told me. ”He knows far too much.”

Does any of this help us contextualize Mr. Putin’s current geopolitical behaviour? Does it help explain why he has initiated the largest ground war Europe has seen since the Second World War?

I believe so. Mr. Putin, like Mr. Nayfeld, had his world view forged in the decaying Soviet Union when theft from the state, bribery and other crimes were normalized behaviour.

In Russia today, as Steven “Seva” Kaplan, a Moscow-born New Yorker who hosts the largest Russian-language radio show outside Russia, told me: “The criminal world does what the police and the authorities are not capable of. Criminal groups are like a bridge between the part of the society which is not in cahoots with the police.

“Sadly, this behaviour is in our blood,” Mr. Kaplan said. “Russian democracy is so young that – yes, you can call it a ‘democracy’ but it’s turned into something ugly now, a piece of totalitarianism, some new kind of dark empire.”

Indeed, under Mr. Putin’s watch, it’s a new kind of criminal empire – one headed by a ruthless mob-like boss, the likes of which the world has never seen before.

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