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Soviet rule brought a new wave of official violence. Josef Stalin executed nearly all of his senior-most comrades from revolutionary days, almost his entire upper echelon of military officers, and millions of others when one included deaths in labor camps and from forced collectivization. Stalin was Ivan’s natural heir, and said as much himself. During the darkest days of Hitler’s invasion, Stalin could be found scribbling the words “teacher, teacher” on the pages of a biography of Ivan. He “constantly compared his terror to Ivan’s massacre of the boyars”—the landed aristocracy—according to a biographer of the twentieth-century dictator. Stalin thought that Ivan’s only fault was that, in slaying the boyars, “he should have killed them all, to create a strong state.”

One of the most credible and revealing accounts of Stalin’s time is Special Tasks, the memoir of Pavel Sudoplatov, who directed overseas assassinations for the dictator. Contemplating his own and others’ acts during the Soviet era, Sudoplatov wrote that “victorious Russian rulers always combined the qualities of criminals and statesmen.” Indeed, his book is a dispassionate catalogue of official poisonings, stabbings, and other plots, including the killing of his first victim, Yevhen Konovalets, a Ukrainian nationalist whom he cultivated for five years before blowing him up in Germany with a booby-trapped box of chocolates. Sudoplatov played a leading role in one of the most infamous political assassinations of the twentieth century, that of Leon Trotsky. The revolutionary leader had fled to Mexico after earning the enmity of Stalin, who ordered Sudoplatov to make his slaying a priority. So in 1940, Ramon Mercader del Rio, a Spanish national working for a Sudoplatov deputy, dispatched him with a pickax to the head.

Musa Eitingon Malinovskaya is the daughter of Mercader’s supervising agent, the legendary Soviet master spy Leonid Eitingon. Dressed in a silk scarf and a denim blouse for coffee at an upscale Moscow café, the sixty-year-old Malinovskaya told me how, as a teenager in the 1960s, she shared ice cream with Mercader and her father. She had no idea who he was, nor of her father’s role in the Trotsky assassination, but the two men had an evidently warm relationship. “My father introduced him to me as ‘my friend from the Spanish resistance,’” Malinovskaya said. “…I heard about him killing Trotsky only in 1989 when I read about it in Literaturnaya Gazeta.” Malinovskaya was clearly proud of her mother, Musa, for whom she was named. She showed me a 2005 advertisement featuring a 1935 photo of her mother as a gorgeous twenty-two-year-old Army parachutist. But she was singularly devoted to her father and eager to talk about his association with Trotsky’s slayer. One got the impression that it was the most important thing she could say about herself. The murder perhaps helped to break the ice at cocktail parties.

In 1954, a Sudoplatov protégé named Nikolai Khokhlov became the first Soviet defector to publicly divulge firsthand knowledge of the Kremlin’s assassination program. He became a valuable source of intelligence for the CIA and survived an attempt by Russian agents to assassinate him using radioactive poisoning. The West usually prosecutes its traitors but, as Khokhlov was witness, the Soviets regarded them as fair game for murder.

Another defector, Bulgarian novelist and playwright Georgy Markov, died in a most exotic way. He was working as a London-based journalist for the BBC when Moscow and its Bulgarian allies joined forces to kill him. In 1978, an assassin jabbed a tiny ricin-laced pellet into Markov’s thigh as he waited at a bus stop near Waterloo Bridge. Although the murder weapon wasn’t found, an excited British press reported that the pellet was fired from an umbrella, and that idea stuck with historians.

Following the collapse of the Soviet Union, Russia became a fledgling democracy in 1991. It should have been an opportunity for the nation to demonstrate that murder and mayhem were not embedded in the Russian DNA, that the notion of a centuries-long continuum of violence was fatally flawed. The czars and the dictators were gone; tyranny no longer ruled the land. But its people quickly learned that democracy Russian style could be ruthlessly bloody. A historic tradition seemed to be reasserting itself. The chosen style of rule—tyranny or democracy or something in between—seemed to matter little.

There were, of course, differences between the old and the new. Ivan, Peter, and Stalin alike reserved the right to decide who would live and who would die. Ivan and Peter tortured their unlucky victims to death, and Stalin had them shot in the back of the head or sent to prison camps to be starved and worked to death. This was state murder. But none of these three strongmen permitted murder in the streets. On the contrary, they were very nearly pathological about order and concealing Russia’s dark side from the rest of the world.

Under the rule of Boris Yeltsin in the 1990s, the old order was turned upside down. There was little if any state-sponsored murder. But contract killers brazenly murdered prominent bankers, metal traders, oilmen, and hundreds of others for violating unspoken “rules of the game.” Kidnappers chopped off the fingers and heads of their victims, sometimes before even requesting a ransom. Russia’s richest billionaires, known collectively as the oligarchs, left a trail of dead bodies—by coincidence or otherwise—as they accumulated unimagined wealth; these victims were often business rivals. The state solved few cases, and in that way seemed an accomplice to some of them.

But if Yeltsin, the nation’s first popularly elected president, appeared to tolerate the bloodbath, it wasn’t his creation. Rather, it filled the vacuum created when the once-feared KGB and other law enforcement agencies seemed to vanish in the unraveling of the Soviet Union. Grievances that previously would have been forgotten or settled through legal or other peaceable means suddenly poured into the streets. Bitter scores were settled in shootings carried out directly by, or ordered by, swindled business partners, gangs denied a piece of the action, and so on. The murders and murderers were cold-blooded and had unmistakable attitude. Bankers were among the most frequent victims because of their access to money; scores of them were killed in shootings, bombings, and at least one poisoning during the 1990s.

Lesser citizens also could be caught in the cross fire. In summer 1993, three gunmen murdered a café manager and then, at a kiosk where they found service unsatisfactory, shot a saleswoman and a customer dead. In April 1995, two gunmen killed a Russian stockbroker’s six-year-old daughter, who was on the way to kindergarten. And in November 1996, a bomb buried in a Moscow cemetery killed some dozen mourners. Organized crime became Big Business. Experts said that more than four-fifths of Russia’s banks were controlled by gangs, whose tentacles spread west to Israel, Europe, and the United States. These Russian gangs poured into Germany, for example, bringing with them the most grisly crimes the country had experienced in decades. In a 1994 case, German police came upon the bodies of a bordello owner, his wife, and four prostitutes, all of them apparently killed by a Russian gang. Police agencies such as the U.S. Federal Bureau of Investigation said they had never faced a challenge so difficult, a shadowy underworld that had come to be known as the “Russian mafia.”

As the 1990s drew to a close, Yeltsin retired from the presidency. He was succeeded by a former KGB spy catapulted into office by powerful men confident that they could manipulate him—but who would turn out to be wilier than any of them. Once again, Russia would be ruled by a strongman.