Episode Six – Ivan the Terrible versus Lucky Luciano

Today’s dustup is from the Villains bracket and is one of the more unusual matchups. It pits one of history’s most feared men, Ivan the Terrible versus a man who created a crime syndicate that controlled vast swathes of many major cities of the United States, Charles “Lucky” Luciano.

Ivan the Terrible
Ivan the Terrible

Ivan Vasilyevich, later known to the world as Ivan the Terrible, was the son of Vasili III, the Grand Prince of Moscow and his second wife, Elena Glinskaya. He was the first child born to the pair who had desperately been trying for a son or for that matter any child for four years. That is until on the evening of August 25, 1530; a boy was born to the royal couple, a son named Ivan. In many a chronicle of the time, it was noted that huge storms erupted that evening throughout Russia, a foretelling of a tempest about to take place throughout the land. It is apropos that storms were to erupt because the name was later given to Ivan, Grozny, derives its root from the word grom, meaning thunder. 

When he was just a mere three years of age, on December 3, 1533, Grand Prince Vasili, died. This left Ivan as the new Grand Prince in name only. For years he was treated like a puppet. Guards surrounded the boy, not because of a threat from others outside his entourage, but because of the many threats within, from his uncles and cousins, the hundreds of Princes, and from the boyar families who saw a way to absolute power. Boyars are similar to Counts or Dukes in the West. Many powerful boyar families were exceedingly wealthy in Russia at the time, and they had considerable influence over internal affairs.

Ivan was routinely abused and shunned during his youth which left indelible scars on the young Ivan. There are reports of his torturing and murdering animals growing up, a sign of deep-seated psychosis which was to manifest itself in the years to come.  

Ivan’s education was handled by carefully selected priests, and from all accounts, Ivan was an excellent student. He was a voracious reader with a passion for history, especially the historical accounts of the great leaders of the past, like Augustus, Alexander the Great, Julius Caesar as well as famous Russian rulers such as his Alexander Nevsky, Dmitri Donskoi and of course his grandfather, Ivan the Great. Sadly, his only playmate was his deaf-mute brother Yuri.

He was being controlled by the many boyars or noble families of the time, but by the age of 13, he finally had enough. He had one, a Prince Andrey was taken prisoner and had him literally thrown to the dogs. It was the first murder ordered by Ivan, indeed not the last. 

Next item on his agenda was to find a bride. The one chosen amongst many was a young lady by the name of Anastasia Zakharin, also known as Anastasia Romanovna. Yes, this is the first time we hear this name in prominence in Russian history. They were to wed on February 13, 1547

Anastasia was to be the love of his life so when she died in 1560; he was devastated. It is about this time that we begin to see the dark side of Ivan as his wife had a remarkable ability to calm the anger that brewed within. After her death, the Tsar was to have a total of six other wives, many of whom were never accepted by the dominant Russian Orthodox Church.

Between 1547 and 1560, Ivan brought forth many reforms to Russia including the Sudebnik of 1550 which was a series of law reforms started under his father, Vasili. He created a standing army known as the Streltsy, established a kind of Russian parliament known as the Zemsky Sobor, but he also created laws that would restrict the movement of peasants. This would lead to the creation of a slave class, known as serfs which would fully vest itself in 1597 under then Tsar, Boris Godunov.

During this period, Ivan led his armies to several important wars and battles that was to help shape modern Russia. The two most important were the conquests of Kazan and Astrakhan. These two fortress cities were parts of the remnants of the Mongol horde, now known as the Tatars. His defeats of these two strongholds lifted some of the centuries long raids upon the peoples of Russia, which caused tens of thousands, maybe hundreds of thousands to be captured and sold into slavery.

The early years of Ivan IV looked pretty good. Then came Anastasia’s death, which he blamed on poisoning by the cursed boyars. Now hell was to be brought forth on Russia.  Being the shrewd man that he was, Ivan didn’t just go out and ravage the nobility and the people, no, he resigned from his post as leader of Russia.

Feeling rudderless, the boyars agreed to all of the demands that Ivan made to return as the ruler of Muscovy as it was known then. When he returned to Moscow, he unleashed what is known as the Oprichnina. 

Using his six thousand-man secret police force known as the oprichniki, Ivan terrorized the boyars, in particular, taking away their lands if he or anyone in the oprichniki thought them to be disloyal. Along with executions, we have the torture of thousands of Russians, many in retribution for the years of abuse the young Ivan went through. This was one of the first, but certainly not the last, periods of terror that would befall the Russian people.

Lasting about seven years, the oprichnina, based on the paranoia of Ivan, all classes of Russian citizens were targeted, especially the landowners. The self-proclaimed tsar of all Russia saw conspiracies behind every corner. Executions, often, were welcomed by the victims after the excruciating tortures, sometimes attended by and personally guided by Ivan himself. 

The oprichnina ended in 1572, a year after the disastrous invasion of Moscow and its burning by the Crimean Tatars, a group Russia had still not subdued. Ivan saw this as an example of how ineffective the oprichniki were as they gave little resistance to the invaders. That and the reign of terror accomplished what the tsar wanted, autocratic and unquestioned power.

His unbridled violence towards his people gave him the name of the Terrible, or Grozny, which, if adequately translated more closely becomes, the Awesome or Fearsome. His reign of terror and the numerous wars, some successful, many not, emptied the coffers of his country’s treasury. This and his murder of his son and heir to the throne, Ivan Ivanovich in 1581, would lead to the Time of Troubles, which was to cause untold suffering to the Russian people and bring the country to as close of a state of collapse as would occur throughout its history. 

When he died in 1584, Ivan left only one legitimate heir, the feeble-minded Feodor, who when he died, would end the line of Russian rulers that went back all the way to the Varangian invader Rurik, in the year 860. His legacy includes the autocratic legacy that plagues Russia to this day.

Time for the Putting it Into Perspective segment which I will do for Ivan and not for Luciano, as he is a 20th Century person.

During the reign of Ivan, the Knights of Malta are formed. Henry VIII marries Anne of Cleaves. The first European contact with Japan is made by Portuguese sailors blown off course from China. Queen Elizabeth I of England is crowned at Westminster Abbey, and Sir Walter Raleigh’s men discover Roanoke Island in what would become the state of North Carolina.

Next up we have a man born, Salvatore Lucania on November 24, 1897, in Lercara Friddi, Sicily, Italy, better known to the world as Charles “Lucky” Luciano. 

Lucky Luciano
Lucky Luciano

Luciano arrived in the United States in April of 1906 when he was only nine years old. The family settled down in one of the Italian neighborhoods in New York City, the Lower East Side of Manhattan. By the age of 14, Charles had decided to drop out of school, trying his hand at a legitimate job delivering hats for $7 a week. After winning 244 dollars at a dice game, a considerable sum of money at the time, he decided that the life of crime was for him. His parents were appalled and sent him to a school for truants in Brooklyn. Luciano didn’t stay there very long.

When he became a teenager, Lucky joined the Five Points Gang. This was to be a real educational period for the young boy and a place where he would meet a number of future mob associates like Al Capone, Johnny Torio, Vito Genovese, Frank Costello and his good friend, Meyer Lansky.

His big break came on January 17, 1920, with the ratification of the Eighteenth Amendment to the U.S. Constitution which was to enter the country into the age of Prohibition. This act prohibited the manufacture, sale, and transport of alcoholic beverages throughout the country. It was a billion-dollar gift to organized crime, and Luciano took full advantage of it.

During this time, Lucky, whose moniker was given to him for reasons that are somewhat murky, worked under Arnold “The Brain” Rothschild, the man who fixed the 1919 baseball World Series. He was to show Luciano how to run a criminal operation like a business. By 1925, it was estimated that the Sicilian immigrant was racking in a cool $4 million a year, after bribes to police and judges which was thought to be more than $20 million a year.

The two major mafia bosses at the time were Joe Masseria and Salvatore Maranzano. The animosity between the two men instigated the bloody Castellammarese War which lasted for 14 months starting in February 1930 and ending in April of the following year with the assassination of Joe “The Boss” Masseria on April 15th. Many believe that Lucky Luciano orchestrated the killing to end the senseless war between the two leaders also known as Mustache Pete’s.

Maranzano was likely in on the hit as well as he had offered a reward to Lucky for turning on his boss. But true to the way the Mustache Pete’s operated, Maranzano reneged on the deal feeling threatened by Luciano, even going so far as to put a price on his head by ordering a hit on his underboss.

Having been given a heads up by his friends, about his impending murder, Lucky turned on his new boss and had him assassinated on September 10, 1931. The assassins included Jewish mobsters and longtime friends, Bugsy Siegel and Red Levine.

Lucky Luciano was now considered the boss of bosses or capo di tutti capi, but it was a title he turned down. Instead, he created an organized crime syndicate known as the Commission which consisted of the five New York mafia families along with one from Chicago and one from Buffalo, New York.

The first seven members of the original Commission were Luciano, Vincent Mangano, Tommy Gagliano, Joseph Bonnano, and Joe Profaci from New York, Al Capone of Chicago and Stefano Magaddino of Buffalo. 

These seven men, along with their criminal associates, were to expand their criminal enterprises after the repeal of Prohibition to include extortion, bookmaking, loan sharking, gambling, drug dealing and murder for hire in most of the major cities throughout the United States. They were racking in billions of dollars. By the early 1930’s they were one of the wealthiest enterprises in the country, rivaling, as they put it, U.S. Steel.

Things were certainly looking up for Luciano until the governor of New York appointed a special prosecutor to look into the activities of organized crime, one Thomas E. Dewey.

Dewey concocted an indictment against Luciano by arresting over 100 prostitutes and pimps, having their bail set at an amount they could not hope of paying and putting pressure on them to give up their supposed boss. A few caved into the pressure, and they made up stories that Lucky was their ultimate boss, and the ringleader of the prostitution rings in New York City. It was actually David Betillo who ran things, and he was indicted as well. It was considered beneath Luciano to actually run the brothels although he most certainly received monetary gains from their operations.

Whatever the truth, Lucky Luciano was found guilty on all 62 counts against him. He was sentenced to 30-50 years in prison. That didn’t stop his criminal activities though. From his cell first at Sing Sing in Ossining, New York and later at the depressing Clinton Correctional Facility at Dannemora, he continued to run his organization, first through Vito Genovese until his escape to Italy to avoid a murder rap, then through his other associate, Frank Costello.

After all of his appeals were rejected, despite recantations of much of the testimony, Luciano stepped down as the boss of his crime family. But as luck would have it, yes, I know bad pun, the United States entered World War II.

Because of the influence, the Mafia had on the dockworkers on the eastern seaboard, and after the unusual sinking of the SS Normandie in the Port of New York, Luciano was approached by Naval Intelligence for his help. They gave Lucky improved accommodations for his aid in keeping the docks safe and protected. He also helped the British and Americans through his contacts in Sicily when Allied forces invaded the island in 1943, known as Operation Husky.

For his aid in the war effort, Luciano’s sentence was commuted under one proviso; he had to leave the country, being deported to Italy, never to come back to America as he had entered the country illegally. This hurt Lucky to his core.

Arriving in Naples, Italy on February 28, 1946, Luciano had no thought of retiring from his life of crime. In October he went to Cuba to attend a major mob meeting known as the Havana Conference. He stayed in Cuba afterward, trying to run his old operations from there. The United States authorities learned of his move and put pressure on the Cuban government to expel him which they did.

On his return to Italy, he was constantly under surveillance as the authorities knew of his many criminal activities. When Luciano died on January 26, 1962, at the Naples International Airport, he was about to be picked up and arrested for drug smuggling.

Lucky Luciano was a cold-blooded killer, criminal mastermind but also a shrewd businessman. He was also one of the most feared men in America who could order you killed as easily as ordering a sandwich from the deli counter.

Now for the scoring.

First up I will be seeing who deserves the big 40-point score on how bad they treated the people in their time and country.  While Lucky Luciano was as brutal of a gangster as they come, he fails to match the absolute evil nature of Ivan the Terrible. Ivan actually enjoyed watching his victims suffer through the torture he put them through and had far, far more people killed than Lucky. For that reason, I will give Ivan the full 40 points. Luciano though was pretty damned nasty himself, so I’ll award him 35 points.

The second score is 25 points for their lasting effect on history. Luciano was the mastermind and founder of an organization, La Cosa Nostra or the Mafia, that would control vast swathes of America for decades, with the remnants still apparent today. Ivan IV began a system of attaching people to the land which would enslave millions of peasants, fellow Russians for centuries. For this, I have to give 25 points to Ivan and 18 to Luciano. 

Next up is the 20 points for their on overall history. Outside of their country, both men had influence, but Ivan comes out on top again because of the wars he had waged against his many neighbors. For this, I give him the full 20 with Luciano receiving 18, mostly for his aid to the war effort.

Finally, we have the 15 points for the time that the two men were villains. For Luciano, we have a span from 1916 until his death in 1962, 46 years. Ivan, for his part, began his reign of terror with the death of his wife Anastasia in 1560, ending with his death in 1584, 24 years. Given their time, Luciano gets 15 points and Ivan 10.

The final score is Charles “Lucky” Luciano with 86 points but Ivan the Terrible scores a whopping 95 points which gives him the win, moving on to the second round where he will face another notorious villain from history. That person will be either the Roman Emperor Caligula or the head of Unit 731 during World War II for Japan, Shiro Ishii.

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Mark Schauss has been podcasting for over 8 years. His Russian Rulers History was a top history podcast for 7 1/2 years. Discover his new entry into the podcast world.



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