39 — Benjamin Siegel

a.k.a: Bugsy

Occupation: Mobster

Born: 1906

Died: 1947

Brief Description:
Benjamin Siegel was born in Brooklyn to an ashkenazi jewish family. As a boy, he joined gangs and rackets which built up his lengthy criminal record. Eventually, he teamed up with Meyer Lansky who saw the need to start a jewish gang organized in the same manner as the Italians and the Irish. There, he got involved in bootlegging and hijacking and even served as the mob’s hitman.

Eventually, Siegel moved to California because he was in danger in New York and continued doing pretty much more of the same from extortion to racketeering. He ran casinos and a prostitution ring, all while befriending Hollywood movie stars and joining the highest circles of society.

During his time in California, Siegel was put on trial a few times. Although he was acquitted, it had significantly damaged his reputation so he sought to reinvent his personal image by diversifying into legitimate business with William Wilkerson’s Flamingo Hotel, a casino that would offer it all: gambling, the best liquor and food and the biggest entertainers. Eventually he coerced Wilkerson into selling all his stakes in the Flamingo.

Siegel went on a spending spree as he spared no expense on his casino and had huge cost overruns. On the opening day, the casino was still unfinished and so the opening was a fiasco: the celebrity guests were greeted by construction noises in a lobby still draped with drop cloths, the air conditioning broke down regularly and the luxury rooms were still not available. Two weeks later, the Flamingo shut down. And even though it reopened a couple of months later and began turning a profit, the mob bosses were growing impatient.

On the night of June 20, 1947, an unknown assailant fired at him through the window, hitting him many times, including twice in the head. During the hail of fire, Siegel’s left eyeball was blasted out, an unintended symbolic flourish for the man called the “visionary” who created Las Vegas. No one was charged with killing Siegel, and the crime remains officially unsolved.

Why he’s on the list:
Another mobster on my list. I started this blog with Al Capone who was a boyhood friend of Ben Siegel. So do I like mobsters? Not specifically. But I do like rulebreakers in general as every great idea or inventions came from challenging the norms and the accepted truths. And mobsters just happen to be pretty good at breaking the rules.

Like most notorious mobsters of his time, Siegel had a flashy style. He was making a lot of money and proudly flaunting it. And while this is something I doubt I would do, I’ve always enjoyed watching those who do as I find there is a certain beauty in the bluntness and vulgarity of showing off.

Even though Ben Siegel didn’t invent the Flamingo concept but merely stole the idea from Wilkerson, he is still considered the visionary behind the creation of my favorite city, Las Vegas. And it also serves as a reminder that coming up with good ideas is not as important nor as difficult as bringing your ideas to life.

The Flamingo cost a few millions and Siegel was killed for it. Over the years, the Flamingo generated billions. Yes, part of it is inflation but still. Let is serve you as a reminder not to let people take you down if they don’t share your vision.

40 — Shahrazad

a.k.a: Scheherazade

Occupation: Storyteller

Born: In tide of yore

Died: In time long gone before

Brief Description:
There once was a king named Shahryar. Upon discovering that the queen had betrayed him with a slave, the king sent for his Chief Minister, the father of the two damsels who (Inshallah!) will presently be mentioned and said “I command thee to take my wife and smite her to death; for she hath broken her plight and her faith. So the wazir carried her to the place of execution and did her die. Then King Shahryar took brand in hand and repairing to the Serraglio slew all the concubines and their Mamelukes. He also sware himself by a binding oath that whatever wife he married he would abate her maidenhead at night and slay her next morning to make sure of his honour; “For,” said he, “there never was nor is there one chaste woman upon face of earth.”

And so, he ordered his wazir to bring him a virgin to marry every day which he would then have executed the next morning before she could dishonour him. Three years later, the wazir couldn’t find any more virgins and returned home in sorrow and anxiety fearing for his life from the King. So his eldest daughter, Shahrazad, volunteered to marry the king.

Secretly, Shahrazad had asked her younger sister, Dunyazad, to join her in the king’s chambers at night and ask her for a story. Dunyazad did as she was asked and Shahrazad agreed and started telling a story which she stopped in the middle since dawn was breaking. So the king spared her life for one day so she could finish the story the next night. The following night Scheherazade finished the story and then began a second, more exciting tale, which she again stopped halfway through at dawn. Again, the king spared her life for one more day so that she could finish the second story. Thus the king kept Shahrazad alive day by day, as he eagerly anticipated the conclusion of each previous night’s story.

Eventually, after 1001 nights, Shahrazad told Shahryar that she had no more stories to tell. By that time however, the king had already fallen in love with her, so he spared her life permanently and made her his queen.

Why she’s on the list:
Shahrazad “had perused the books, annals and legends of preceding Kings, and the stories, examples and instances of by-gone men and things; indeed it was said that she had collected a thousand books of histories relating to antique races and departed rulers. She had perused the works of the poets and knew them by heart; she had studied philosophy and the sciences, arts and accomplishments; and she was pleasant and polite, wise and witty, well read and well bred.”

Shahrazad is the first fictional character on my list. And as a fictional heroine, her description will naturally be shaped to ideal standards that would please most readers, including myself.

And for the feminists out there, she should be a role model. She shows that women can actually control the men around them if they know how to properly wield their power to their advantage.

What I also like about Shahrazad is that she understands the power of a good story to entice an audience and always leave it wanting more. And since this is my first blog post after almost 10 years, I found it befitting to continue my little stories with the queen of storytelling herself. =)

41 — Leonidas I


a.k.a: Leonidas The Brave

Occupation: King

Born: circa 540 BCE

Died: 480 BCE

Brief Description:
Leonidas was the third son of Anaxandridas II of Sparta. His mother was his father’s niece and had been unable to bear children for so long that the King had to take a second wife. His second wife bore the king’s eldest son, Cleomenes. Shortly after however, his first wife gave birth to Dorieus and later to Leonidas.
Because Leonidas was not heir to the throne, he was not exempt from attending the agoge, which made him one of the few kings to have undergone the training.

(Sparta was an unusual city-state in that it had two kings simultaneously, coming from two separate lines, the Agiads and the Eurypontids. The agoge was the rigorous education and training regimen mandated for all male Spartan citizens, except for the firstborn son in the two ruling houses. Even though exempt however, they were allowed to take part if they so wished, which endowed them with increased prestige when they ascended the throne.)

After Anaxandridas’ death, Cleomenes ascended the throne but the spartans considered him insane and put him in prison where he committed suicide.
Leonidas then married Cleomenes’ daughter, Gorgo, and succeeded to the Agiad throne. (Dorieus had already died by then.)

In 481 BCE, he was chosen to lead the combined Greek forces to resist the Persian invasion and in August 480 BCE, he went out to meet Xerxes’ army at Thermopylae with a small force of 300 men. (Supposedly, the oracle at Delphi had predicted that Sparta would either fall to the Persians or mourn the death of a king.) Other Greek city-states joined Leonidas to form an army of 14,000. In contrast, Xerxes’ army consisted of over two million men according to Herodotus (but he’s known for exaggerating so take this with a pinch of salt).

Xerxes waited four days to attack, hoping the Greeks would disperse and eventually attacked on the fifth day. Leonidas and his men repulsed the Persians’ frontal attacks for two consecutive days and even killed two of Xerxes’ brothers. On the seventh day however, a Malian Greek traitor led a Persian general by a mountain track to the rear of the Greeks. At that point Leonidas sent away all Greek troops and remained in the pass with his 300 Spartans and a few hundred Helots and Thespians who refused to abandon him.

Now by this time the spears of the greater number of them were broken, so it chanced, in this combat, and they were slaying the Persians with their swords; and in this fighting fell Leonidas, having proved himself a very good man, and others also of the Spartans with him, men of note, of whose names I was informed as of men who had proved themselves worthy, and indeed I was told also the names of all the three hundred. – Herodotus

Why he’s on the list:
Of my favorite 50, Leonidas is perhaps the character that needs the least explanation as to why he’s on my list.
It should be pretty obvious and straightforward, but just in case you’re blind…
Leonidas embodies all the virtues of a charismatic leader (courage, respect, honor, loyalty, integrity, selflessness, etc.) even when challenged by insurmountable odds.
He and his men, through their valor and sacrifice, have set an inspirational example for all of Greece.
According to Plutarch, when someone told him: “Leonidas! How are you going with so few to risk with so many?”, he said: “If you think that I am going to fight by numbers, then the whole of Greece would be insufficient, for she is only a small part of the numbers of the Persians, but if I am going to fight by valor, then even this number is enough.”

And of course, as is usually the case, characters I like need to have that extra confidence/arrogance. =)
According to Plutarch (again), “When someone said to him: ‘Except for being king you are not at all superior to us’, Leonidas son of Anaxandridas and brother of Cleomenes replied: ‘But were I not better than you, I should not be king.'”

42 — Hernan Cortes de Monroy y Pizarro

Hernan Cortes

a.k.a: The Marquis of the Valley of Oaxaca

Occupation: Conquistador

Born: 1485

Died: 1547

Brief Description:
Hernan Cortes was born in Medellin, Spain, to a family of lesser nobility. Around the age of fourteen, he went to study at the University of Salamanca for a couple of years and soon after, in 1504, left Spain to seek his fortune in the New World.

As Cortes reached Santo Domingo, the capital of Hispaniola, he registered as a citizen and settled in the town of Azua de Compostela where he served as a notary for several years.
In 1511, he joined Diego Velazquez in an expedition to conquer Cuba. Velazquez was so impressed by Cortes that he secured a high political position for him in the colony. As time went on however, the relationship between the two became tense and, in 1518, as Cortes was about to lead an expedition to Mexico, Velazquez changed his mind and revoked his charter. But Cortez ignored the order and set sail for Mexico anyway with 500 men, 11 ships and 13 horses.

Cortes became allies with some of the native peoples he encountered, but with others he used deadly force to conquer Mexico. He fought Tlaxacan and Cholula warriors and then set his sights on taking over the Aztec empire. As the Spaniards reached the Aztec capital, Tenochtitlan, they were received with open arms by Moctezuma II, the ruler of the Aztec empire, who thought Cortes to be the feathered serpent god, Quetzalcoatl, because he was of lighter skin, sitting on his horse and wearing metal armor. Nonetheless, Cortes took Moctezuma hostage and his soldiers raided the city. Led by Cuauhtemoc, Moctezuma’s nephew, the Aztecs rallied. Though reinforced, the Spaniards were besieged, then routed as they fled but they were soon back, and laid siege in turn. They finally took the city in 1521 and claimed it for Spain.

As a result of his victory, King Charles I of Spain (aka Charles V, Holy Roman Emperor) appointed him as governor, captain general and chief justice of the newly conquered territory, dubbed “New Spain of the Ocean Sea” but Cortes faced challenges to his authority and position. He traveled to Honduras in 1524 to stop a rebellion against him in the area. Back in Mexico, he found himself removed from power so he traveled to Spain to plead his case to the king but he was not reappointed to his governorship.

In 1540, Cortes retired to Spain and spent much of his later years seeking recognition for his achievements and support from the Spanish royal court.

Why he’s on the list:
I first heard about Cortes in my early adolescence. I didn’t know much about him at the time but the fact that he was a soldier, an explorer and an adventurer was enough to fuel my imagination.
As I grew a older, it was Cortes’ determined character and pioneer spirit that impressed me. He was willing to do anything to reach his goals. In one instance, he even scuttled his ships in order to eliminate any ideas of retreat among his men.
Today, as I am writing this, it’s his insatiable greed for gold, his desire to always have more, that fascinates me. It’s what capitalism is all about and I love it.

That being said, none of the points above would stand alone to put Hernando Cortes on this list. He’s on this list because he’s a character I liked for different reasons at different stages in my life. For me, he’s a reminder of how our vision of the world grows and evolves over time throughout our experiences, sometimes for the best, sometimes for the worst…