Top 10 Most Expensive Historic Paintings in The World

It can be baffling how much a historically significant work of art can go for at auction. Not everybody gets it, but then again not everybody can afford the perspective of a millionaire. For anyone interested in some of the most remarkable and expensive paintings ever sold, we created this list of truly exceptional pieces.

From portraits to landscapes and abstract creations, all paintings have a story to tell. They talk about an era, but most of all about the artists behind them. Every work of art on this list is accompanied by a few key facts about its maker, who more often than not was underappreciated during his lifetime. Centuries later, however, these masterpieces ended up fetching millions of dollars at public and private sales which only the privileged got to attend.

When Will You Marry?

It never ceases to amaze us how little-appreciated some artists are in their lifetime and then how incredibly expensive their works become long after their demise. The When Will You Marry? Post-Impressionist oil painting by Paul Gauguin represents one of the most spectacular such stories of late fame: it recently became the world’s most expensive piece of art. [Update: A legal dispute has revealed that a painting thought to be the world’s most expensive artwork is not the most expensive one after all. Paul Gauguin’s 1892 oil painting “Nafea Faa Ipoipo (When Will You Marry)?” sold for $210 million in 2014, $90 million less than originally reported]

About Paul Gauguin

Eugene Henri Paul Gauguin had a strong influence on iconic artists such as Henri Matisse and Pablo Picasso. However, this only happened after his tragic death (morphine overdose) in 1903. During his life, the French Post-Impressionist artist did not manage to raise much interest, though he tinkered with various arts: sculpture, ceramics, print making, painting, and writing.

He was initially a successful stockbroker, during which time he earned a lot of money from both brokering and art dealing. However, the Parisian stock market suffered a great blow in 1882 and crashed, which led to the quick deterioration of Gauguin’s personal wealth. Shortly afterwards he decided to become a full-time painter.

His decision affected his relationship with his Danish wife and her family, who eventually decided to banish him for not staying true to their middle-class values. His vision of romance and realty gradually deteriorated to the point where the artist started to see the world through his own made-up fictions.

As an example, Gauguin tried to portray Tahiti as a place where people spent their time doing nothing else but sing and make love. He did so both in his paintings and in a book that he later wrote to describe his adventures in the French Polynesia. Neither his paintings nor his writings enjoyed any real success in his lifetime, and he eventually ended up bitterly disappointed by reality. His talent and artistic influence were only later fully recognized.

The French artist who created it did not enjoy much attention during his life, and yet this painting was sold to an undisclosed buyer for approximately $300 million (the exact sum has not been revealed). The image depicts two Tahitian women, and it used to be on loan at the Kunstmuseum in Basel for nearly half a century.

During that time it was owned by the family of Rudolf Staechelin, one of the most important Swiss art collectors of the early 20^th century. Experts believe the buyer to be Qatar Museums, but the painting will only be delivered to its new owner in January 2016.

When Will You Marry? by Paul Gauguin

The Card Players

Painted in the early 1890s, The Card Players series by Paul Cezanne was completed during the artist’s so-called final period, in which he created some of his most acclaimed works. There are five final versions of the scene, all showing Provencal peasants focused on the game of cards. The number of subjects and the size of the paintings varies, but the final three are very similar in composition, showing only two men.

About Paul Cezanne

Recognized as the father of all 20^th century artists by masters such as Picasso and Matisse, Paul Cezanne represents the artistic bridge between the 19^th century Impressionism and the radically different tendencies of the following century, especially cubism. Like many great artists, he was initially misunderstood by the public, but his desire to break from norms and to freely express himself kept him going. He eventually completely grew out of the conventions of the time.

His exploratory and repetitive brushstrokes are instantly recognizable, and his works show his dedication to understanding human visual perception. Cezanne was preoccupied with the simplification of forms and their reduction to basic geometric shapes such as spheres, cylinders and cubes. He was also fascinated by optical phenomena and tried to render binocular vision in graphic form by painting slightly different visual perceptions of the same subject.

His visual explorations opened a new path for the younger artists of his time and for the ones who followed. In order to achieve a “lived perspective”, Cezanne renounced essential classic artistic concepts, such as single view perspective, pictorial arrangements, and even outlines, which in his vision simply enclosed color. This tendency of altering the objects in order to capture the complexity of what the eye naturally sees later evolved into even greater distortions and eventually into form fracturing as seen in the iconic works of Picasso.

One version was sold in 2011 for a record price, and even though the exact sum has never been disclosed, it is believed to be the second most expensive painting ever sold, estimated to have fetched between $250 and $300 million. The buyer was the Royal Family of Qatar.

A number of drawings and sketches were made in preparation for this project. Over a dozen studies paved the road for the final five pieces, but there is no way to tell for sure what the exact order of completion for each painting in the series was.

The Card Players by Paul Cezanne

No. 5, 1948

Often described as a “dense bird’s nest”, No. 5, 1948 is a record-breaking painting by famous American abstract expressionist Jackson Pollock. Its first ever buyer was Alfonso A. Ossorio, who paid $1,500 for it back in 1948. If that sum doesn’t say much to you today, $140 million certainly will. That is how much the painting went for at a 2006 sale, when an unknown buyer added it to his or her collection.

About Jackson Pollock

The unique drip painting technique is instantly recognizable as a Jackson Pollock trademark. You don’t need to be an art connoisseur to know the name behind the iconic No. 5, 1948 painting, as well as all the others in the series.

This totally innovative way of creating art is what Pollock is most famous for as a contributor to the abstract expressionist movement of the 1940s. He first discovered liquid paint in 1936 during a workshop in New York City. This opened a new door for the artist’s creative spirit and he soon started using synthetic resin-based paints, which represented a completely unconventional medium at the time.

He also ditched the traditional art tools and replaced them with pretty much anything that met his creative needs: sticks, hardened brushes, basting syringes. Pollock discovered that sturdier surfaces such as walls and floors worked better for his art than the conventional easels. By placing his canvas on the floor he had the privilege of working on his paintings from various angles and he could even “literally be in the painting”, as he himself pointed out.

Pollock was known to completely disconnect from the environment and everything that was going on around him while he worked. “When I’m in my painting, I’m not aware of what I’m doing”, he said. His painting technique had him constantly move around the canvas in a dance-like manner searching for the right angles from which to add new dimension to his creations. Contrary to what some may believe, his drip paintings were not the result of accidents, but of purpose-driven actions, as well as a complete lack of fear to experiment and adjust while in the middle of the creative process.

This is not only a prime example of very expensive abstract art, but also the most expensive Jackson Pollock ever sold. Prohibitive as that price may be, it is actually completely justified in the world of arts. The rarer a painting is, the more expensive it is going to be.

Also, pieces that have had a significant impact on the evolution of art and the birth of new movements are always going to be more valuable than ordinary ones, and Pollock’s No. 5, 1948 definitely embodies the essence of a new artistic era called abstract expressionism. Plus, the painting is the only one from the artist’s drip series that is not safely displayed in a museum, which makes it incredibly covetable among art collectors.

No. 5, 1948 by Jackson Pollock

Le Reve (The Dream)

One of the most expensive oil paintings currently in private hands, Le Reve is a 1932 creation of Pablo Picasso. The world-famous Spanish artist was 50 years old when he painted this, and the young lady in the picture was his 22-year-old mistress Marie-Therese Walter. While distorted characters were very common in the painter’s depictions at the time, some people believe that the dramatically tilted head of the woman was intentionally drawn so as to resemble an erect penis – arguably symbolizing Picasso’s passionate feelings for his lover.

About Pablo Picasso

While Pablo Picasso’s cubist paintings may suggest that he actually did not know how to properly draw, one would be very far from the truth to assume that. Picasso was born in a middle-class Spanish family which valued art very much: his father was a painter, and young Pablo’s first word was a shortened version of the Spanish word for pencil.

His drawing skills were remarkable even from an early age, so starting at age seven he began to receive formal artistic training from his father, who believed in the traditional academic ways of teaching art. By the time Pablo was 13 years old, his master already felt surpassed by his son’s talent and precise technique.

At age 16, the young artist was sent to Madrid’s Royal Academy of San Fernando, which was the best art school in the country. Formal education, though, did not satisfy Pablo Picasso’s need for freedom of expression, so he gradually strayed from traditional techniques, creating his own set of rules.

He became famous for developing and exploring a variety of new styles, such as constructed sculpture (assemblage), collage, and cubism. The latter represents what Picasso is most famous for: an avant-garde movement which he co-developed together with George Braque. Highly prolific, Picasso became widely appreciated for his revolutionary views and accomplishments, and gained remarkable fame and fortune – something that very few artists have the privilege to experience in their lifetime.

With oversimplified shapes and bold contrasting colors, Le Reve last changed hands in 2013, when Steven A. Cohen paid $155 million for it. The seller was Steve Wynn, a casino magnate with poor peripheral vision. That last detail is relevant because it led to the accidental damage of the painting in 2006: Wynn put his shoulder through the canvas, tearing a six-inch hole into it. After paying $90,000 for repairs and having some insurance troubles, he was finally able to sell the painting to Cohen, making Le Reve the most expensive Picasso.

Le Reve (The Dream) by Pablo Picasso

Garcon a la Pipe (Boy with Pipe)

Another famous Picasso, Garcon a la Pipe is a 1905 creation that belongs to the artist’s Rose Period. It shows a teenage boy wearing a wreath of flowers and holding a pipe, but the identity of this young man has remained unknown. The artist himself (24 years old at the time) was very vague about it, which suggests that he either didn’t know the boy, or didn’t want people to know who he was.

The creative process involved lots of posing, during which time Picasso had the young man changing positions from standing up to leaning against a wall and finally sitting. The exact placement of the hand holding the pipe was also a detail that took a lot of preparation.

The artistic and historic value of the painting is not really significant, but it has still managed to fetch over $104 million at a Sotheby’s auction in 2004, simply because it is a Picasso. Experts have even been disappointed by “how much the marketplace is divorced from the true values of art”, as curator Pepe Karmel put it.

Garcon a la Pipe (Boy with Pipe) by Pablo Picasso

The Scream

The original name of the painting is actually The Scream of Nature, but it is better known as simply The Scream by Edvard Munch. The Norwegian expressionist artist created four versions of the work – using tempera, pastel, and crayon– between 1893 and 1910.

About Edvard Munch

The painting for which Edvard Munch is most famous actually embodies the essence of his artistic direction and even of his personal story. The popular name of the paining is The Scream, and it depicts a troubled person whose expression and figure are distorted by pain or agony.

Growing up without a mother (she died when Edvard was very young) and with an overly-religious father who struggled with mental illness, the artist struggled with fear of hell, death and insanity for all of his life. A series of family tragedies marked his development in a deep way, with one of his sisters dying of tuberculosis at age 16, another sister being institutionalized in a psychiatric institution, and his only brother dying at age 30, only a few months after getting married.

In 1886 Munch finished the first rendition of a painting called “The Sick Child”, which showed his teenage sister on the deathbed next to a grieving woman with her head bowed in sorrow, seemingly for not being able to help the child. This was the artist’s first work for which he left behind the norms of realist representations and used his brushstrokes to express emotions rather than objective realities.

The painting was not received well by critics at the time, but Munch continued to explore this new way of expression and later became a world-renowned initiator of Expressionism: a modernist movement that focused on representing reality solely from a subjective perspective. The physical world becomes less important in an expressionist’s art, and it is even distorted in order to evoke moods, ideas and feelings. Munch’s real success only occurred when he started creating art in this novel and inspiring way.

The composition depicts a sexless screaming person with a movingly agonized expression. The person appears to be standing on a bridge, with a deep orange and red sky in the background. The artist explained his source of inspiration in a hand-painted poem that he placed onto the frame of one of the pastel versions:

“I was walking along the road with two friends – the sun was setting – suddenly the sky turned blood red – I paused, feeling exhausted, and leaned on the fence – there was blood and tongues of fire above the blue-black fjord and the city – my friends walked on, and I stood there trembling with anxiety – and I sensed an infinite scream passing through nature.”

The 1895 pastel-on-board version set a new record price in 2012, when it was sold by Sotheby’s for $120 million. Much more expensive paintings have gone under the hammer since then, but at the time that was a huge price for a painting that was originally expected to fetch around $40 million.

The Scream by Edvard Munch

Woman III

For non-connoisseur of art, Woman III is probably one of the strangest and most expensive paintings out there. For passionate collectors, it is a covetable masterpiece which rightfully fetched $137.5 million when it last went on the market in 2006. The buyer was Steven A. Cohen, and the inflation-adjusted price puts it at number 4 on the world’s most expensive paintings list.

Expressionist painter Willelm de Kooning created six versions of it between 1951 and 1953, all inspired by his wife. She became his muse after they first met in 1950, and thus the iconic Woman series began. Highly reminiscent of Picasso’s deconstructive portraits, these works are prime examples of abstract expressionism.

About Willem de Kooning

With a very unique style of painting, Willem de Kooning was one of the visionary artists that formed what became known as the New York School – an informal group where American musicians, painters, dancers, and poets of the 1950s and 1960s created freely, drawing inspiration from avant-garde movements such as surrealism, action painting, experimental music, jazz, and improvisational theater.

De Kooning’s style became known as abstract expressionism, with his iconic black-and-white series (painted approximately between 1946 and 1949) playing a very important role in the history of the movement. While most people don’t see much beyond the densely packed shapes and seemingly random brush strokes, art enthusiasts will always appreciate the spontaneity and free expression of self that is naturally encompassed within Willem de Kooning’s creations.

Woman III by Willem de Kooning

Portrait of Adele Bloch-Bauer I

With quite a tumultuous history, Portrait of Adele Bloch-Bauer I is the first of two portraits by Gustav Klimt representing an art-loving lady from Vienna. Adele Bloch-Bauer and his wealthy husband were good friends and patrons of the artist, and Adele became the only model to be painted twice by Klimt.

About Gustav Klimt

One of the artists who initiated the Vienna Secession movement, Gustav Klimt was an Austrian symbolist painter who found most of his artistic inspiration in the female body. Many of his creations are marked by open eroticism, but Klimt also painted landscapes.

During his first period of success as an artist, he made remarkable architectural decorations, but his inclination to paint nudes attracted too much criticism. He consequently decided to no longer accept public commissions – a decision which eventually led him to the famous “golden phase”, or his second stage of artistic success.

Rather private, Klimt did not like to socialize with other artists very much, and he kept his interactions mostly limited to the Secession Movement and his undisclosed lovers. Patrons would have to visit him at home, where he passionately worked very long hours. He did not write much about himself and never made a self-portrait, saying “There is nothing special about me. I am a painter who paints day after day from morning to night… Whoever wants to know something about me… ought to look carefully at my pictures.”

This spectacular 54-inch by 54-inch oil and gold on canvas painting was commissioned by the model’s husband, industrialist Ferdinand Bloch-Bauer, and its completion took three years of work. After Adele’s death and the Nazi invasion of Austria, the masterpiece was confiscated together with the rest of the Bloch-Bauer properties. It was only in 2006 that it found its way back into the rightful heiress Maria Altmann’s hands, as established by a panel of judges.

Not long afterwards, the painting was sold for a remarkable $135 million through Christie’s. It now represents the most spectacular piece in businessman Ronald Lauder’s New York art collection. The rightful inheritors’ decision to sell all of the paintings that were restituted to them by the government was criticized by many. People expected the family to use this opportunity to tell a story of justice after the Holocaust instead of a tale of greed, as they see it.

Portrait of Adele Bloch-Bauer by Gustav Klimt

Portrait of Dr. Gachet

Vincent Van Gogh’s intention when painting his famous Portrait of Dr. Gachet was to immortalize the sensitivity, gentleness, intelligence and melancholy of the doctor who helped manage the artist’s health during the last months of his life. He described the project as a “modern portrait”, which was a fitting description for the then unconventional painting.

About Vincent Van Gogh

One of the most recognizable artists that ever lived, Vincent Van Gogh was a great post-impressionist painter, with a remarkable influence on the 20th century art. He drew landscapes, still lifes, portraits and quite a significant number of self-portraits. He was a remarkably prolific artist, producing over 2,100 artworks in only about one decade of activity: he started painting in his late twenties and he passed away at thirty-seven.

Even though he drew as a child, and even worked for an art dealing company, Van Gogh began his career as a painter only later. During his early adulthood, he was a very religious man, with a desire to become a minister, but his experience with religion turned out to be more frustrating than rewarding for him.

His brother Theo encouraged him to explore his artistic side and even connect with an important Dutch artist of the time, named Willem Roelofs. He took his new path very seriously and spent a lot of time studying and drawing. His first major work was finished in 1885, the same year that Van Gogh lost his father. After years of studying peasant characters, he finally created a truly remarkable piece, called The Potato Eaters.

Vincent Van Gogh’s life and artistic activity was tragically affected by mental illness. It was only towards the end of his life that he finally seemed to gain more confidence and control in his work. After moving to France in 1888 and discovering the French impressionists, he seemed to finally find his true personal style as an artist.
At the age of 37, however, he died as a result of an infection from a self-inflicted gunshot wound. After a short and intense life, Van Gogh left the world suddenly, but not without leaving a priceless artistic legacy behind.

Dr. Gachet was recommended to Van Gogh by a former patient of his, who knew of the doctor’s interest to work with artists. Upon meeting him for the first time, the painter felt disappointed by the doctor, describing him as “sicker than I am”. Soon afterwards, though, he found many similarities between them, both mentally and physically, and ended up being very fond of his caretaker.

In 1990, after changing hands a few times over the years, the first version of the portrait broke the record for the most expensive painting at the time, by fetching $82.5 million at a Christie’s auction. After the demise of his buyer six years later, the whereabouts of the painting remained undisclosed. To this date, the portrait remains the most expensive Van Gogh painting.

Portrait of Dr. Gachet by Vincent Van Gogh

Bal du Moulin de la Galette

Bal du Moulin de la Galette (popularly known as Dance at Le Moulin de la Galette) is one of the most notable masterpieces of the Impressionist era. It was painted in 1876 by Pierre-Auguste Renoir, who beautifully capture the atmosphere of the typical Sunday afternoon dance at Moulin de la Galette, in Paris.

About Pierre-Auguste Renoir

Contributing greatly to the development of the Impressionist movement, Pierre-Auguste Renoir was a French painter who loved and celebrated beauty, especially in the female figure. His talent for drawing was apparent from childhood, so when as a boy he worked in a porcelain factory, he was asked to decorate fine china.

He later went on to formally study art and meet a few important artists of the time, including Alfred Sisley and Claude Monet. While his success came slowly, Renoir did eventually become a highly regarded and very fashionable painter of his time. His work first received positive reactions at the Paris Salon of 1868, where Lise with a Parasol gained much attention.
The artist eventually became the co-founder of Impressionism, together with his friends Monet, Cezanne, Pissarro and Degas. The five of them decided to exhibit their paintings independently in 1874 in Paris, and that event became the world’s first Impressionist exhibition – which was actually not a very big success at the time.

Shedding the traditional styles and techniques, the artists created what people called “impressions”, rather than accurate and highly detailed representations of reality. Renoir loved working with brighter colors to create more luminous compositions, and he also enjoyed mixing various types of brushstrokes in order to best illustrate his visions. His three sons – Pierre, Jean, and Claude – inherited his artistic inclinations and went on to become an actor, a filmmaker, and a ceramic artist, respectively.

Working class Parisians of the time would gather there every week, all dressed up nicely and ready to dance, socialize, enjoy drinks and eat ‘galettes’ – a type of crusty cakes. Some of the characters in the painting were inspired by real people who regularly went to the dance, as the artist’s civil servant friend mentioned in his memoir called Renoir et ses amis.

There are two versions of the painting, both oil on canvas, but one is significantly smaller than the other. Experts could not determine which of the two was painted first, and other than their size, the differences between them are not significant: the composition is identical, and the colors are very similar, but the smaller painting flaunts a more fluid and spontaneous in execution.

The large version is safely displayed in the Musee d’Orsay, and has been since 1986. The smaller one, however, has been in private hands for many years. Its current owner has remained undisclosed, but the last public purchase happened in 1990, when the same collector who also bought the famous Portrait of Dr. Gachet by Van Gogh paid $78 million for it, making it the most expensive Renoir painting ever.

Bal du Moulin de la Galette by Pierre-Auguste Renoir

Richest Criminals & Gangsters and Their Troubling Stories

Probably one of the fastest ways to become rich is to engage in some sort of illegal activities. Now, while we do not approve their actions, we cannot exclude some of the world’s richest criminals from our luxury encyclopedia. They managed to build financial empires for themselves, enjoying luxury lifestyle services, vacations, properties, and everything in between.

Drug trafficking was the major source of income for most of these characters, but some also engaged in illegal weapon sales and terrorism. What is remarkable is the fact that some of them even made it into the famous Forbes lists of ridiculously rich people. In most cases their illegal operations and criminal actions led these leaders to prison and sometimes even death, but until that point hey all basked in an abundance of privileges and pretty much everything that money can buy.

Pablo Escobar

Pablo Emilio Escobar Gaviria the notorious Colombian drug lord

Pablo Escobar, aka The King of Cocaine, was a ridiculously rich Colombian drug lord, who dealt only with cocaine. He remained famous for his impressive wealth, being considered the world’s richest criminal ever. In the early 1990s, his drug empire translated to a personal fortune of about $30 billion ($58 billion after inflation adjustment for 2014). In 1989, Escobar’s cartel controlled 80% of the global cocaine market, which brought him worldwide notoriety. He was even featured on the Forbes list of billionaires, which included 227 people at the time.

The Story of Pablo Escobar

I’d rather be in a grave in Colombia than in prison in the United States

I can replace things, but I could never replace my wife and kids

Pablo Escobar and his soon Sebastián Marroquín( born Pablo Emilio Escobar )

Pablo Escobar wife Maria Victoria Henao

Pablo Escobar and his daughter Manuela Escobar Henao

As a child he set himself a very high goal: he wanted to become rich quick, and he had the ambition of being a millionaire by age twenty-two. Pablo (his full name was Pablo Emilio Escobar Gaviria) began his career as a criminal in his teenage years by selling contraband cigarettes, stealing cars, running petty street scams, selling fake lottery tickets, and even stealing and then selling gravestones. His brother later claimed that the gravestones were not stolen, but taken away from those who hadn’t paid for the site.

There can only be one king.

Pablo Escobar after his arrest for trafficking in 1976

In modern business it is not the crook who is to be feared most, it is the honest man who doesn’t know what he is doing.

The first time he made a quick $100,000 was in his early twenties, when he kidnaped and received a ransom for an important executive in Medellin, his hometown. Soon afterwards he entered the alluring realm of drug dealing and worked his way up to become its undisputed ruler in the city. The 1980s represented the height of his trafficking career, and at that time he would spend $1,000 a week on rubber bands that were used to wrap the innumerable stacks of cash.

The money was deposited mainly in warehouses, which led to a significantly high annual loss of ten percent, caused by rats that would creep in and nibble at the bills. Even so, Escobar’s wealth was increasing constantly, allowing him to enjoy a fabulous luxury lifestyle, while dealing with the authorities in a very simple way: his approach was called “plata o plomo”, which literally meant “silver or lead”, alluding to the fact that the authorities had only two options – to accept hefty bribes, or to be shot.

Having a native talent for public relations, the drug lord also played the Robin Hood card by helping the poor in his city. He would sponsor children’s football teams, and even help build schools, hospitals and churches. The poor loved him and voluntarily helped conceal his illegal operations by not talking to the authorities or by helping as lookouts. When he was finally cornered and shot dead by the police in 1993 at age 44, over 25,000 people attended his funeral.

Colombian police and military forces storm the rooftop where drug lord Pablo Escobar was shot dead

Pablo Escobar Grave

A good Tv Series about “El Patrón” is Narcos – ( A chronicled look at the criminal exploits of Colombian drug lord Pablo Emilio Escobar Gaviria )

Amado Carrillo Fuentes

Amado Carrillo Fuentes

For most people the phrase Personal Business Jet evokes fabulous leather interiors, executive designs with advanced built-in technologies, and even lavish en-suite bedrooms. For Amado Carrillo Fuentes, jets had a much more practical purpose: they had to transport tons of drugs in absolute safety to wherever his clients were. Hence his Senor de Los Cielos (Lord of the Skies) nickname.

If I die, nobody killed me. The only person who can kill Amado Carrillo is Amado Carrillo

Amado was one of the wealthiest criminals in the world, as well as one of the most powerful drug lords of his time. He was born in 1956 in a family that had experience in the drug business, so learning the trade was not difficult for him. He began his trafficking career under the guidance of his uncle, Don Neto, who was the leader of the Guadalajara Cartel.

He soon became Mexico’s top cocaine distributor, delivering four times more cocaine in the US than any other drug lord in the world. For that he had a serious fleet of Boeing 727 aircrafts (27 of them!) which he acquired with laundered money. He of course also had a few very comfortable luxury private jets for himself, which he used a lot for fleeing the country in search of safe havens.

He knew how to become rich in the world of illegal businesses, and during his lifetime he managed to amass a $25 billion personal fortune. Even though the authorities hunted him ever since he had assassinated and replaced the leader of the Juarez Cartel in 1993, seizing him was quite a challenge, as Amado proved to be one of the most sophisticated, diplomatic, powerful and low-key cartel leaders in Mexico.

As the search for him intensified, he decided to dramatically change his appearance by undergoing both liposuction and plastic surgery. In July 1997 he was admitted to the Santa Monica Hospital in Mexico City for the massive procedure, but the nine-hour operation proved fatal to him. Amado died on the operating table either due to a malfunctioning ventilator or because of the medication he received for the surgery. Some conspiracy theories were obviously also launched, but never proved.

Dawood Ibrahim

Criminals and wrongdoers who are highly successful in their enterprises are usually rich people. The more significant the damage they make, the wealthier they seem to be. Indian organized crime leader Dawood Ibrahim is one such character, enjoying a luxury life by creating mayhem in his country and in other places around the globe. He is currently one of the world’s most wanted people, ranking high on Interpol’s list of priorities.

Dawood is the head of an organized crime group called D-Company, which is unlike regular mafia organizations, given that its criminal actions also involve terrorist attacks and liaisons with dangerous groups such as Al-Qaeda. Back in 1993 Dawood was tied to the devastating Mumbai bombings, which led the Indian authorities to put him at the top of the list of India’s most wanted criminals. In 2003 it was proven that the crime lord had helped Al-Qaeda conduct their terrorist plans by allowing them to use his private smuggling routes.

He then became an official “global terrorist”, who operated not only against his own country, but against other nations as well. The United Nations decided to try and seize all of his assets from around the world, while also forbidding financial entities from working with him and his organization. A travel ban was also imposed among UN members.

Even though he is a widely known enemy of the Indian government, involved in large-scale illegal trafficking of narcotics and weapons, his family continues to lead a fairly public life in India. One of his daughters was married in 2005 to the son of a famous former Pakistani cricketer, and six years later his other daughter became the wife of a Pakistani-American. Despite his obvious relations to Pakistan, he claims he is not currently living in the Islamic country.

The Ochoa Vasquez Brothers

The Ochoa Vasquez Brothers

The three Ochoa Vasquez brothers – Jorge Luis, Juan David and Fabio – played a major role in founding the vicious Medellin Cartel in late 1970s’ Colombia. Juan David Ochoa, who was the oldest of the three, passed away in 2013 due to a heart attack. Before that, he had gone to prison for five years, only to be released in 1996 after a sentence plea bargain with the state.

Jorge Luis Ochoa, the middle brother, also spent time in prison and was released the same year as his brother after a five-and-a-half year sentence. They both had agreed to turn themselves in after former Colombian president Cesar Gaviria Trujillo offered reduced prison time in the country for drug traffickers like themselves. After years of extradition threats, the deal seemed very reasonable for the drug lords.

The youngest brother, however, did not enjoy the same treatment: Fabio Ochoa was extradited to the United States in 2001 and later sentenced to 30 years in a U.S. federal prison, where he still is today. Even after his brothers were released from penitentiary, Fabio continued his highly lucrative trafficking business, sending out regular shipments of cocaine in collaboration with the Milenio Cartel from Mexico. Between 1997 and 1999 he led massive smuggling actions of approximately 30 tons of cocaine per month.

The three were born in an entrepreneurial family, which started business legally. They owned family restaurant and cattle breeding businesses in the beginning, but that changed in the 1970s, when they found there were other ways to become rich, one of them being trafficking narcotics.

At least for a good few years, their decision allowed them to enjoy lavish lifestyles, owning expensive cars and relaxing onboard expensive yachts. In 1987 Juan David was ranked among the world’s twenty wealthiest people by Forbes, with a fortune of $3 billion. That, however, did not make the Ochoa family completely immune to the justice system, as history shows.

Khun Sa (Chang Chi-fu)

Khun Sa (Chang Chi-fu) – the Opium King (Source wikipedia)

Arm lord and drug trafficker Khun Sa was one of the wealthiest and most dangerous men in Burma. Also known as the Opium King, he built himself an illegal empire by producing, selling and distributing narcotics. After becoming rich, he started to call himself “Khun Sa”, which means “Prince Prosperus”. His actual name was Chang Chi-fu.

His mother was Shan, but his father was Chinese, so as a young man he trained with the Chinese Nationalist Party known as the Kuomintang. After the Chinese Civil War, however, he fled the party, organized his own small army, and started collaborating with the Burmese government, who provided his men with weapons, uniforms and money in return for fighting against the Shan rebels.

The army kept growing in numbers, so the leader decided to cease the collaboration and shift his focus towards the production of opium. His narcotics operations soon landed him to prison, where he spent four years, from 1969 to 1973. He was only set free because his second-in-command had kidnapped two Russian doctors and used them as leverage to obtain his leader’s freedom.

Shortly after his release, Khun Sa returned to his opium business and even started fighting the Burmese government for the autonomy of the Shan state. He continued to make smart alliances and gradually increase his power and success, eventually becoming one of the main leaders of the notorious Golden Triangle, one of the two main opium smuggling areas of Asia.

Khun Sa’s forces at Ner Mone Shan State 1990 (Source wikipedia)

By 1994, his operation had grown so much that it was providing 90% of the total heroin on the streets of New York. In the following years he offered to sell his entire crop of opium to both the Australian and the US governments, arguing that otherwise he would continue to sell it illegally as heroin. In 1996 he reportedly finally surrendered to the Burmese authorities to avoid being charged in the US.

Even though the US DEA had offered a $2 million reward for his arrest, the officials in Burma never imprisoned or extradited him. He lived in the country’s Rangoon area until his demise in 2007, at age 73. While the exact cause of death is unclear, it is known that he had suffered from a number of health issues, including high blood pressure, partial paralysis, and diabetes.

Khun Sa with Australian journalist Stephen Rice (Source wikipedia)

Jose Gonzalo Rodriguez Gacha

One of the main characters behind the notoriously dangerous Medellin Cartel in Colombia, Jose Gonzalo Rodriguez Gacha was also one of the richest criminals in the world. Forbes included his name in its 1988 list of world’s billionaires. While he did not become rich overnight, his involvement in illegal businesses led them there quite fast.

He was born in a small town to a poor family who did pig farming. He reportedly never continued his formal education beyond grade school, which was probably one of the reasons why he engaged into various criminal activities from a young age. He developed a reputation as a very dangerous young man when he became a hired killer for various groups. One of his most important early associations was with Veronica Rivera de Vargas, the first cocaine queen who had earned her status by murdering her competition.

In 1976 Rodriguez moved to Medellin, the place where he would eventually build his narcotics empire together with Pablo Escobar, the Ochoba family, and the rest of the Medellin Cartel leaders. Together they covered all the stages the cocaine business, from production to distribution and marketing. As he became increasingly better at his trade, the drug lord ventured into creating new trafficking routes into the US and Mexico. He was a great fan of the Mexican culture, which led people to call him El Mexicano (The Mexican).

Jose Gonzalo Rodriguez Gacha – EL MEXICANO

Rodriguez was also credited by his associates for being the first person to set up Tranquilandia – one of the most notorious and large jungle laboratories. Over two thousand people lived and worked there, producing, packaging and preparing cocaine for distribution. The success of his operations made the authorities increasingly anxious and determined to disrupt the cartel’s illegal activities. They eventually even agreed to extradite Colombian citizens, putting the all the narcotraffickers at the top of the list.

The government’s anti-drug actions led to an outright war between the justice system and the Medellin Cartel, who went so far as to create its own paramilitary organization. Hundreds of judges, politicians and even civilians were killed in a number of terrorist actions led by the cartel. Bombings and assassinations happened almost daily for several months in 1988.

Rodriguez was eventually coughed by the police in December 1989, when his son unsuspectingly led them to his father’s hiding place. The kingpin committed suicide by detonating a grenade, and a surprisingly large number of people came to his ensuing funeral: it was estimated that approximately 15,000 mourners gathered around the cemetery.

Gilberto and Miguel Rodriguez Orejuela

Gilberto Jose Rodriguez Orejuela together with his brother Miguel Angel Rodriguez Orejuela and Jose Santacruz Londono were the heads of the Cali Cartel which they founded in Colombia during the 1970s. They started building their drug trafficking empire with marijuana, but during the 1980s they branched out and included cocaine in the business.

The cartel soon became the main supplier of cocaine for both the US (an estimated 80%) and Europe (90%), which obviously translated to huge personal fortunes for the brothers. Unlike their rivals in the extremely violent Medellin Cartel, the leaders of the Cali Cartel were more inclined to avoid the legal consequences to their illegal actions by bribery and not assassinations.

Gilberto and Miguel Rodriguez Orejuela (Source)

That determined the authorities to keep pretty much all their attention on the rivaling drug lords in Medellin, who in turn responded with even more violence and also acts of terror. While the state was engaged in an outright war with the other crime bosses, the Rodriguez Orejuela brothers and their associates continued to focus their energies in laundering money and smuggling drugs across the borders, which resulted in a period of visible growth for their organization.

After the Medellin Cartel was dismantled by the authorities in the early 1990s, the police switched focus towards the traffickers in Cali. In 1995 both Gilberto and Miguel were captured and sentenced to prison. They started their prison life in Colombia, but several years later they were both extradited to the United States, where they were accused of both trafficking and money laundering, which resulted in 30-year sentences for each of them. They are currently detained in different federal institutions.

Carlos Enrique Lehder Rivas

Like most crime lords, Carlos Lehder began his illegal activities young. He was born into a mixed-nationality family (German father and Colombian mother) who operated a semi-legal used car business. He contributed to the family business by stealing American vehicles and bringing them home for sale. He also engaged in marijuana dealing on the side, but was eventually arrested and imprisoned in Danbury, Connecticut for car theft.

Carlos Lehder – Drug Dealer, Organized Crime(Source)

It was during his time in prison that he met his future business partner Geroge Jung, who had experience in smuggling marijuana using a small aircraft. Jung’s stories seemed fascinating to Lehder, who decided that once he would be released he would try to take advantage of the blooming cocaine market of the time. He invited Jung to join his plans and then kept learning everything he could about drug trafficking and money laundering from his fellow inmates.

After Lehder and Jung were released from prison, they used two American women to smuggle cocaine in their suitcases after a paid vacation in Antigua. After repeating this classic trafficking process for several times, they raised enough money to purchase a small plane and pay a professional pilot to help them fly large amounts of cocaine into the US via the Bahamas. The plane would always stay below radar and then land on dry lakebeds, which was an innovative way of trafficking narcotics at the time.

The business soon flourished and Lehder could afford to bribe enough Bahamas officials to make sure that he could continue his operations unhindered. He also gained increasing credibility among other drug lords, which opened new doors and opportunities for him. His success gradually turned him into a megalomaniac with a ridiculously luxurious lifestyle and even plans to own his very own Bahamian island with the purpose of setting his business headquarters there.

The island that he chose was Norman’s Cay, which at the time held only about 100 private properties. Lehder made sure every inhabitant felt threatened to the point where they would move away and leave the island to him. He also forced Jung out of the business and kept working with the Medellin Cartel to bring tons of cocaine into the US every year. Between 1978 and 1982 his island was the main drug smuggling hub in the Caribbean, and also a place where he and his associates could bask in luxury.

In 1984 Colombia announced that it would extradite its drug traffickers to the United States, which marked the beginning of the fall for Carlos Lehder and his associates. The government also froze all of his accounts, suddenly sending him into near bankruptcy. He was forced to retreat in the jungle, where he became very ill and had to be flown into Colombia by Escobar in order to receive medical attention. There he was later betrayed and handed over to the authorities, which in turn sent him into the US, where he is still imprisoned today.

Griselda Blanco

Griselda Blanco was a notoriously violent cocaine trafficker and an important figure in the Medellin Cartel. Also known as the Black Widow, the Cocaine Godmother, the Queen of Narco-Trafficking, La Madrina, or La Dama de la Mafia (The Lady of the Mafia), she had a pioneering role in the Miami cocaine trade during the 1970 and early 1980s.

Griselda Blanco – The Lady of the Mafia

Blanco and her mother moved from their home place in Cartagena, Colombia to Medellin when she was only three years old. With a reportedly abusive mother and living in a slum neighborhood with bad company, she quickly became involved in criminal activities. She was only eleven years old when she reportedly kidnapped and tried to ransom a child from an upscale neighborhood, but ended up shooting and killing the boy.

At age 14 she decided to run away from home, and later got engaged in prostitution. After years of pickpocketing and other petty crimes, she eventually started doing major hustles together with smuggler Carlos Trujillo, who later became her husband and the father of their three children. The relationship ended a few years later and it is believed that Griselda had him murdered after a drug-related argument.

In the mid-1970s she and her second husband moved to New York, where they established a flourishing cocaine operation which spanned across the entire United States. At the peak of her business she was making over $80 million per month, which allowed her to indulge in a highly luxurious lifestyle. Her inclination for violence, though, attracted a lot of attention from the authorities, who charged her and thirty subordinates of hers on federal drug conspiracy charges. This was the largest cocaine case in history at the time.

Griselda Blanco was a notoriously violent cocaine trafficker and an important figure in the Medellin Cartel

To avoid the US authorities, Blanco fled to Colombia only to return to Miami a few years later. The DEA finally arrested her in 1985 and she was condemned to over ten years of prison time. Later she was indicted of three murders, but due to some technicalities she had to be released and deported to Colombia in 2004. Having had an extremely violent business approach (even murdering her cocaine suppliers to avoid payment), she soon found herself surrounded by enemies who all wanted her dead. In 2012 she was murdered in a drive-by shooting in Medellin.

Al Capone

Al Capone, the infamous Italian leader of Chicago organized crime

Few criminals are as widely known as Al Capone, the infamous Italian leader of Chicago organized crime. Born into a family of immigrants, he was not the stereotypical poor foreign kid, but the son of a respectable family. Even though he did pretty well in school, he decided to quit formal education at age 14 after he hit a teacher in the face and got expelled for it. He took various jobs after that, but felt that he learned the most from Johnny Torrio, a gangster whom he saw as a mentor.

The legendary gangster Al Capone (Source)

Torrio taught him how to be a racketeer and yet keep an appearance of integrity, and Capone was quick to learn everything that the mafia business required. His famous “Scarface” nickname was given to him after he got into a fight with a young man in a club for unintentionally insulting his sister. The man slashed his left cheek with a knife, and Capone was stuck with a moniker that he loathed. His friends called him “Snorky”, which was slang for well-dressed and elegant.

Al ‘Scarface’ Capone, nickname he received because of the scar on his face, caused by a cutting knife

I don’t even know what street Canada is on.

At age 20 the young gangster was summoned to Chicago by Torrio and it is alleged that he also assassinated his mentor’s boss in order to help make him the new boss of the successful brothel where they were working. Torrio retired in 1925 after having shot several times in an assassination attempt and decided to leave Capone in charge of their operations. By this time they had already built a small mafia empire that revolved around bootlegging, gambling, prostitution and extortion. He was making around $100 million a year, and he didn’t mind drawing the media’s attention with his luxurious cars and expensive jewelry.

Al Capone’s bullet proof car (Source)

The Kursaal’s re-enactments of Al Capone’s shoot-outs

He became increasingly preoccupied with safety and protection, travelling everywhere with bodyguards, but never actually carrying a gun. He did that as a symbol of status and power. After his father’s unexpected demise, he altogether stopped trying to keep a respectable façade and lived a blatantly lawless lifestyle. He murdered at least four people himself, and had countless others killed by his subordinates. By paying off the city’s authorities, he also enjoyed plenty of protection from the justice system while conducting his immensely lucrative alcohol business in a time of prohibition.

Al Capone a celebrity. Ringside at Comiskey Park, sitting with state Rep Roland Libonati(Source)

The one act that made him lose much of his power and respect in the public eye and among officials was the infamous Saint Valentine’s Day Massacre. The event happened in 1929, when Capone was trying to eliminate his long-time rival Bugs Moran and his North Siders gang. The men were lured into a garage where they were told they would be sold whiskey, but then few of Al Capone’s people git dressed in fake police uniforms and pretended to raid the place. They lined the victims along a wall and executed them with machine guns. Seven men were killed in the massacre, and the event became national media news.

Al Capone’s police mug shot

May 1932, Al Capone was transferred to prison for tax evasion(Source)

Now I know why tigers eat their young.

While no one could directly link the assassinations to Capone, the police knew exactly who had been behind them. Actually, the mafia head never went to prison for any of his murders. It was only tax evasion that the authorities could eventually link him to, and so in 1931 he was sentenced to eleven years of prison time. By this time his health was increasingly poorer due to his syphilis complications. After he started to manifest dementia symptoms, the court reduced his sentence and released him. He died at home, surrounded by his family, after suffering a heart attack in 1947.

Al Capone’s death certificate

When I sell liquor, it’s called bootlegging; when my patrons serve it on Lake Shore Drive, it’s called hospitality.