It took a rather liberal interpretation of the term "world leaders" but it should technically fulfill the original poster's criteria. The interesting thing in this challenge, at least for me was to make being a bank robber or hobo, an integral part of their personality. I hope I succeed and you like my little timeline.
The Rise of Illegalist Anarchism
or the Fourth International
The Napoleon of Crime (The Bank Robber)
Illegalism first rose to prominence among a generation of Europeans inspired by the unrest of the 1890s, during which Ravachol, Émile Henry, Auguste Vaillant, and Caserio committed daring crimes in the name of anarchism, in what is known as propaganda of the deed. Influenced by theorist Max Stirner's egoism, described in his The Ego and Its Own
. The illegalists in France broke from anarchists like Clément Duval and Marius Jacob who justified theft with a theory of la reprise individuelle (Eng: individual reclamation). Instead, the illegalists argued that their actions required no moral basis - illegal acts were taken not in the name of a higher ideal, but in pursuit of one's own desires. "In Paris, this milieu was centered on the weekly paper, L’Anarchie and the Causeries Populaires (regular discussion groups meeting in several different locations in and around the capital each week), both of which were founded by Albert Libertad and his associates"
The most famous Bonnot Gang (La Bande à Bonnot) was a French criminal anarchist group that operated in France and Belgium during the Belle Époque, from 1911 to 1912. Composed of individuals who identified with the emerging illegalist milieu, the gang utilized cutting-edge technology (including automobiles and repeating rifles) not yet available to the French police. Illegalism as a practice emerged and within it "The acts of the anarchist bombers and assassins ("propaganda by the deed") and the anarchist burglars ("individual reappropriation") expressed their desperation and their personal, violent rejection of an intolerable society. Moreover, they were clearly meant to be exemplary , invitations to revolt.". But in another less dramatic sense "At that time this term was used to indicate all those practices prohibited by law that were useful for resolving the economic problems of comrades: robbery, theft, smuggling, counterfeiting money and so on." Such acts of rebellion which could be individual were in the long run seen as acts of rebellion which could ignite a mass insurrection leading to revolution.
Bonnot Gang
While the movement lacked a explicit leader, being a Union of Egos, of Individuals, one of the had the biggest Ego and the sharpest mind. Jules Bonnot was born in October 14, 1876 and died in April 28, 1912) He viewed himself as a professional and avoided bloodshed, preferring to outwit his targets. Often posing as a businessman, his taste in expensive clothing earned him the pseudonym "Le Bourgeois" among comrades.
Although Bonnot was never the official leader of the group, the gang was dubbed the "Bonnot Gang" by the press after Bonnot appeared, armed with a Browning automatic, in the office of the Le Petit Parisien to file a complaint about the daily paper's coverage of the group. Bonnot was quoted as having stated, "We'll burn off our last round against the cops, and if they don't care to come, we'll certainly know how to find them."
On April 24, three policemen surprised Bonnot in the apartment of a suspected fence. He shot at the officers, killing Louis Jouin, the vice-chief of the French police (Sûreté Nationale), and wounding another officer before fleeing over the rooftops. Part of the 100,000 franc reward was later given to the widow of Jouin. On April 28, police tracked Bonnot (now France's "most wanted" criminal) to a house in the Paris suburb of Choisy-le-Roi. They besieged the residence with 500 armed police officers, soldiers, firemen, military engineers and a lynch mob of local citizens. Armed with three Brownings and a Bayard pistol, Bonnot succeeded in wounding three police officers.
By noon, after sporadic firing failed to extract Bonnot from the house, Paris Police Chief Louis Lépine ordered the building bombed, using a dynamite charge. The explosion demolished the front of the building. Barely conscious, lying underneath a mattress, Bonnot was shot ten times in the upper-body before Lépine shot him non-fatally in the head. Afterwards police had to prevent the spectators from lynching Bonnot. They simply told the crowd that Bonnot was already dead and had been buried in a secret grave.
Jules Boonot
The police didn't notice that they were followed by the Russian Bolshivik Kamo who after feigning insanity for more than three years, had escaped from the psychiatric ward of the Tiflis prison by sawing through his window bars and climbing down a homemade rope. Kamo was Lenin's specialist for "extradicitons" (he planned the Tiflis bank robbery for example). He recently met up with Lenin in Paris to discuss their next activities. There he heard of Bonnets activities and decided that he wanted to meet the man.
Instead of simply meeting him, he freed Bonnet by pretending to be doctor. Bonnet who was moved to the Hotel-Dieu and pronounced dead at 1:15 PM by Kamo. Wounded to an insane degree under the care of Kamo and some of his contacts Bonnet recovered. The exact details of what happened later are unknown but somehow Bonnet managed to become the head of a anarchist criminal syndicate. Known as the "true" Napoleon of Crime the paralyzed Bonnet became a feared world leader of an international syndicate, willing to bring down the worlds government and bourgeoisie.
The Tramp (Hobo)
Charles Spencer “The Tramp” Chaplin was born on 16 April 1889 to Hannah Chaplin and Charles Chaplin Sr.. There is no official record of his birth, although Chaplin believed he was born at East Street, Walworth, in South London. His mother and father had married four years previously, at which time Chaplin Sr. became the legal carer of Hannah's illegitimate son, Sydney John . At the time of his birth, Chaplin's parents were both entertainers in the music hall tradition: Hannah, the daughter of a shoemaker, had a brief and unsuccessful career under the stage name Lily Harley, while Charles Sr., a butcher's son,worked as a popular singer.The Chaplins became estranged in around 1891; a year later, Hannah gave birth to a third son—George Wheeler Dryden—fathered by music hall entertainer Leo Dryden. The child was taken by Dryden at six months old.
Chaplin's childhood was beleaguered by poverty and hardship, prompting biographer David Robinson to describe his eventual trajectory as "the most dramatic of all the rags to riches stories ever told." His early years were spent with his mother and brother in the London district of Kennington; Hannah had no means of income, other than occasional nursing and dressmaking, and Chaplin Sr. provided no support for his sons. Because of this poverty, Chaplin was sent to a workhouse at seven years old. The council housed him at the Central London District School for paupers, which Chaplin remembered as "a forlorn existence". He was briefly reunited with his mother at nine years old, before Hannah was forced to readmit her family to the workhouse in July 1898. The boys were promptly sent to Norwood Schools, another charity institution.
Charles Chaplin before his accident
In September 1898, Hannah Chaplin was committed to Cane Hill mental asylum—she had developed a psychosis seemingly brought on by malnutrition and an infection of syphilis. Chaplin recalled his anguish at the news: "Why had she done this? Mother, so light-hearted and gay, how could she go insane?" For the two months she was there, Chaplin and his brother were sent to live with their father, whom the young boy scarcely knew.Charles Chaplin Sr. was by then a severe alcoholic, and life with the man was bad enough to provoke a visit from the National Society for the Prevention of Cruelty to Children.
He died two years later, at 37 years old, from cirrhosis of the liver. Hannah Chaplin entered a period of remission, but in May 1903 became ill again. Chaplin, then 14, had the task of taking his mother to the infirmary. He lived alone for several days, searching for food and occasionally sleeping rough, until his brother Sydney returned from the navy. Hannah Chaplin was released from the asylum eight months later, but in March 1905 her madness returned, this time permanently. "There was nothing we could do but accept poor mother's fate", Chaplin later wrote, and she remained in care until her death in 1928.
Young performer
Chaplin's first stage appearance came at five years old, when he took over from his mother one night in Aldershot. Hannah had been booed off stage, and the manager chose Chaplin, who was standing in the wings, to go on as her replacement. The young boy confidently entertained the crowd, and received laughter and applause. It was an isolated performance, but at nine years old Chaplin became interested in the theatre. He credited his mother, later writing "[she] imbued me with the feeling that I had some sort of talent." Through his father's connections, Chaplin became a member of The Eight Lancashire Lads clog dancing troupe. He began his professional career in this way, as the group toured English music halls throughout 1899 and 1900. Chaplin worked hard and the act was popular with audiences, but dancing did not satisfy the child and he dreamt of forming a comedy act.
By age 13 Chaplin had fully abandoned education. He supported himself with a range of jobs, but said he "never lost sight of my ultimate aim to become an actor." At 14, shortly after his mother's relapse, he registered with a theatrical agency in London's West End. The manager sensed potential in Chaplin and he was soon on the stage.His first role was a newsboy in H. A. Saintsbury's Jim, a Romance of Cockayne. It opened in July 1903 in Kingston upon Thames, but the show was unsuccessful and it closed after two weeks. Chaplin's comic performance, however, was singled out for praise in many of the reviews. From October 1903 to June 1904, Chaplin toured with Saintsbury in Charles Frohman's production of Sherlock Holmes. He repeated his performance of Billy the pageboy for two subsequent tours, and was so successful that he was called to London to play the role alongside William Gillette, the original Holmes."It was like tidings from heaven", Chaplin recalled. Chaplin starred in the West End production at the Duke of York's Theatre from 17 October to 2 December 1905. He completed one final tour of Sherlock Holmes in early 1906, eventually leaving the play after more than two and a half years.
Vaudeville star
Chaplin quickly began work in another role, touring with his brother—who was also pursuing an acting career—in a comedy sketch called Repairs. He left the troupe in May 1906, and joined the vaudeville act Casey's Court Circus. Chaplin's specialism with the company was a burlesque of Dick Turpin and the music hall star "Dr. Bodie". It was popular with audiences and Chaplin became the star of the show. When they finished touring in July 1907, the 18 year old was an accomplished comedian. Several months of unemployment followed, however, and Chaplin lived a solitary existence while lodging with a family in Kennington. He attempted to develop a solo comedy act, but his Jewish impersonation was poorly received and he performed it only once.
By 1908, Sydney Chaplin had become a star of Fred Karno's prestigious comedy company. In February, he managed to secure a two-week trial for his younger brother. Karno was initially wary, thinking Chaplin a "pale, puny, sullen-looking youngster" who "looked much too shy to do any good in the theater." But the teenager made an impact on his first night at the London Coliseum, winning more laughs in his small role than the star, and he was quickly signed to a contract. His salary was £3 10s a week. Chaplin's most successful role with the Karno company was a drunk called the Inebriate Swell, a character recognized by Robinson as "very Chaplinesque". He took it to Paris in the autumn of 1909.
There Chaplin's life would change forever. Caught up in the explosion of a steam boiler his face got severely burned. While Chaplin mostly recovered, still able to act as a pantomime, his scarred face.
After almost succeeding, having tasted how sweet life could be, his world crashed down and burned. Like his mother he was brought into an insane asylum like his mother. Nicknamed "scarface", by the wards and some of the inmates he would spend the next four years trying to get back into life. After his release he was a sane but broken man. Living as homeless man, he earned himself some money by performing comedy routines that didn't rely on facial expression, wearing bandaged to hide his face. As many other homeless and other desperately poor people he earned himself some money by working for the people's syndicate, the name Bonnet had given his new organization. Impressed by the accuracy of his information, despite all the suffering, despite living on the street, Chaplin never lost his perfectionist streak, he was recruited for higher missions. In the next decades Chaplin rose in the organization until he became the new head of the syndicate. Unlike Bonnet Chaplin never bought any expensive closes, in fact he always kept his ragged old clothes, earning him the nickname "Tramp". The other obvious option "Scarface" was lethally discouraged.
How could the people's syndicate become so powerful?
This question is not easy to answer, many factor played a role. The Pyrrhic victory of the "white" forces in the Russian Civil War, leading to Warlordism. The same happening in China, which was later devastated by Japanese Invaders that, where however unable to enforce any stability themselves. The assassination of the hopeful American presidential candidate Roosevelt certainly played a role, as well as the Great Depression, that devastated the US society and strengthened the isolationist movement. The inability of Weimar to restore order, while still being able to prevent any strong leader to rise to power and clean up the rotten Republic. The almost civil war in France between the socialist and the conservative, vying for power, threatening another French revolution, the collapse of the British Empire after India was engulfed in the flames of violent revolt. A world filled with insecure governments, barely able to assert authority, a dead League of Nations that isn't able to bring the promised peace, not even for a little while and a seemingly never ending downward spiral of inflation and economic of constant booms and busts. In a world lacking any social safety networks, any hope of recovery, who wouldn't turn to the only organization promising help and solidarity, the People's (Crime) Syndicate, the "Fourth International".
