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Fidel Castro holds a cigar during a news conference in Havana in 1961. The hand-rolled cigar held a certain cachet during the 1990s in the United States, the number of American smokers has declined. Castro died at age 90 on Nov. 25, 2016.The Associated Press

Fidel Castro's first attempt at revolution in Cuba was an utter failure. Some of his followers got lost on the way to the Moncada barracks in the city of Santiago. One car blew a tire. Surprised by an army patrol, the rebels botched their assault. A few were killed on the spot; dozens were hunted down, tortured and killed by dictator Fulgencio Batista's troops. The rest surrendered or, like Mr. Castro, were captured over the next few days.

Yet, so powerful was Mr. Castro's appeal to alienated and impoverished Cubans that he managed to turn the 1953 Moncada affair into a victory. From the prisoner's dock, at the end of his trial on insurrection charges, he delivered a resounding call to freedom, denouncing General Batista's oppressive ways and ending defiantly: "Condemn me, it does not matter. History will absolve me!"

Mr. Castro died on Friday, at the age of 90, his younger brother and successor, Raul Castro, announced on state television.

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History is famously fickle, and not always that generous. Today, Mr. Castro is reviled as well as revered. But the speech was a psychological coup d'état, laying the groundwork for the guerrilla triumph that drove Gen. Batista into exile less than six years later. And long before Mr. Castro's death, the history of the 20th century bore his indelible stamp. It was the mark of a born leader and opportunist – a man whose sense of the transformative moment and talent for turning adversity into advantage were rarely matched.

With his signature forage cap, beard and cigar, Mr. Castro became an icon for a world weary of big-power politics and domination by the rich. He made Cuba a beacon for have-not nations, with quality free health care and education. He inspired a generation of young Latin Americans to confront inequality and repression. As bugs to a bonfire, a certain class of international celebrity fluttered to his side.

Yet by the time he died, Mr. Castro's revolution had been drained of its vitality and its many unsavoury aspects were exposed to full view. His opponents languished in prison. Political activity outside the Communist Party was not tolerated and access to information was strictly controlled.

The fervour of the 1960s and the Soviet-backed prosperity of later decades were distant memories. Mr. Castro dealt with economic hardship by tightening his grip. Thousands fled the impoverished island; others resigned themselves to hanging on until Fidel was gone.

Mr. Castro watched 10 U.S. presidents and six Russian leaders leave office. When he seized power on Jan. 1, 1959, John Diefenbaker was Canada's prime minister and Justin Trudeau was not yet born.

He owed his durability to many factors: a prodigious memory, a compulsion for self-challenge, the ability to think several moves ahead. He was famously restless – sleeping little, moving from residence to residence, convening midnight dinner parties on a whim. He would lecture anyone on anything, or so it seemed. His biographer, Tad Szulc, wrote of a hostess who chided Mr. Castro for telling her maid how to cook plantains. "Do you think you know everything?" she asked. "Almost everything," the commander-in-chief replied.

Few were able to penetrate his emotional armour, although Mr. Szulc records a rare moment of introspection in which he confessed: "I detest loneliness." Noting Aristotle's comment that man was a social being, he remarked: "It seems I belong to that species."

As it turned out, Pierre Trudeau was just such another specimen. As prime minister, Mr. Trudeau paid an official visit to Cuba in 1976 and began a friendship that characterized Canada's relationship with the island. Mr. Trudeau returned several times after leaving office. "I rarely saw him listen to somebody like he listened to Pierre Trudeau," Mark Entwistle, the former Canadian ambassador to Cuba, told The Canadian Press. "He'd actually be silent for extended periods."

By all accounts, Mr. Trudeau made a lasting impression. In 2000, Mr. Castro attended his funeral in Montreal.

When Mr. Castro was born, Cuba had been a sovereign country for just 24 years. Its struggle for independence had left the country devastated and under heavy U.S. influence. Americans were rapidly establishing businesses and buying up huge sugar plantations. Meanwhile, thousands of rural workers remained in desperate poverty.

His Spanish-born father arrived in Cuba penniless but came to own a sizable farm. His mother worked in the household as a maid, and eventually became his father's second wife.

Mr. Castro enjoyed the outdoors and excelled at sports, particularly basketball. But a cantankerous streak soon emerged. According to Mr. Szulc, he was insolent at school and, on occasion, forged report cards. As a teenager, working summers on the family farm, he tried to persuade his father's employees to form a union. He was a landowner's son, but his friends were the children of peasants, and he later said the injustice he witnessed influenced him profoundly.

He moved to Havana to study at a Jesuit college and later at the University of Havana law school. The university was heavily politicized, divided into armed factions and, as he became involved in student politics, Mr. Castro began carrying a gun for protection. His fiercest opponents say he was a Communist from the get-go. But the best evidence indicates that he started out as a nationalist heavily influenced by Cuban independence hero Jose Marti.

In 1948, Mr. Castro was attending a student congress in Bogota when fierce rioting broke out after the assassination of a popular politician. "I see there is a revolution erupting," he later told an interviewer, "and I decide to be part of it." He got himself a gun, fashioned a uniform, exhorted soldiers to join the revolution and gave tactical advice to sympathetic police.

The revolt ended in a truce, but not before Mr. Castro had drawn some lessons. A revolution, he concluded, must be the product of education, planning and discipline – not an exercise in anarchy. "The greatest influence was in the Cuban revolutionary strategy, in the idea of educating the people during our struggle," he told another interviewer.

Back in Cuba, Mr. Castro graduated from university, opened a law practice and became an election candidate for the opposition Orthodox Party. But the voting was cancelled after Gen. Batista seized power in a coup, and Mr. Castro began plotting his abortive uprising. He spent 17 months in jail after the Moncada trial, then flew to Mexico, where he began military training with a group of followers – including a young Argentine doctor named Ernesto (Che) Guevara.

Late in 1956, Mr. Castro and several dozen guerrillas arrived on Cuba's southeastern coast and headed into the Sierra Maestra mountains. They were badly outmanned and outgunned, but had strong support from local peasants, and the knowledge that Mr. Castro had returned to Cuba emboldened sympathizers throughout the island. Soon the rebels were scoring successes. Their propaganda campaign included the engineering of a clandestine New York Times interview that introduced Mr. Castro to the rest of the world.

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It was in the Sierra Maestra that Mr. Castro began growing his beard, and where he met Celia Sanchez, who remained a close companion for many years. He had already married Mirta Diaz-Balart, a fellow student who bore his first son, Fidelito, in 1949, but for Mr. Castro, the revolution far outstripped family life as a priority. They divorced in 1955 and Ms. Diaz-Balart eventually left Cuba to live in Spain.

By mid-1958, the Batista regime was in panic mode. An air and ground campaign failed to crush the rebels. In October, Mr. Castro launched his own offensive. Early on New Year's Day, 1959, Gen. Batista flew into exile, and more than four decades of revolutionary rule began.

Cubans hailed the rebels as liberating heroes, and Mr. Castro moved swiftly to reshape Cuba. By the end of 1960, large-scale nationalization and land reform programs had begun. A literacy campaign and the frank espousal of Marxism-Leninism soon followed.

Mr. Castro personally directed the rout of the U.S.-backed invasion at the Bay of Pigs. Amid Washington's hostility, he turned steadily toward Moscow for support, and the world came to the brink of nuclear war in 1962 after the installation of Soviet missiles began on the island.

Communist Party control over the government and economy grew steadily during the 1960s, and in 1976, Mr. Castro was elevated from the post of prime minister to the presidency. Those who looked as if they might pose a challenge were relegated to obscurity or prison, and on occasion – as with four army officers allegedly implicated in drug trafficking – were executed.

In 1980, Mr. Castro jousted skillfully with Washington, creating a refugee headache by allowing more than 120,000 disaffected Cubans to set sail for Florida. He dismissed the taunts of Cuban-American exiles with contempt, and sent Cuban troops to Angola.

Writing in the mid-1980s, Mr. Szulc described activities at Cayo Piedra, Mr. Castro's island retreat. He would arrive by helicopter and spend the day offshore in a wetsuit, spear-fishing for lobster and red snapper. After cocktails, the catch would be served for dinner following a first course of turtle soup. Mr. Castro gave up cigars in 1985, saying it was a necessary sacrifice for the promotion of public health. He was not a great drinker, but enjoyed Scotch. In private, Mr. Szulc writes, his speech was often laced with profanity. In public, he took care to express himself in polished Spanish – often in speeches lasting several hours.

His closest ally was his younger brother Raul – his designated successor and head of the armed forces. But he draped a shroud over his personal life. Until recently, he allowed no public profile to Dalia Soto del Valle, the former schoolteacher with whom he began a relationship in the 1960s (and may have legally married) or their five sons. His daughter Alina, born in the 1950s of an affair with a well-to-do Havana woman, lives in Miami and is an outspoken critic. In the early 1990s, Mr. Castro faced a dramatic challenge with the collapse of the Soviet Union. Without Moscow's economic concessions, Cuba hurtled toward destitution. Mr. Castro reacted by instituting emergency measures, adopting the U.S. dollar as currency and aggressively courting foreign investment in tourism. Mr. Castro was dismayed by the explosion in small-scale entrepreneurship, including prostitution, but opted to curb rather than crush it.

He had no such compunction about cracking down on political dissidents and independent journalists. World leaders who tried to persuade him to ease up were rebuffed. In April, 1998, at the end of prime minister Jean Chrétien's official visit to Havana, I stood on the airport tarmac with a clutch of journalists, my chin about six inches from Mr. Castro's beard, and asked him why Cuba would not release the four political prisoners whose cases Mr. Chrétien had taken up.

In reply, he cited the trade embargo maintained against Cuba by the United States since 1962. "That's the No. 1 thing that's important to us," he said. "No one has the right to ask anything or expect anything from us on behalf of the United States while they maintain an embargo." It was a clear indication of how Cuba's tortured relations with Washington shaped his decision-making, and how little leverage other governments had in Havana.

To make up for the lost Soviet backing, Mr. Castro sought support throughout the Americas. In then Venezuelan president Hugo Chavez, he found a new ally and a source of relatively cheap oil. In 2000, he scored another victory against his exile opponents by securing the return of six-year-old Elian Gonzalez, a shipwreck victim who had washed up alive on the Florida coast. Such triumphs notwithstanding, Mr. Castro's physical strength began to fail. In 2001, he fainted briefly during a speech; in 2004, he shattered his kneecap and broke his arm in a fall. He signalled something more serious in July, 2006, taking the unprecedented step of handing power to his brother Raul before undergoing a series of operations.

When the subject of his death came up, Mr. Castro liked to play down its significance. "To suppose that the death of one individual could liquidate the work of a people … is really ridiculous," he said in a 1998 speech. It has been so long since anyone else set the agenda in Cuba that it is hard to know whether that remark will prove true.

Fidel Alejandro Castro Ruz was born at Finca Manacas near Biran, Cuba, on Aug. 13, 1926. He died on Nov. 25, 2016, at the age of 90. He leaves his partner, Dalia Soto del Valle, and seven children.