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For 14 years, he was the Western Hemisphere’s most polarizing head of state. Generous while heavy-handed, charming but cold-blooded, Hugo Chávez Frías was adored by Venezuela’s proletariat while loathed by free market capitalists, center-right political rivals and many in the United States, who viewed the boisterous leader as the second coming of Fidel Castro.

Chávez, 58, died Tuesday after succumbing to cancer, a disease which he had battled since 2011 and which kept him out of his country for much of the last two years. The enigmatic former leader of the Bolivarian Republic of Venezuela leaves behind both a legacy that transformed relations between Latin America and Western powers as well as a number of doubts about the direction his country – and Latin America as a whole – will go in a post-Chávez world.

“Throughout Latin America his influence was very profound,” said Larry Birns, the director of the Council of Hemispheric Affairs. “He had a vision and that vision was his version of socialism in the 21st century.”

The former Venezuelan leader’s rise from humble communication officer in the country’s army to the 21st century face of Latin American socialism began with an aging, bullet-riddled Mercedes-Benz.

You either love him of hate him...He's become a national obsession.

— Chris Sabatini, the senior policy director at the Americas Society/Council of the Americas

The car belonged to an all-but-defeated Marxist-Leninist guerrilla group in Chávez’s home state of Bariñas. Prying the trunk of the car open, the young Chávez found a stash of books: Marx, Lenin, Mao and “The Life and Times of Ezequiel Zamora” – a book by a Venezuelan Federalist soldier who was one of Chávez’s childhood heroes.

These books, along with his undying devotion to South American liberator Simón Bolívar, helped shape Chávez’s nascent political views and deepened his commitment to the left.

“By the time I was 21 or 22, I made myself a man of the left,” Chávez said later, according to Bart Jones, a former Associated Press reporter who authored biography on the Venezuelan leader.

Chávez continued to foster his political ideology as he rose through the ranks of the Venezuelan military, indoctrinating younger soldiers with his “Bolivarian" teachings and building up a network of colleagues who would go on to form a secret cell in the army called the Revolutionary Bolivarian Movement-200 (MBR-200).

In 1992, Chávez simultaneously suffered his greatest defeat and his public arrival on the national stage.

Operation Zamora, a failed coup attempt against the corrupt President Carlos Andrés Pérez, landed Chávez both in prison and in the headlines. His legend as a defender of the country’s poor was cemented.

Upon his release from the stockade, Chávez’s political prominence continued to rise — trips throughout Venezuela to promote his Bolivarian cause were followed by trips abroad, including one with Fidel Castro that began a close political relationship that lasted until Chávez died.

“Chávez from his time as a young military officer was a deep admirer of the Castro regime,” said Adam Isacson, a senior researcher at the Washington Office on Latin America.

His growing presence on the world stage and his support among Venezuela’s working class helped usher him into office in 1999. Despite strong rhetoric about sweeping changes, Chávez proceeded cautiously in his reform, such as lowering the country’s chronic inflation and firing the management of the state-run oil company, Petróleos de Venezuela.

The firings, paired with discontent among Venezuela’s middle and upper classes, helped prompt the 2002 coup that ousted Chávez from power for 47 hours. After regaining control, Chávez quickly blamed the United States for its alleged involvement in the coup — setting up what would be a conflict between the two nations for the remainder of his life.

Chávez’s remaining years in power were marked by his growing contempt for the U.S. and other Western powers, his courting of nations such as Iran and Cuba and sweeping socialist reforms in Venezuela.

“For the first 10 years after the Cold War, it was almost impossible to think that the people in Latin America could elect someone who didn’t oblige the interests of the United States or the wealthy,” Isacson said. “Chávez was not only elected, but was able to survive and help other leaders in Latin America survive.”

From infamously calling former President George W. Bush “the devil” in his 2006 address to the United Nations to his tongue-in-cheek gift of Eduardo Galeano’s “Open Veins of Latin America” to President Barack Obama at the Summit of the Americas to his almost weekly televised denouncements of U.S. influence on his quasi-variety show “A lo Presidente,” Chávez made a career of ruffling the feathers of the U.S.

Add his very public spat with King Juan Carlos of Spain and his call to war against former Colombian President Alvaro Uribe in the 2008 Andean Diplomatic Crisis and Chávez’s relations with the U.S. and its allies were far from cozy, to say the least.

Despite his vocal opposition to the United States hegemony in Latin America, very little changed economically between the two nations with Chávez in power. The oil-rich nation still is the U.S.’s fourth-largest importer of oil, shipping in 928,000 barrels of crude a day, according to the U.S. Energy Information Administration.

“If Chávez could have substituted the U.S. market for oil for another, preferably anti-American, market, he would have done it,” said Otto Reich, former U.S. Ambassador to Venezuela. “Venezuela needs the U.S. much more than the U.S. needs Venezuela.”

While many in the U.S diplomatic and the intelligence communities saw Chávez as an unsettling power throughout Latin America, the former Venezuelan leader made inroads with the American left thanks to his visits to impoverished neighborhoods like New York’s South Bronx, his heating-oil program in the U.S. and his offer to help victims of Hurricane Katrina.

“Chávez generally disliked the U.S., but he knew there was a line he could not cross,” Isacson said. “He knew not to mess with the flow of oil. He knew you could flirt with Iran, but not militarily — economically, diplomatically, politically, but not militarily.”

Iran has been one of the U.S.’s staunchest rivals on the world stage since the 1979 revolution that overthrew the CIA-backed Shah Mohammad Reza Pahlavi and put in power Ayatollah Khomeini and the Islamic Republic. Since then, the U.S. has tried to curb the country’s nuclear program and its influence in the world, but Chávez’s friendship with Tehran worried many in the U.S. government who saw Iranian influence creeping into the U.S.’s historical sphere of influence.

Chávez’s friendship with Iranian President Mahmoud Ahmadinejad, Cuba’s Castro brothers, the increasingly unfriendly leaders of Russia and the Bolivarian Alliance for the Americas, or ALBA, his bloc of Latin American supporters including Nicaragua’s Daniel Ortega, Bolivia’s Evo Morales and Ecuador’s Rafael Correa shifted the power in the region away from Washington and toward Caracas.

“There are a variety of Latin American countries who in the past drifted toward the U.S. who are now moving back to their Latin American roots,” Birns said of Chávez’s influence, adding that the U.S. must court the region if it wants to gain back some of its influence lost under Chávez’s time in power.

Experts argue that Chávez’s death will not dramatically change the course that he set globally in his 14 years in power. Cuba will still remain an ally and beneficiary, the U.S. will still get its oil and the country will continue to deal with “rogue states.” The only change will be the power and influence of ALBA, said Chris Sabatini, the senior policy director at the Americas Society/Council of the Americas, a nonprofit think tank in New York City.

“Ecuador’s Correa looks like he could take over, but he lacks the bombast that Chávez had,” Sabatini said. “ALBA will remain, but it will be much less flamboyant than when Chávez was at the controls.”

Maybe even more so than his legacy abroad, Chávez’s imprint in Venezuela is sharply divided.

He was adored by the country’s poor and working class for his social and economic reforms while despised by businessmen, opposition media and U.S.-friendly Venezuelans for his nationalization reforms, the dramatic rise in violent crime rates and a censoring of the media among other things.

“You either love him or you hate him,” Sabatini said. “He’s become a national obsession.”

Under Chávez, Venezuela  set-up more than 100,000 state-owned cooperatives, created “Bolivarian Missions” to provide medical, educational and other social welfare programs to poorer Venezuelans as well as increasing state spending in a number of government programs aimed at curbing the private sector.

The increase in social spending is one thing that kept Chávez in power for over a decade and built a base of poor and working class voters who became devoted “Chavistas,” or die-hard followers. It did, however, also alienate many in the country’s conservative business class, who viewed the nationalization of private sector business and widespread social programs as a drain on the economy and a swift march toward a new Cuba.

Critics also railed against the country’s skyrocketing violent crime rate and widespread corruption in the government.

Venezuela is considered to be one of the most deadly countries in the Western Hemisphere, with 19,336 homicides occurring in 2011, according to the Venezuelan Violence Observatory, a nonprofit agency that tracks violent crimes in the country. That comes out to be on average 53 murders per day — giving the country a murder rate of about 67 per 100,000 people.

The Andean nation is also ranked as one the least open societies in the world — 165 out of 174 nations on Transparency International’s 2012 Corruption Perception Index.

“It is not surprising at all,” said Alejandro Salas, Transparency International’s regional director for the Americas. “It’s a country where the president has so much power over every facet of government.”

Besides the coup attempt in 2004, the biggest threat to Chávez’s power was his health. The June 2011 announcement saying he was battling cancer foreshadowed a period of tense anxiety over the future of the country.

Under a veil of state secrecy, Chávez’s cancer battle was used by both himself and his political opponents in the country’s 2012 presidential race. After handily defeating opponent Henrique Capriles, Chávez almost immediately fled to Cuba after announcing that his cancer had returned.

He then disappeared in December from view after handing over his executive powers to Vice President Nicolás Maduro and naming the former truck driver his successor.

The silence was broken only by letters from Chávez to other world leaders and pronouncements from Maduro on his health. Maduro spoke today on Venezuelan state television, somberly announcing the president’s death and asking for the people to rally around the government. It came just hours later after Maduro had already gone before cameras to announce he was giving two U.S. military attachés a day to pack up and leave the country. That move came amid wild accusations that “enemies” of Venezuela, including the U.S., conspired to assassinate him medically through cancer.

Hugo Chávez leaves a mixed legacy in his country and throughout the world. While experts seem almost universally to agree that the Chavistas will consolidate their power in the short term, what happens to Chavismo and Venezuela in the long term remains unknown.

“Venezuela without Chávez is almost unthinkable,” Sabatini said. “The country’s situation post-Chávez is unpredictable.”