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Regarding his native country, which he visited just once after going into voluntary exile, Bolaño had conflicted feelings. He was notorious in Chile for his fierce attacks on Isabel Allende and other members of the literary establishment. "He didn't fit into Chile, and the rejection that he experienced left him free to say whatever he wanted, which can be a good thing for a writer", commented the Chilean novelist and playwright Ariel Dorfman.

In 2003, after a long period of declining health, Bolaño died. It has been suggested that he was at one time a heroin addict and that the cause of his death was a liver illness resulting from Hepatitis C, with which he was infected as a result of sharing needles during his "mainlining" days. However, the accuracy of this has been called into question. It is true that he suffered from liver failure and was close to the top of a transplant list at the time of his death.

Six weeks before he died, Bolaño's fellow Latin American novelists hailed him as the most important figure of his generation at an international conference he attended in Seville. Among his closest friends were the novelists Rodrigo Fresán and Enrique Vila-Matas, and Fresán's tribute included the statement that "Roberto emerged as a writer at a time when Latin America no longer believed in utopias, when paradise had become hell, and that sense of monstrousness and waking nightmares and constant flight from something horrid permeates 2666 and all his work." "His books are political", Fresán also observed, "but in a way that is more personal than militant or demagogic, that is closer to the mystique of the beatniks than the Boom." In Fresán's view he "was one of a kind, a writer who worked without a net, who went all out, with no brakes, and in doing so, created a new way to be a great Latin American writer." Larry Rohter of the New York Times, said "Bolaño joked about the 'posthumous', saying the word 'sounds like the name of a Roman gladiator, one who is undefeated', and he would no doubt be amused to see how his stock has risen now that he is dead."

Bolaño was survived by his Spanish wife and their two children, whom he once called "my only motherland." (In his last interview, published by the Mexican edition of Playboy magazine, Bolaño said he regarded himself as a Latin American, adding that "my only country is my two children and perhaps, though in second place, some moments, streets, faces or books that are in me…") Bolaño named his only son Lautaro, after the Mapuche leader Lautaro, who resisted the Spanish conquest of Chile, as related in the sixteenth-century epic La araucana. His other child, a daughter, was named Alexandra.

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