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This article analyses how Timor Leste has managed to build and sustain democracy despite grinding poverty, a miniscule middle class, imperfect political institutions and the ravages of war. It challenges structural arguments and argues instead that the country’s positive trajectory is largely due to the nature of its long armed struggle against the Indonesian state. The body of the paper shows how the legacies of war on state institutions, political parties and political elites enabled the country to establish democracy against the odds. The paper concludes by putting the Timorese case in comparative perspective with Mozambique, Haiti and (possibly) other cases.