TIMOR-Leste with its about 1.3 million inhabitants is one of the world’s smallest nations. Yet, the country’s national press council is the second biggest in the world, after Indonesia. This paradox has come about as a result of Timor-Leste’s long struggle for independence and democracy and the realization that without the freedom of the press, neither independence nor democracy could have been attained. Freedom of the press is a pillar of democracy as citizens and policymakers of democracies need the free and timely flow of information to make the informed decisions on which democracies are built and stand. While the traditional press has no monopoly of being a source or analyzer of information, especially with the advent of social media, the importance of the press could probably best be understood if we tried to imagine a world without it.