This article seeks to understand the manner in which the commitment to freedom of expression has evolved in both Canada and Colombia, based on the examination of historical patterns and court decisions. Through the lens of the Canadian experience, it looks at the difﬁculties faced by Colombia, where the state is still struggling to exercise the monopoly of power within its own territory as a ﬁrst stumbling block to the consolidation of its democracy. Any effort to compare the exercise of liber- ties in two countries with such different legal traditions faces obvious challenges, even more so when after 200 years of independence one of the countries has still failed to achieve the stability and security required to assure sustainable economic development. However, in the 21st century the principles underlying the political and economic systems of both countries are the same, and they share, at least formally, a commitment to respect democracy, human rights and principles of good government. This is the primary motivation behind this analysis.