Armed and non-armed insurgencies of peasants, small farmers, Indigenous peoples, Afro-Colombians, and other subaltern groups are a defining feature of Colombian history. These multiple insurgencies have broadly demanded, individually or collectively, a restructuring of capitalism by redistributing land (arguably, the heart of Colombia’s civil war) and various forms of state restructuring that demand intervention to address deep socioeconomic inequalities. The latest iteration of such insurgencies occurred in April 2021 when a national strike broke out in response to the right-wing government of Ivan Duque's proposal for a tax that targeted, among other items and assets, staples such as sugar and coffee. The revolt rapidly spread across the national territory and escalated into violent confrontations between protesters and the Colombian anti-riot police (a force well-recognized for their brutality). What were the demands of the “insurgent” protesters? Free college education, health services, higher wages, jobs, land redistribution, and recognition of Indigenous and Afro-Colombians' human rights. The strike forced the government to retract the tax (their only action on the demands), but not before government institutions criminalized the protesters, most of whom were youth seeking a better future. In this paper, I examine the history of the insurgency-led conflict in Colombia as a long-term legacy of Spanish colonization, the Cold War, and the neo-colonization of Latin America by the United States. In so doing, the paper contributes to understanding the current global crisis of the state and various forms of insurgencies from Colombia as a geopolitical location. The paper shows that while the struggle for land access/ownership remains at the center of the conflict, para-state armies, narco-trafficking and extractive economies shape the formation of new cycles of insurgency and counterinsurgency in the country.