Over the past 10 years, several countries in Latin America have experienced profound political and economic turbulence, wherein we can observe, through public opinion data, a deepening of the crisis of political representation. This crisis has opened windows of opportunity for anti-political discourses to gain legitimacy and for anti-political leadership to ascend to institutional spaces of representation. This chapter analyzes the worsening of the representation crisis in Brazil, Mexico, and Peru and how this crisis enabled the rise of digital political leadership in these countries over the two last decades. To this end, aggregates data from the Latinobarometer and data mined from digital social media. The results indicate that from the current scenario of the worsening representation crisis, this new type of leadership emerged, the digital political leader, who has in digital social media their main platform for establishing representative bonds and, in anti-politics, their main discursive argument.