This chapter analyzes the intersection between the 2021 presidential election and the 2021–2022 constitutional process. It focuses on a decisive period that reshaped the political landscape of the nation. Gabriel Boric’s victory and his coalition, Apruebo Dignidad, mirrored a public rejection of the political establishment in favor of far-left, transformative ideals induced by the social outburst. Boric’s ascent, bolstered by a generational movement and victory over the Communist Party’s Daniel Jadue in the presidential primaries, embodied a combination of grassroots activism and radical ambition that resonated with a frustrated electorate. However, embracing this systemic overhaul posed significant risks. Rooted in divisive rhetoric and promises of sweeping change, Boric’s campaign sidelined the center-left and -right while raising expectations for reform to unsustainable levels. The constitutional process, which was characterized by both fragmentation and polarization, became further entangled with Boric’s victory, thus amplifying political uncertainty. While his ascension symbolized a rupture in post-transition stagnation, it exposed the costs of the pursuit of untested leadership and radical reform. Chile’s choice, while hopeful for renewal, fostered instability, deepened societal divisions, and highlighted the challenges of balancing transformation and governance.