This chapter examines Chile’s 2021–2022 Constitutional Convention, a historic effort to draft a new constitution in response to the social outburst in 2019. It recounts the inaugural day of the Convention and highlights its symbolic significance and the remarkable dominance of left-leaning and independent representatives. It explores how these groups leveraged their majority to design internal rules that streamlined the drafting process in their favor. The discussion then shifts to an analysis of member positions and coalition dynamics, thus exploring how ideological alignments shaped the drafting of the proposal. Subsequently, the chapter examines the content of the draft, which included ambitious provisions such as plurinational recognition, extended social and environmental rights, and a de facto unicameral legislative system. Although these elements resonated with progressive ideals, they also risked alienating moderate voters at a critical crossroads. The final section considers the trends leading up to the September 2022 plebiscite, in which it which the draft was overwhelmingly rejected by 62% of voters. Through this lens, the chapter reveals the challenges of striking a balance between transformative aspirations and public consensus and offers insights into the risks of ideological dominance in a fragmented political landscape.