The Philippine left’s short-lived association with the government of Rodrigo Duterte from 2016 vexed political observers, whether sympathetic to or critical of the left. Against the charge that the left was simply subordinated as a political force to Duterte’s multi-class populist-cum-fascist project, this article argues that the left was both friend and foe of Duterte, who promised an aggressive War on Drugs as well as socioeconomic reforms. It situates the left–Duterte relationship within the history of engagement by new political actors with elite democracy in the Philippines since 1987. The friend-and-foe or dual strategy analysis uncovers some of the richness of the left’s progressive engagement with Duterte. This contributes to an understanding of Philippine political history by providing a profile of progressive engagement involving a set of actors different from those who have previously been analysed – viz. national democrats rather than social democrats – and an increasingly authoritarian administration explicitly espousing anti-human rights rhetoric. We specify the conditions for the emergence of the left–Duterte relationship, how it unfolded, and the tipping points that led to its collapse. The findings underscore the complexities and extreme difficulty of transforming Philippine politics through progressive engagement.