Two attempts at grand compromise have underpinned global order since the end of the Second World War. The first, a compromise between laissez-faire liberalism and domestic interventionism, famously described by John Ruggie as ‘embedded liberalism’, legitimated and stabilized a multilateral order for 50 years. A second attempt, this time between North and South at the end of the Cold War around a discourse of ‘sustainable development’, remains uneasy, conflict prone and much less institutionalized. They are compared and contrasted by asking whether they are truly compromises or reflect domination and hegemony, what conditions led to them, and what drivers of change have limited and challenged them. Ultimately, differences in their bases of legitimacy offer lessons for the prospects of building a new grand compromise in the wake of contemporary strains on global governance.