This article seeks to imagine a renewed common ground for critical criminologies. In this article, the quest of imagination is developed as an answer to the question: `On what kind of suffering should critical criminologies/ists be concentrating their attention?'. Looking for answers to that question, the paper explores the broad contours of our contemporary era, which is read as a `hypermodern' zone of strategized ambivalence, or ambivalent strategics. This hypermodern zone, which has seeped into the very capillaries of everyday life, is also the zone which (re)produces contingent logics of incoherence/coherence within politics of identity/difference; it is the zone of hyperflexibility, and of hyperreflexivity, of ambivalent social fragmentation/contraction, and of ambivalent communities, of ambivalent de(re)centring identities, of contingent locations of multiple, multivocal and often incoherent and contradictory voices of oppression/liberation. Answering the question: `Alternatives to what kind of suffering?', then, must take this hypermodern ambivalence into account. One way of doing so, as is argued here, is in and through a discursive praxis of `border-crossing', during which critical criminologists will find a renewed common ground only (paradoxically) while dissolving or evaporating into a radical democratic politics.