This chapter is concerned with evaluating the capacity of three different types of creative grammar to service art education ‘as if’ for ‘future flourishing’, an emphasis that requires drawing on the claims of wisdom and its corollary of ‘generative wisdom’ (Solomon et al. 2005). Reconfiguring art education as a form of strategic wisdom requires specifying the conditions for cultivating creativity, knowledge and understanding that is consistent with an ethical vision, a sense of wonder, and a better approach to promoting flourishing on this planet. This aim contrasts with forms of learning, creativity and living that have been in ascendancy in late-and post-modernity, which have emphasised so-called cognitive reliability over ethical responsibility; nihilism, narcissism and narrow desires and pursuits over the promotion of the common good and its corollary of the practice of deep ecology.