The Gouldian argument for evolutionary contingency found in Wonderful Life can be dissected into three premises: palaeontological, macro-evolutionary, and developmental. Discussions of evolutionary contingency have revolved primarily around the developmental. However, a shift in methodological practice and new palaeontological evidence subsequent to the book’s publication appears to threaten the palaeontological premise that asserts high Cambrian disparity, or, roughly, that morphological differences between the Cambrian species were high. This presents a prima facie problem: Did the Cambrian consist of enough anatomical variety to fuel a different outcome upon a replay of the tape of life? I investigate the role that disparity plays in the Gouldian argument for evolutionary contingency and conclude that the reduced disparity view does not undermine the argument, per se. As for the macro-evolutionary premise, Gould never offers any explicit justification for the idea that species sorting was indiscriminate or ‘lottery-like’ (though he certainly gestures at it). Putting aside the exegetical, I consider certain empirical avenues for underwriting the macro-evolutionary premise and argue that the most plausible route is to appeal to the special status of mass extinctions, a move that is not entirely unfamiliar to macro-evolutionists. That is, mass extinctions can be good sources of contingency due to their being ‘chancy’ in at least three respects. In sum, I update the palaeontological and macro-evolutionary premises as to reconstrue the Gouldian argument for evolutionary contingency in its strongest form.