This project draws upon the thought of two Canadians, philosopher George Grant and theologian Douglas John Hall, to enucleate the crisis of hope in North America at the end of the modern era, at the demise of Christendom. This crisis of hope is manifested both in a false optimism that fearfully denies and represses the reality of the darkness in all its various forms and in a despairing meaninglessness resulting from the ‘absolutization’ of relativism. As thinkers shaped by the theology of the cross and located on the fringe of the American Empire, Grant and Hall have tapped into the soul of North America and prophetically glimpsed an insidious darkness that is feverishly at play across the public and religious realm. As an exercise in a contextual theology of the cross, this project constructively appropriates the parable of the thief in the night (Mt. 24:42-44; 1 Thess. 5:1-11) to reflect both on the crisis of hope at play in North American public and religious life and to describe the character of an authentic Christian hope for the living of these days.