Field-based case studies are uniquely suited to exploring the complex challenges of digital transformation. We propose that real discussion cases (developed from rigorously-researched field-based case studies) can trigger useful discourse that helps scholars improve theories addressing complex digital transformation challenges. To advance this argument we undertook an extreme-case study to examine the practices and theoretical contributions of an exceptionally impactful researcher in a non- IT domain (Sumantra Ghoshal, an international management scholar who conducted many field- base case studies and produced many real discussion cases). Based on our extreme-case study findings we consider implications for research on digital transformation.