This article from *The Surgeon's Record* explores the challenges faced by major retail players as they attempt to enter the healthcare sector, highlighting recent strategic retreats and pivots. It delves into Walmart's discontinuation of its in-store healthcare services and Humana's subsequent use of these spaces, Walgreens' financial setbacks related to VillageMD, and CVS's continued commitment to healthcare despite cost pressures. The article also discusses Amazon's healthcare strategy, including its significant investments and operational hurdles. The insights from healthcare finance expert Blake Madden provide additional context on why these retail giants struggle with healthcare ventures, emphasizing the unique challenges of integrating healthcare into their existing business models.