This podcast episode discusses the decline and sale of Walgreens, a century-old American pharmacy chain, to a private equity firm for $10 billion—a significant drop from its previous $100 billion valuation. The interview details the company's struggles with declining pharmacy reimbursement rates, failed diversification strategies (including expansion into retail and healthcare clinics), and missed opportunities to merge with insurance companies, ultimately leading to its sale. A key factor highlighted was Walgreens' inability to maintain its leverage against pharmacy benefit managers (PBMs) after losing a major contract with Express Scripts. The sale is presented as a potential turning point, but its success depends on the private equity firm's ability to implement effective turnaround strategies.