Dr. Robert “Bob” Winquist reflects on a career that helped redefine orthopedic trauma, tracing his path from an unexpected pivot away from internal medicine to pioneering closed intramedullary nailing in North America. He describes the early skepticism, technical improvisation, and mentorship—especially from Ted Hansen—that shaped his work and the landmark femoral nailing publication that shifted global practice. Winquist’s stories reveal how perseverance, clarity of thought, and a commitment to “doing what’s right” accelerated the adoption of closed nailing despite resistance. Now fully retired by deliberate choice, he shares insights on teaching, decision-making, and life beyond surgery, offering a rare look into the formative years of modern trauma care.