Focusing on competitive dynamics, this study examines the strategic issues Boeing has faced in seeking to maintain its leading position in the airline industry. Boeing’s status as a first mover in the aerospace industry has made it a world-leading company; however, the external environment and various pressures have allowed Airbus to emerge as a strong competitor. By conducting a descriptive case analysis, this paper identifies the competitive issues between these two giants, analyzing continuous action and reaction processes throughout the whole history of the airline industry. Finally, by examining Boeing’s main strengths, business diversification options, and risk-taking culture, this paper suggests ways Boeing can retake its place as the industry leader.