Trust is fundamental to safety culture, and its absence reduces cooperation. In high-risk industries, cooperation between different actors is crucial to preventing accidents, which requires relationships of trust between controllers, contractors, and providers. This study examines case studies to determine how the “company man” role affects these relationships of trust, influencing performance, cooperation, and safety in well construction operations. The analysis reveals that mistrust undermines cooperation and is linked to the fear of opportunistic behavior. Contractors have discretionary power in assigning penalties, and there is heterogeneity among company men. Although opportunities for cooperation improve performance and safety, a fragile level of trust prevents progress. The company man’s actions affect trust and cooperation between the contractor and the operating company, shaped by organizational issues. These relationships become fragile unless they are reflected upon, jeopardizing operations’ efficiency, learning, and safety. This study faces limited access to the field and the scarcity of research in this context.