Summary: Category captainship, the approach where retailers use manufacturer-retailer collaboration, is a common way to leverage resources and capabilities in order to improve the sales/shelf performance ratio. However, evidence suggests that the depth and effectiveness of category captains and collaboration in retail are not as high as theory or best practice would predict. Suppliers and retailers suspect each other of opportunistic behaviour detrimental to both. In a stylized dyadic supply chain model prior to the effective contracting of the category captain, we show why information asymmetry between both is preferred: the retailer will hint at or develop retaliatory power to keep the supplier in check whereas the supplier will try to extract a rent by taking advantage of available information about relationship specific investment. We model single-period interaction when the retailer has to invest in relationship specific assets and alternative category manager grooming. We provide normative and positive support both to the captain’s potential opportunistic behaviour as well as the retailer’s investment decision in alternative captains and monitoring ability. In a two-period extension, we show how the retailer can discipline the captain ex ante. The model and its results complement and extend research in pre-contractual category captainship and supplier-retailer collaboration and coordination. They represent a departure from the usual vision in which sharing information and collaborating generate higher supply chain rent.