Strategic alliances have occurred in many western world town centers in the last decades in order to meet competition from out-of-town shopping centers. In Sweden the strategic alliance scheme called Town Center Management (TCM) is common, including stakeholders such as retailers, property owners and local authorities. The retailing in a town center is known to be the most important area to focus when the TCM is creating its strategy to attract visitors. It is the contributions from the stakeholders which makes the strategic alliance move forward towards its strategical goal. The stakeholders must know what they are expected to contribute with. If there are gaps between what is expected from a stakeholder and what is contributed, the alliance will not reach its goals. Previous research regards all retailers the same which might create inaccurate expectations. This study explores stakeholders’ perceptions of the contribution of retailing in TCMs, specifically focusing on small retailers. Small retailers with their specific characteristics, have not been acknowledged in TCM research. The theoretical contribution of this study is added knowledge on how strategic alliances are affected by the characteristics of the stakeholders in it and the context surrounding them, but also a discussion on how alliances are affected by gaps between what stakeholders in alliances expects from each other and what they contribute with. For TCM research the contribution of a more nuanced view on retailers in TCMs is added, acknowledging retailers that are small. In a case study including 31 semi-structured interviews, three gaps where identified where the stakeholders expected more from the small retailers than what was contributed. The gaps concerned the retailers store qualities, participation and attitudes. The reasons for the gaps were explored concluding that small retailers, because of their smallness, cannot contribute according to the stakeholders (including the small retailers own) expectations. The gaps where interpreted as causing difficulty for the TCM to reach its goals in the retail area. TCMs with mainly small retailers is at risk of failure as long as there are gaps between what is expected from the small retailers and what they can actually contribute with. The practical implications of this study is that in town centers where small retailers are established, the strategy and expectations must be adapted to small retailers’ characteristics. The stakeholders in TCMs must acknowledge if there are many small retailers in the town centre where they operate and be aware of their limitations (and strengths) when creating a strategy. Competing with out-of-town shopping centers otherwise will be fruitless.