The effective transport of cargo across the globe by aircraft, termed strategic airlift, is foundational to the success of humanitarian aid/disaster relief (HA/DR) missions and even military operations. Due to the variable extremity of these events, it is essential for aircraft and operations to be designed with a high resilience, factoring in performance in a plethora is scenarios. This work aims to provide a framework that enables the coupling of aircraft, fleet and concepts of operations (CONOPS) design to a mission effectiveness in a strategic cargo airlift. Through agent-based modelling, the complex interaction and emergent behaviors of the different systems in the dynamic airlift environment is better captured and evaluated. Unexpected events, such as cargo requirement reformulation, aircraft servicing and changing airbase accessibility, are employed to emulate the dynamic and spontaneous nature of rapid cargo airlift missions. The impact of these events is stochastically modelled, promoting an analysis of a variety of scenarios. By creating a theoretical disaster relief mission, a trade-space exploration is conducted so that aircraft designs and operational objectives can be evaluated for their mission effect. The framework demonstrates the ability to evaluate aircraft and operational performance holistically, enabling a more robust design procedure for a variety of potential design scenarios and metrics.