This study investigates the contributions of incipient vortex circulation and mid-level moisture to tropical cyclone (TC) expansion within an idealized numerical modeling framework. We find that the incipient vortex circulation places the primary constraint on TC expansion. Increasing the mid-level moisture further promotes expansion but mostly expedites the intensification process. The expansion rate for initially large vortices exhibits a stronger response to increasing the mid-level moisture compared to initially small vortices. Previous studies have noted a proclivity for relatively small TCs to stay small and relatively large TCs to stay large; that is, TCs possess a sort of “memory” with respect to their incipient circulation. We reproduce this finding with an independent modeling framework and further demonstrate that an initially large vortex can expand more quickly than its relatively smaller counterpart; therefore, with all other factors contributing to expansion held constant, the contrast in size between the two vortices will increase with time. Varying the incipient vortex circulation is associated with subsequent variations in the amount and scale of outer-core convection. As the incipient vortex circulation decreases, outer-core convection is relatively scarce and characterized by small-scale, isolated convective elements. On the contrary, as the incipient vortex circulation increases, outer-core convection abounds and is characterized by relatively large rainbands and mesoscale convective systems. A combined increase in the amount and scale of outer-core convection permits an initially large vortex to converge a substantially larger amount of absolute angular momentum compared to its relatively smaller counterpart, resulting in distinct expansion rates.