This study seeks to analyze the physical and dynamical mechanisms behind the wind field expansion using model simulations of a representative transition case, North Atlantic Tropical Cyclone Bonnie of 1998. The acceleration of the wind field along the outer periphery of the cyclone is found to be a function of the net import of absolute angular momentum within the cyclone's environment along inflowing trajectories. This evolution is shown to be a natural outgrowth of the development of isentropic conveyor belts and asymmetries associated with extratropical cyclones. Asymmetries in the outer core wind field manifest themselves via the tightening and development of height and temperature gradients within the cyclone's environment. Outward movement of the radial wind maximum occurs coincident with integrated net cooling found inside of the radius of maximum winds. Tests using a secondary circulation balance model show the radial wind maximum evolution to be similar yet opposite to the response noted for intensifying tropical cyclones with contracting eyewalls.