Tropical cyclones (TCs) often change intensity as they move over mesoscale oceanic features, as a function of the oceanic mixed layer (OML) thermal response (cooling) to the storm's wind stress. For example, observational evidence indicates that TCs in the Gulf of Mexico rapidly weaken over cyclonic cold core eddies (CCEs) where the cooling response is enhanced, and they rapidly intensify over anticyclonic warm features such as the Loop Current (LC) and Warm Core Eddies (WCEs) where OML cooling is reduced. Understanding this contrasting thermal response has important implications for oceanic feedback to TCs' intensity in forecasting models. Based on numerical experimentation and data acquired during hurricanes Katrina and Rita, this dissertation delineates the contrasting velocity and thermal response to TCs in mesoscale oceanic eddies. Observational evidence and model results indicate that, during the forced stage, the wind-driven horizontal current divergence under the storm's eye is affected by the underlying geostrophic circulation. Upwelling (downwelling) regimes develop when the wind stress vector is with (against) the geostrophic OML velocity vector. During the relaxation stage, background geostrophic circulations modulate vertical dispersion of OML near-inertial energy. The near-inertial velocity response is subsequently shifted toward more sub-inertial frequencies inside WCEs, where rapid vertical dispersion prevents accumulation of kinetic energy in the OML that reduces vertical shears and layer cooling. By contrast, near-inertial oscillations are vertically trapped in OMLs inside CCEs that increases vertical shears and entrainment. Estimates of downward vertical radiation of near-inertial wave energies were significantly stronger in the LC bulge (12.1X10 super -2 W m super -2) compared to that in CCEs (1.8X10 super -2 W m super -2). The rotational and translation properties of the geostrophic eddies have an important impact on the internal wave wake produced by TCs. More near-inertial kinetic energy is horizontally trapped in more rapidly rotating eddies. This response enhances vertical shear development and mixing. Moreover, the upper ocean temperature anomaly and near-inertial oscillations induced by TCs are transported by the westward-propagating geostrophic eddies. From a broader perspective, coupled models must capture oceanic features to reproduce the differentiated TC-induced OML cooling to improve intensity forecasting.