Previous studies have suggested that, in the zonal mean, the climatological Northern Hemisphere wintertime eddy-driven jet streams will weaken and shift equatorward in response to Arctic amplification and sea ice loss. However, multiple studies have also pointed out that this response has strong regional differences across the two ocean basins, with the North Atlantic jet stream generally weakening across models and the North Pacific jet stream showing signs of strengthening. Based on the zonal wind response with a fully coupled model, this work sets up two case studies using a barotropic model to test a dynamical mechanism that can explain the differences in zonal wind response in the North Pacific versus the North Atlantic. Results indicate that the differences between the two basins are due, at least in part, to differences in the proximity of the jet streams to the sea ice loss, and that in both cases the eddies act to increase the jet speed via changes in wave breaking location and frequency. Thus, while baroclinic arguments may account for an initial reduction in the midlatitude winds through thermal wind balance, eddy–mean flow feedbacks are likely instrumental in determining the final total response and actually act to strengthen the eddy-driven jet stream.