The present study investigates the two contrasting winters of 2010 and 2014 during which the North Atlantic Oscillation (NAO) was mainly negative and positive, respectively. In the North Pacific, contrasting anomalies were also present, with a straight zonal Pacific jet in 2010 and a strong poleward deviation of the Pacific jet in its exit region in 2014. Using reanalysis data sets and adopting a nonlinear initial‐value approach with a quasi‐geostrophic model, we show that the Pacific‐North American anomalies are responsible for shaping synoptic wave trains propagating across North America. This in turn largely determines the nature of wave breaking and the synoptic eddy feedback onto the mean flow in the North Atlantic and finally the NAO phase. In such a proposed mechanism, synoptic wave activity forms the cornerstone of the dynamical relationship between the North Pacific and North Atlantic large‐scale anomalies during the contrasting winters of 2010 and 2014.