AbstractClimate anomalies over North America and Europe are closely related to the North Atlantic Oscillation (NAO). The persistence, decay or switch of the NAO phase across the boreal winter determines whether the NAO‐related climate anomalies are sustained, weakened or reversed during the boreal winter. This study compares the spatiotemporal evolution of atmospheric wind and sea surface temperature (SST) anomalies over the North Atlantic corresponding to persistence and switch of the NAO phase across the boreal winter. It is revealed that the persistence of the NAO from early to late winter is associated with a strong coupling between the NAO and the North Atlantic tripole SST anomalies. The formation of the tripole SST anomalies is attributed to the wind‐related surface latent heat flux changes. The tripole SST anomalies feedback on the NAO through eddy‐mean flow interaction. In contrast, during the winters with the switch of the NAO phase, the North Atlantic SST anomalies follow the wind changes, but do not have obvious feedback on the NAO. Our analysis identifies a prominent change of the winter NAO evolution in the early 1990s. The NAO switches its phase from early to late winter during 1970s through the early 1990s, but tends to maintain its phase during the boreal winter after the early 1990s. This interdecadal change appears to be related to the mean SST change. The SST increase in both the tropical and mid‐latitude North Atlantic Ocean in the early 1990s enhances the feedback of the NAO‐induced tripole SST anomalies on the NAO.