Based on the CMIP5 historical simulation datasets, we assessed the performance of state-of-the-art climate models in respect to the relationship between interannual variabilities of the North Pacific synoptic eddy (NPSE) and East Asian winter monsoon (EAWM). Observation (ERAInterim) shows a high negative correlation (−0.73) between the interannual variabilities of East Asian winter monsoon (EAWM) intensity and North Pacific synoptic eddy (NPSE) activity during the period of 1979~2005. Namely, a stronger (weaker) EAWM is related to a weaker (stronger) synoptic eddy activities over the North Pacific. This strong reverse relationship can be well explained by latitudinal distributions of the surface temperature anomalies over East Asian continent, which leads the variation of local baroclinicity and significantly weakens the baroclinic wave activities over the northern latitudes of 40oN. This feature is supported by the distribution of the meridional heat flux ( ) anomalies, which have negative (positive) values along the latitudes 40~50oN for strong(weak) EAWM years. In this study, the historical simulations by 11 CMIP5 climate models (BCC-CSM1.1, CanESM2, GFDL-ESM2G, GFDL-ESM2M, HadGEM2-AO, HadGEM2-CC, IPSL-CM5A-LR, MPI-ESM-LR, MPI-ESM-MR, MRI-CGCM3, and NorESM1-M) are analyzed for DJF of 1979~ 2005. Correlation coefficient between the two phenomena is −0.59, which is comparable to that of observation. Model-to-model variation in this relationship is relatively large as the range of correlation coefficient is between −0.76 (HadGEM2-CC and HadGEM2-AO) and −0.33 (MRI-CGCM3). But, these reverse relationships are shown in all models without any exception. We found that the multi-model ensemble is qualitatively similar to the observation in reasoning (that is, latitudinal distribution of surface temperature anomalies, variation of local baroclinicity and meridional heat flux by synoptic eddies) of the reverse relationship. However, the uncertainty for weak EAWM is much larger than strong EAWM. In conclusion, we suggest that CMIP5 models as an ensemble have a good performance in the simulation of EAWM, NPSE, and their relationship.