The East Asian Winter Monsoon (EAWM) and Siberian High (SH) are inherently related, based on prior studies of instrumental data available for recent decades (since 1958). Here we develop an extended instrumental EAWM index since 1871 that correlates significantly with the SH. These two indices show common modes of variation on the biennial (2–3 year) time scale. We also develop an index of the pressure gradient between the SH and the Aleutian Low, a gradient which critically impacts EAWM variability. This difference series, based on tree-ring reconstructions of the SH and the North Pacific Index (NPI) over the past 400 years, shows that the weakening of this gradient in recent decades has not been unusual in a long-term context. Correlations between the SH series and a tree-ring reconstruction of the El Niño-Southern Oscillation (ENSO) suggest a variable tropical-higher latitude teleconnection.