There are a number of clear examples in the instrumental period where positive El Niño-Southern Oscillation (ENSO) events were coincident with a severely weakened Indian summer monsoon (ISM). ENSO's influence on ISM precipitation has therefore remained the centerpiece of various predictive schemes of ISM rainfall for over a century. The teleconnection between ISM precipitation and ENSO has undergone a protracted weakening since the late 1980s, suggesting the strength of ENSO's influence on ISM precipitation may vary on multidecadal timescales. The recent weakening has occurred despite the fact that the ENSO system has experienced variance levels during the latter part of the 20th century that are as high as any period in the past millennium. The recent change in the ENSO-ISM coupling has prompted questions as to whether this shift represents a natural mode of climate variability or a fundamental change in ENSO and/or ISM dynamics due to anthropogenic warming or aerosol impacts on the ISM. Here we place the 20th century ENSO-ISM relationship in a millennial context by assessing the phase relationship between the two systems across the time spectrum using a a series of high-resolution reconstructions of ENSO and the ISM from tree rings, speleothems and corals. The results from all the proxies suggest that in the high-frequency domain (5-15 yr), warm (cool) sea surface temperatures in the eastern tropical Pacific lead to a weakened (strengthened) monsoon. This finding is consistent with the observed relationship between the two systems during the instrumental period. However, in the multidecadal domain (30-90 yr) the phasing between the systems is reversed such that periods of strong monsoons were, in general, coincident with periods of enhanced ENSO variability. This result is counterintuitive to the expectation that enhanced ENSO variance favors an asymmetric increase in the frequency of El Niño events and therefore a weakened monsoon system. The finding implies that the prominent multidecadal variability that characterizes the last 1000 yr of the ISM is not likely attributable to multidecadal shifts in ENSO. If there is a continued trend towards enhanced ENSO variance in the coming decades, the results presented here do not suggest this will force a reduction in ISM precipitation.