During the excavation of the Alaskan Way Viaduct replacement tunnel in Seattle, Washington, a 17.5 m diameter tunnel boring machine (TBM) nicknamed “Big Bertha” was damaged after encountering unexpected subsurface conditions. Significant dewatering of multiple aquifers was required to reach the TBM for repairs. Groundwater drawdown and soil consolidation associated with dewatering created a 0.4 km2 region of initial subsidence with maximum vertical settlements exceeding 2.5 cm between August and December 2014. Dewatering wells remained operational until January 2016 and likely contributed to observed groundwater drawdown in areas outside the region of initial subsidence. To determine how an urban landscape with complex and poorly constrained geologic and hydrologic conditions responds to an extended period of dewatering within multiple aquifers, the rate, duration, spatial extent, and magnitude of dewatering-related displacements were analyzed by combining three paths of Sentinel-1 interferometric synthetic aperture radar data spanning November 2014 to October 2019 into a time series of vertical surface deformation using the minimum acceleration algorithm. Our results show that post-dewatering ground rebound within this complex hydrogeologic system occurred at faster rates and with more significant spatial deformation variability than initial subsidence, reaching rates of up to 17 cm/year coupled with potentially hazardous differential rebounds across short distances. In addition, prolonged groundwater pumping at depths greater than 60 m appears to have induced delayed subsidence over a larger area of ∼20 km2, reaching magnitudes of up to 3 cm and lasting for over 3 years after the cessation of pumping.