Wind-induced sea level blowouts, measured as negative storm surge or extreme low water (ELW), produce public safety hazards and impose economic costs (e.g., to shipping). In this paper, we use a regional hydrodynamic numerical model to test the effect of historical environmental change and the time scale, direction, and magnitude of wind forcing on negative and positive surge events in the New York Harbor (NYH). Environmental sensitivity experiments show that dredging of shipping channels is an important factor affecting blowouts while changing ice cover and removal of other roughness elements are unimportant in NYH. Continuously measured water level records since 1860 show a trend towards smaller negative surge magnitudes (measured minus predicted water level) but do not show a significant change to ELW magnitudes after removing the sea-level trend. Model results suggest that the smaller negative surges occur in the deeper, dredged modern system due to a reduced tide-surge interaction, primarily through a reduced phase shift in the predicted tide. The sensitivity of surge to wind direction changes spatially with remote wind effects dominating local wind effects near NYH. Convergent coastlines that amplify positive surges also amplify negative surges, a process we term inverse coastal funneling.