The long-term variability of sea level and surface flows in the Gulf of Mexico (GOM) is studied using global monthly sea level reconstruction (RecSL) for 1900–2015. The study explored the long-term relation between the dynamics of the GOM and inflows/outflows through the Yucatan Channel (YC) and the Florida Straits (FS). The results show a century-long trend of increased mean velocity and variability in the Loop Current (LC); however, no significant upward trend was found in the YC and FS flows, only increased variability. Empirical orthogonal function (EOF) analysis of sea surface height found spatial patterns dominated by variations in the LC and temporal variations on time scales ranging from a few months to multidecadal. The time evolution of each EOF mode of sea level is correlated with the velocity of either the LC, the YC, or the FS or some combination of the different flows. The mean sea level difference between the GOM and the northwestern Caribbean Sea was found to be influenced by the North Atlantic Oscillation (NAO), with unusually high differences during the 1970s when the NAO index was low and the Atlantic Ocean circulation was weak. Extreme peaks in SL difference coincide with the extension of the LC and the seasonal eddy shedding pattern. The observed seasonal cycle in the extension area of the LC as obtained from 20 years of altimeter data is significantly correlated (R?=?0.63; confidence level?=?98%) with the seasonal YC flow obtained from 116 years of the RecSL data. However, the same LC extension record had lower correlation (R?=?0.45; confidence level?=?90%) with the observed YC transport obtained from direct moored measurements over?~?5 years, indicating the need for much longer measurements, since the LC extension and the YC flow are strongly affected by interannual and decadal variations. The study demonstrates the usefulness of even a coarse-resolution reconstruction for studies of regional ocean variability and climate change over longer time scales than current direct observations allow.