The detection and quantification of strong sea surface winds, reaching up to 25 m·s−1, whether associated with deep convection aloft or not, have been extensively discussed in previous studies. This method involves the combined observation of the same event from both low‐orbit altitude and geostationary (GEO) satellites. Strong surface winds observed by the Sentinel‐1 C‐band synthetic aperture radar (SAR) are robustly associated with deep convective clouds detected by GEO infrared sensors. The current paper aims to generalize the previous assessment of several convective wind events by collecting a larger dataset and comparing these data to in‐situ wind observations. To achieve this, we evaluated wind speeds retrieved from Sentinel‐1 SAR images against corresponding in‐situ wind measurements from all active buoys/stations in the Gulf of Mexico. Significant agreement between satellite‐based winds and in‐situ data was achieved, particularly for wind speeds exceeding 3 m·s−1, with even better agreement for wind speeds over 10 m·s−1. From this dataset, three specific convective cases were extracted to illustrate various stages of convective squall events: before, during, and after the occurrence of a squall peak. In each case, comparison with in‐situ measurements showed that SAR‐estimated wind speeds closely matched observed speeds, including the peak convective winds, which were estimated at 18.90 m·s−1 and measured at 20.69 m·s−1. Furthermore, combining these findings with GOES‐16 sequential images illustrates the temporal and spatial similarity between deep convection areas, estimated strong sea surface wind patterns, and measured wind speeds.