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The ability to accurately measure ocean surface wind vectors from space in all weather conditions is important in many scientific and operational usages. One highly desirable application of satellite-based wind vector retrievals is to provide realistic estimates of tropical cyclone intensity for hurricane monitoring. Historically, the extreme environmental conditions in tropical cyclones (TCs) have been a challenge to traditional space-based wind vector sensing provided by microwave scatterometers. With the advent of passive microwave polarimetry, an alternate tool for estimating surface wind conditions in the TC has become available. This paper evaluates the WindSat polarimetric radiometer's ability to accurately sense winds within TCs. Three anecdotal cases studies are presented from the 2003 Atlantic Hurricane season. Independent surface wind estimates from aircraft flights and other platforms are used to provide surface wind fields for comparison to WindSat retrievals. Results of a subjective comparison of wind flow patterns are presented as well as quantitative statistics for point location comparisons of wind speed and direction.