Severe Florida citrus freezes since 1880 are identified and described in terms of the horticultural damage, overall frequency of occurrence, and association with polar anticyclone outbreaks in the plains of southern Canada and the United States. The most severe “advective” freezes are associated with strong cold anticyclones having tracks southward across the plains to Texas with subsequent northeastward movement. Other anticyclones move in a track somewhat east of this and ultimately pass over Florida or the eastern Gulf of Mexico. Over 80% of the worst Florida citrus freezes are associated with anticyclones with central pressures in excess of 1045 mb moving along these paths. However, anticyclones of similar intensity with more zonally oriented paths across higher latitudes are associated with minor citrus damage. The major freezes tend to be clustered in time in the 1890s and since 1977. On interdecadal time scales, the recent freezes are not linked to higher winter mean pressure in the northern plains, and there has not been an unusually high frequency of strong anticyclones in recent decades, compared to earlier this century. Compared to the freeze-free period of 1948–57, the winters of 1977–86 are characterized by a more amplified 500-mb mean standing wave pattern across North America. This is linked to changes in the Pacific/North American upper-air teleconnection pattern, the index for which had much lower values (characterized by zonal flow) prior to 1958.