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Lenny - 1999
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Hurricane Lenny Near Peak Intensity South of Puerto Rico

A broad area of low pressure was detected in the southwest Caribbean Sea on November 8, and on November 13, satellite imagery revealed that the system was organizing rapidly, and a hurricane hunter flight later that day found a closed circulation, and Tropical Depression Sixteen, the last of the year, was born about 150 miles south of the Cayman Islands. By the 14th, the depression had organized enough to become Tropical Storm Lenny at 7 am EST. Lenny tracked on a highly unusual path, moving in a eastward direction through the Caribbean, the first storm to do so in over 113 years. Rapid intensification in the warm Caribbean waters began immediately after Lenny became a tropical storm, and it strengthened into a hurricane with winds of 80 mph in less than 12 hours, with the pressure dropping 12 mbar in that time. Lenny briefly reached Category 2 strength on November 15, with winds of 100 mph, but the storm weakened temporarily later on the 15th. More strengthening began on November 16, when the storm was south of Hispaniola and curving to the ENE. Lenny was a powerful Category 3 major hurricane as it passed to the south of Puerto Rico early on November 17, and was now moving to the NE.

The intensification made Lenny into a 155 mph Category 4 hurricane on the borderline of Category 5 later on the 17th with a pressure of 933 mbar which would be its peak intensity. The powerful hurricane pounded St. Croix and the U.S. Virgin Islands at this time, but the brunt of the winds were to the south of the eye, and the islands did not receive the highest winds, as Lenny was to the south of them. Lenny slowed greatly in forward speed during this time as its intensity gradually declined. Despite remaining in a favorable environment, Lenny weakened steadily though the day on November 18, possibly due to upwelling as the storm sat over waters that were stirred and cooled by its wake. As the center drifted over St. Martin and Anguilla on the afternoon of the 18th, the storm was weakening rapidly, and was a 100 mph Category 2 storm by the time it struck Anguilla. St. Barthelemy was struck on the 19th while Lenny was a minimal hurricane, and the storm made its final landfall in Antigua later on November 19 as a tropical storm. Lenny followed an erratic path after moving into the open Atlantic waters, first moving to the ESE, and then turning back to the NE and weakening to a tropical depression.

The depression moved NE, and then moved back to the east and slowed in speed before it finally dissipated on November 23 when about 600 miles east of the Leeward Islands. Lenny was a very destructive storm, killing seventeen in its path through the islands. The majority of the fatalities were assumed to be due to freshwater flooding from the heavy rains of the storm. Damages were severe in the island of the northwest Caribbean, damaging buildings, crops, and boats in St. Croix, St. Martin, and St. Lucia. There were also reports of damage in Grenada, Guadeloupe, St. Vincent, Montserrat, and the Grenadines. Losses total 330 million US Dollars in Puerto Rico and the U.S. Virgin Islands. As spoken before, Lenny was a very odd and unusual storm. The storm tracked in an eastward direction through its whole life, and also was the strongest hurricane on record in the Atlantic Basin in the month of November with winds peaking just under Category 5 strength at 155 mph. Lenny was also the fifth Category 4 or higher storm of the 1999 Atlantic Hurricane Season, which broke the record for the amount of storms of that intensity in a single season. The record was tied in the 2005 season. The name Lenny was retired in the Spring of 2000 due to the damages and casualties, and was replaced by Lee when the list was used again in 2005.