Tropical Storm Fay (2008)

Tropical Storm Fay was the sixth tropical storm of the 2008 Atlantic hurricane season. Tropical Storm Fay caused flooding in Haiti, the next three storms would do that same thing (Gustav, Hanna, and Ike). Tropical Storm Fay made landfall in Florida four times, beating a record from Hurricane Gordon in 1994, which made landfall in Florida three times. Fay left $560 million in damage and killed 36 people.
Meteorological history.
Fay started as a tropical wave off of Africa on August 7. It did not become a tropical depression until August 15. Shortly later it became Tropical Storm Fay. Fay then crossed Dominican Republic and Haiti. 
Fay continued west and made two landfalls in Cuba. One in Cabo Cruz on August 17 and Cienfuegos on August 18, at both landfalls Fay had winds of 50 mph. 
Fay made its first landfall in Florida at Key West also on August 18 winds were at 60 mph. 
The next day Fay made landfall in Cape Romano, Florida while winds were at 65 mph. Fay moved over Florida and strangely strengthened while over Florida. Fay moved off of Florida near Melbourne. Fay moved north just off of Florida and made another landfall in Flagler Beach, Florida on August 21 while winds were at 65 mph. 
Fay moved into the Gulf of Mexico and then made her fourth and final landfall in Florida on August 23. Fay became extratropical on August 27 and also died on August 27. 
Aftermath.
Even though Fay caused a lot of damage it was not retired, Fay is on the list of names in 2014.