Soapbox Are you old enough to remember Hurricane Gilbert? – On this day in Jamaican History 6 years agoby Soapbox Fi Mi On September 12, 1988 Hurricane Gilbert hit Jamaica as a Category 4 storm. Approximately 45 people lost their life. Gilbert was the most severe hurricane to hit Jamaica since Hurricane Charlie in 1951. The storm left $4 billion (1988 USD) in damage.