Gamble Rogers was a native Floridian who started his professional career with the Serendipity Singers but soon went out on his own to create a combination of music and story-telling that made him a favorite on the Southeastern college circuit. He lived in St. Augustine and, when in town, would perform at the Tradewinds Lounge - another local institution. Jimmy Buffett often toured with him as his warm-up act before he became famous. Jimmy went on to fame and fortune, but when Gamble died saving a man from drowning in 1991 he became a legend.