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.

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