The complexity of Jimmy Buffett

Beyond Margaritaville, the beloved troubadour was a man of intellect and a humanitarian

September 18, 2023 4:59 am

Jimmy Buffett performs at a Get Out the Vote rally for U.S. Senator Bill Nelson (D-Fla.) and Florida Democratic governor candidate Andrew Gillum at the Meyer Amphitheatre on November 03, 2018, in West Palm Beach, Florida. (Joe Raedle/Getty Images)

Jimmy Buffett died, and I started thinking about Key West. 

Like Buffett, my father-in-law, Frank E. Taylor, chose Key West as a less conventional refuge. For about a decade, my husband and I, and then our two daughters, spent a couple of weeks with him every winter. Even though it’s been years since our last visit, I still remember stepping off the small plane into the tiny Key West International Airport. The sweet, tropical air was instant balm for the soul for those of us trying to escape northern weather. 

Frank’s Key West was not a foggy idyll of drugs, sun and tequila. It was rather literary Key West. While we sat on beaches, collected coconuts, and rode our bikes to restaurants cantilevered over the water to drink tropical cocktails and eat conch fritters, we also met writers like novelists John Hersey and David Kaufelt, and the poet James Merrill.  There was no escaping the pervasive Margaritaville vibe, which included a daily, wonderful, riotous salute to the setting sun each evening. It also encompassed some pretty unpleasant encounters with barefoot drunks. Especially once we had kids, I was not that fond of the Parrotheads. 

It turns out, however, that Jimmy Buffett and Frank Taylor had something more in common, and I learned this only as I consumed the many remembrances of Buffet that were printed and aired after he passed away on Sept. 1. Both men traveled to Cuba long before official American proscriptions against general travel there were lifted in 2015.

Cuba has a complex history of colonization and instability. Its great wealth, with origins in the genocide of aboriginal inhabitants starting with Christopher Columbus, and subsequent sugar and coffee plantations with enslaved workers, seems to have encouraged internal corruption and external interventions. The Cuban Revolution, completed with the installation of Fidel Castro as leader in 1959, established a socialist government which nationalized most of the country’s resources. A rift with the United States followed, including an embargo on Cuban goods which damaged Cuba’s economy. Even when limited diplomatic relations were reestablished in the 1970s, Cuba remained in relative isolation and poverty. Most Cuban-Americans came here after their revolution, fleeing the socialization of their wealth and property at the beginning, and poverty, lack of national resources, and human rights concerns more recently. 

Cuba’s enforced isolation made it a pariah for some and an intriguing mystery to others. While Cuba did not open for official American tourism until 2016, Frank traveled to Cuba at some point towards the end of the 20th century. He apparently jumped on a yacht, with friends, and simply sailed the 90 miles south. The tale he told with piratical flair when they returned included attending an official dinner where President Castro delivered a grueling three-hour speech. 

Buffett, interestingly, went as early as 1983, to help with a documentary about Ernest Hemingway, another Key West author. He apparently returned regularly, performing for U.S.  citizens stationed there and also for, and with, Cuban musicians and audiences. I don’t know, but I imagine he might have also simply jumped on a boat for unofficial trips. 

What sits with me at this moment is that we humans generally embody a great deal of contradictions and complexity, though we often choose to celebrate the most superficial things. Beautiful islands, for example, attract all kinds of people seeking pleasure. But they often have depths of culture and diversity. Key West is a great example, but so is Newport, which was known for beer and beaches when I was in college in Massachusetts, but clearly was, and is, a much more complicated, and interesting place. 

The same is true of individual people. Jimmy Buffett had a reputation as a boozy sailor, bar bard of the rowdy tourist. But he was clearly more than that. Paul McCartney and Bob Dylan saluted his songwriting. His business acumen has been documented at great length over the past few weeks. By the end of his life, he was living a healthy lifestyle and enjoying the fruits of his success and great wealth. His trips to Cuba may have been in keeping with his pirate reputation, but they also demonstrate curiosity, generosity, and an open mind. 

A bit late, I find myself a fan. 


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Ruth S. Taylor
Ruth S. Taylor

Ruth S. Taylor retired at the end of 2022 after 16 years as executive director of the Newport Historical Society. She now serves as a consultant working to improve the governance of nonprofit organizations. She also serves as chair of the Rhode Island Historical Preservation & Heritage Commission.