Day 2: Pirates of St Augustine

St Augustine is the second oldest European-established settlement in the USA. It was founded in 1565 by the Spanish, repeatedly plundered by pirates (Sir Francis Drake, Robert Searle), a haven for the British loyalists during the American Revolutionary War and joined the Confederates during the American Civil War. Henry Flagler built a lot of prominent buildings in St Augustine as he expanded his Florida East Coast Railway, southwards to Palm Beach and Miami. St Augustine is also renowned for arresting Martin Luther King, Jr. and violent responses by the KKK and Police to peaceful civil rights protests to end segregation. Even today it maintains a strong Republican/MAGA leaning with 60%+ voting for Republica candidates for the 2016 and 2020 elections. It has a history steeped in violence and conquest – in the name of god, gold or ideology.

As we took a guided tour of the city, taking in the old architecture, landmarks and stories from its history, I couldn’t help but notice two things. Firstly when it came to defining moments in history, the inhabitants of St Augustine seemed to have chosen to maintain the status-quo and ended up on the wrong side of history. Three examples are the American Revolutionary War, the American Civil War and the American Civil Rights movement.

The second thing I noticed was that despite so many firsts in the USA (the first continuous European settlement, first Catholic Mass in the USA and first peace treaty “thanksgiving” with the native inhabitants) as well as money poured into the city (Henry Flagler), St Augustine never grew as prosperous as other cities in Florida such as Miami or Fort Lauderdale.

I wonder if the first has something to do with the second. A staunchly conservative approach might have kept people, migrants, innovators and businesses away from St Augustine. St Augustine has a much smaller population and is certainly not as diverse or progressive as the cities of Fort Lauderdale and Miami.

The other reason might have been the dominance of Flagler during key moments. The stories shared by the tour guide highlighted Flaglar’s insistence on certain rules and aggressively defeating his opponents. It almost looks like his wealth and prominence eliminated any competition. Once the competition was eliminated, St Augustine’s economic viability was left to the mercy of a single wealthy benefactor. It was Flaglar’s way or no investment or gifts for the city. Leaving me to wonder if this is similar to other wealthy individuals who have built a town or community around them such as Sam Walton (Bentonville, AK), Jeff Bezos (Seattle, WA) and Bill Gates (Bellevue, WA).

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