What happens when a musician sails into Key West, finds a stage within 48 hours, and spends the next four decades turning island life into melody and memory? We sit down with Ben Harrison—singer, author, playwright, and local historian—to uncover how music and baseball braided together to shape Key West culture, pride, and identity.

Ben takes us back to late-afternoon sets at the Pier House and long runs at the Bull on Duval Street, then forward to intimate nights in the Key West Theater’s backstage listening room. Along the way, he shares why Elvis cracked his world open, how a Shel Silverstein cover sneaks into his set, and what separates a sturdy song from a good book chapter. The stories are pure Conch: roaming roosters, sirens by Flagler, and a community that always seems to show up when it counts.

The heart of our talk digs into Ben’s new book on the history of Key West baseball. He traces the game’s roots to the 1800s, carried by soldiers and nurtured by a deep connection with Cuba. We explore the 1950s golden era of Key West High School championships, the brief polio pause that sidelined a season, and the small-ball savvy borrowed from Havana’s winter leagues. We honor the Negro Leagues and the Key West Coconuts, noting how segregation hid greatness in the archives while talent kept winning on the field. Hustle, more than anything, emerges as the island’s competitive edge.

Community runs through it all. Ben serves on the Bahama Village Music Program board, a free, all-instruments effort that pairs kids with teachers, turns seniors into mentors, and sends standouts to Berklee each summer. It’s proof that access fuels skill, and skill builds the confidence that keeps culture alive. We close on what success really means: choosing happiness, doing the work you love, and raising a family proud to call themselves Conchs.

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