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October 5, 2025 15 mins

This week on The Deep Dive, we’re unpacking one of the strangest cultural collisions of the year — the moment Florida’s First Lady Casey DeSantis asked the internet who Bad Bunny is… and the internet exploded.

The backdrop? Bad Bunny being named the Super Bowl 60 halftime headliner — a move that thrilled fans but set off political fireworks. Within hours, conservative voices labeled him everything from a “Trump hater” to an “anti-ICE activist,” while millions of Floridians reminded the First Lady that the reggaeton superstar is, well, one of the most-streamed artists on the planet.

We break down:

  • Why Bad Bunny’s music is more than beats — it’s cultural power and political statement.

  • How one post on X triggered an online identity crisis about what “Florida culture” even means.

  • The bigger implications of Latino and Spanish-language artists redefining mainstream America.

  • And what it says when leaders claim not to know the most popular artist in their own backyard.

From Puerto Rico to politics, fandom to Florida — this episode is part pop culture, part sociology, and all chaos.

If you ever want to buy or sell a property anywhere in the world, our team would be honored to help get you to your next destination.

Until next time, stay curious, stay hungry, and as always… stay ALL IN!

Amit Bhuta COMPASS ALL IN Miami Group Licensed Real Estate Agent

(305) 439-3031 Mobile amit.bhuta@compass.com ALLinMiami.com

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