$55 million just changed hands between two Chicago investment families, but the action wasn’t in the Windy City—it was on the waterfront in Naples’ Port Royal. John Southard, fresh off a $2 billion ETF deal with Goldman Sachs, bought a six-bedroom mansion from Collin Roche’s family, both with deep Chicago ties. This isn’t just a flashy real estate move; it’s a sign of how Chicago’s financial heavyweights are snapping up trophy homes in Florida’s most exclusive enclaves. What do you think—smart investment, lifestyle upgrade, or both? #RealEstate #ChicagoMoney #NaplesRealEstate