In Episode 118, Garrett sits down with Tampa City Councilman Alan Clendenin for a wide-ranging and brutally honest conversation about the future of Tampa. They dive into the state of public transportation, including the controversial streetcar expansion and how to better connect downtown to the airport. Clendenin shares what’s really holding back progress—from permitting delays to the tangled web of city, county, and state control. They also explore the city’s approach to development, land use reform, housing affordability, and the urgent need for better infrastructure. With decades of experience and no political strings attached, Clendenin offers a rare look into how big decisions are made—and what’s at stake if Tampa gets them wrong.

0:02:15 - Tampa's transportation system needs a bold vision

0:13:40 - Streetcar expansion revival and challenges

0:22:18 - Why Tampa’s ferry system is a missed opportunity

0:31:12 - The truth about tree canopy laws and development

0:45:00 - Tampa's overcrowding and infrastructure strain

0:53:00 - Why the city needs control over major roads

1:00:15 - The $500M mistake: expanding 275

1:04:35 - The politics of streetcar funding and fare-free transit

1:18:10 - Why planned developments (PDs) are being misused

1:39:00 - The unsung heroes shaping Tampa’s future