The Gadiel Del Orbe Show

From Navy Republican to Trans Democratic Socialist: Josie Caballero’s Journey

Episode Summary

In this episode, Gadiel sits down with Josie Caballero — a trans Latina Navy veteran and democratic socialist running for Montgomery County Council At-Large in Maryland. They dive into what American socialism really means, why capitalism in the U.S. feels so broken, how the housing crisis and private equity are squeezing everyday people, and why ICE’s tactics look more and more like an authoritarian police force. Josie also shares how she went from a hardcore Republican in the military to a democratic socialist candidate, breaks down socialism vs. communism vs. capitalism in plain language, and lays out her platform: Locking in funding for public education Strong rent control to protect tenants Holding ICE accountable when it breaks the law If you’ve ever felt politically homeless, confused about “socialism,” or worried about where America is headed, this conversation will give you a lot to think about.

Episode Notes

Guest:

Josie Caballero – Trans Latina Navy veteran and democratic socialist running for Montgomery County Council At-Large (MD)

In this episode we talk about:

How Josie and Gadiel met in the Navy and why she feels like family

What it’s like running for office as a trans woman in such a divisive moment

Why terms like socialism, communism, and capitalism are so misunderstood

“American socialism” explained through Medicare, VA benefits, public schools, roads, firefighters, and Social Security

How we got from FDR and the New Deal to today’s corporate-driven economy

The Dunning-Kruger effect and why so many people are confident but wrong about politics

Josie’s turning point: from conservative Republican to democratic socialist

Why the housing crisis exists (private equity, “luxury” buildings, and fake “affordable” units)

How rent control, public housing, and better building standards could actually fix it

ICE, raids, and why Josie says we’re already edging into an authoritarian state

What due process really means — and why it matters for citizens and immigrants

Josie’s policy priorities:

52% of the county operating budget guaranteed for schools

3% rent cap with no loopholes

Enforcing the law against ICE when it breaks it

Support Josie’s campaign:

Website: joseformaryland.com

Connect & Join the Conversation:

Tell us what you agreed with, what you disagreed with, and what you’re still confused about.

Leave a comment or DM Gadiel with your thoughts and questions for a future follow-up episode.