In this episode of the LCI Greenroom, Jacob Winograd hosts Austin Padgett for a deep dive into the ongoing coalition efforts between libertarians and the MAGA/MAHA movements. They explore the tension between staying principled and pursuing political pragmatism, particularly in the context of supporting Donald Trump as a strategic move. The discussion covers the emotional and philosophical struggles libertarians face when assessing Trump's performance, especially regarding issues like foreign policy toward Ukraine and Israel, regulatory rollbacks, and the freeing of Ross Ulbricht. Jacob expresses cautious regret over his vote for Trump while acknowledging tangible libertarian wins, while Austin emphasizes patience, strategy, and the complexity of achieving deregulation and decentralization through current political realities.

The conversation also addresses broader philosophical concerns, including how libertarians should engage coalitions without losing their identity, how to respond to foreign aid and interventionism (especially concerning Israel and Palestine), and the importance of maintaining pressure on political figures while navigating the balance between support and critique. They further touch on sensitive topics like immigration enforcement, the danger of compromising core libertarian values in coalition politics, and the importance of focusing on long-term structural reforms—such as deregulation and decentralization—over short-term emotional reactions. Throughout, Austin advocates for a strategic optimism about leveraging the present political moment, while Jacob urges caution against losing sight of fundamental libertarian principles.

In this episode, Jacob is joined by Jeremiah Harding for an unfiltered conversation about Donald Trump's alarming shift toward authoritarianism. They discuss how Trump's record on war, foreign policy, surveillance, and civil liberties has deeply betrayed the liberty movement. Both reflect on the false promises of Trump’s outsider image, the reality of his policies, and how many libertarians, including Jacob himself, feel growing regret over supporting him. They explore how issues like immigration, militarization, and coalition-building have been weaponized in ways that libertarians and Christians must not ignore.

This is the first of a two-part series. In the next episode, Jacob will be joined by a guest offering a more sympathetic view of Trump's presidency, providing a balanced discussion about how liberty-minded individuals can and should engage with the difficult realities of modern politics. Stay tuned for a respectful but challenging follow-up conversation!

In this live conversation, Jacob is joined by Martha Bueno — a Cuban-American libertarian activist, communicator, and former Vice Chair of the Libertarian Party of Miami-Dade — for a deep and wide-ranging discussion on how we can actually advance liberty in our culture, our politics, and our homes.

We’ll reflect on the incredible moment earlier this year when Ross Ulbricht was finally freed, and what that victory means for the future of digital freedom, justice, and the limits of state power.

Martha brings a unique perspective as a first-generation American, small business owner, and international advocate for liberty — especially in Latin America. We’ll explore how her approach to peaceful parenting, local political action, and public communication can help build a more vibrant, sustainable liberty movement.

We’ll also wrestle with the tensions between principle and pragmatism in libertarian circles — and how we can overcome division and chart a course forward that brings real change, without compromising our values.

Whether you’re new to the ideas of liberty or a seasoned activist, this conversation will inspire you to live free, parent intentionally, and work toward a more peaceful and voluntary society.