I Sat 'Between Two Roosevelts' for a Rousing Political Debate

Putting 2 dead US presidents + 1 presidential candidate in front of a mic to debate modern political policy sounds like the setup for a strange joke.

It isn’t—well, okay, maybe a little bit — but beneath the absurd premise lies an important political thought experiment.

In the premiere of Between Two Roosevelts, which you can watch at the top of this post, we’ve paired satire with genuine political debate, proving that while Theodore Roosevelt and Franklin D. Roosevelt may be long gone, the issues they fought for are painfully alive today.

The Roosevelt Debates 2026

Here are some more highlights:

* Corporate Monopolies: Theodore Roosevelt (played by Josh Weinstein) notes that today’s corporate landscape mirrors the trusts of his era, arguing that government must act as a referee to protect consumers and workers.

* Systemic Disadvantages: Franklin Roosevelt (played by Brent Forrester) agrees on checking corporate power, but pushes further by arguing government must actively support those at the bottom of the economic pyramid so citizens don’t end up on the breadline.

* Government Overreach: Teddy warns against replacing corporate dominance with state overreach, cautioning against a “nanny state.” He also cites his creation of the Department of Commerce and Department of Labor as the proper model for protecting workers while giving fair businesses a square deal.

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CAMPAIGN BUTTON DESIGN WINNER:

We recently held our first Dan Greaney USA design competition to see what button designs our talented community could dream up. We got a lot of fun submissions.

We’re happy to unveil the winner: Ryan Castellano, one of our valued volunteers.

Using inspiration from some old-timey political imagery (below), including a few shared with Dan by fellow volunteer Josh Weinstein, the winning design that Ryan submitted will be printed as an actual campaign button.

We will share more of the submissions in an upcoming post (and even announce new fun competitions) so be sure to subscribe to @dangreaneyusa here and on social media.

PS - Did you know you can join Team Dan Greaney as a volunteer?

Head over to the campaign website to see the ways you can help us create an America For All.