Uploaded February 2026 | Updated September 2026, 1 day ago
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I recently sat down with Maya Rupert for a conversation that moves beyond labels and talking points.
Maya and I have appeared together on MSNOW, and I’ve always appreciated our exchanges. We don’t agree on everything, but we’re able to talk through differences with respect and even a little humor, something that feels far too rare in politics today.
Maya is an attorney, former presidential campaign manager, and national political strategist. She earned her B.A. from UC Santa Barbara, her law degree from UC Berkeley, clerked on the Sixth Circuit Court of Appeals, and now serves on the board of the National Women’s Law Center. She also writes the Substack newsletter Power Breakers and hosts the podcast When We Win.
In our conversation, we dig into what the Democratic agenda should look like, how to speak to voters who feel left behind, and whether urgency can be matched with unity. Even when we disagreed, the focus stayed on strengthening the country.
That kind of civil exchange used to be normal. Today, it feels necessary.
Join my free substack newsletter for more! johnkasich.substack.com
I recently sat down with Maya Rupert for a conversation that moves beyond labels and talking points.
Maya and I have appeared together on MSNOW, and I’ve always appreciated our exchanges. We don’t agree on everything, but we’re able to talk through differences with respect and even a little humor, something that feels far too rare in politics today.
Maya is an attorney, former presidential campaign manager, and national political strategist. She earned her B.A. from UC Santa Barbara, her law degree from UC Berkeley, clerked on the Sixth Circuit Court of Appeals, and now serves on the board of the National Women’s Law Center. She also writes the Substack newsletter Power Breakers and hosts the podcast When We Win.
In our conversation, we dig into what the Democratic agenda should look like, how to speak to voters who feel left behind, and whether urgency can be matched with unity. Even when we disagreed, the focus stayed on strengthening the country.
That kind of civil exchange used to be normal. Today, it feels necessary.
