Chris Matthews Reveals Untold Stories from Washington’s Back Rooms

In this wide-ranging episode, American political commentator, retired talk-show host, and author Chris Matthews joins Gentry to discuss his new book, Lessons from Bobby: Ten Reasons Robert F. Kennedy Still Matters. Matthews lays out why RFK’s moral courage, coalition-building, and willingness to risk political capital still resonate—and what those lessons mean for the country now.

Grab the book here: Buy Lessons from Bobby. Simon & Schuster

Beyond the book, Chris shares a remarkable story from his younger years hitchhiking across Africa, then pivots to an unflinching conversation about the Kennedy legacy—with a special focus on Bobby. He and Gentry also unpack today’s political flashpoints: the new New York mayor and Assembly member Zohran Mamdani, the evolving crises between the U.S., Israel, and Palestine, and the brutal realities of the Russia–Ukraine war.

It’s candid, timely, and steeped in history—an essential listen for anyone who cares about American politics and the ideas that still shape it.