In this episode of The Rest Is History, we dive into the chaotic 1968 Democratic National Convention in Chicago. The conversation highlights the intense showdown between the traditional Democratic Party, led by Mayor Richard J. Daley and Hubert Humphrey, and the rising counterculture movement represented by the Yippies (Youth International Party) and the MOBE (National Mobilization Committee to End the War in Vietnam). Spearheaded by Abbie Hoffman and Jerry Rubin, the Yippies used theatrical protests and bold actions to challenge both the Vietnam War and the Democratic establishment. Their confrontational approach, combined with an already charged political atmosphere and the Chicago police's harsh tactics, sparked violent clashes and widespread riots. This turmoil not only tarnished the Democratic Party's reputation but also played a significant role in Humphrey's defeat in the presidential election.