Jack Goldsmith on Jimmy Hoffa, labor unions, and the rise and fall of the mob

Goldsmith discusses his personal experience with the most famous disappearance in American history. Click "Show more" to view all chapters. For more conversations, visit

Chapter 1 (0:15 - 22:30): A Stepfather and the Hoffa Case

Chapter 2 (22:30- 58:54): On Hoffa, Unions, and the Mob

Jack Goldsmith is a professor of law at Harvard, an expert on national security, terrorism, and cybersecurity—and a regular guest on Conversations. As he reveals in a fascinating new book, "In Hoffa’s Shadow," from the age of 12 in 1975 he was personally wrapped up in one of the most contentious episodes in American history—the disappearance of the powerful Teamsters Union boss Jimmy Hoffa. In this Conversation, Goldsmith recounts how his stepfather, Charles “Chuckie” O’Brien, became the prime suspect in Hoffa’s disappearance, and how this affected their relationship over the next decades. Goldsmith then shares his own research into the Hoffa case and what he learned along the way about his stepfather, the life and career of Jimmy Hoffa, the history of labor unions in the United States, and the rise and fall of the mob. This is a deeply personal, moving Conversation that has much to teach us about the complexities of family, law, and politics.