The Lawfare Podcast

Lawfare Archive: The Spymasters with Chris Whipple

Apr 26, 2025

Chris Whipple, a renowned documentary filmmaker and author of "The Spymasters" and "The Gatekeepers," explores the intricate dynamics between CIA directors and the presidency. He discusses ethical dilemmas faced by directors during crises and the impact of their decisions on national security. Whipple highlights the evolution of the CIA post-Cold War, controversial interrogation techniques, and the delicate balance of diplomacy in intelligence. He also reflects on former directors publicly criticizing presidents and the implications this has for the intelligence community.

52:02

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Episode guests

Chris Whipple

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Quick takeaways

CIA directors must balance loyalty to the President with their responsibility to provide unbiased intelligence, especially during crises.

The shift towards transparency in the intelligence community, initiated by directors like Bill Colby, significantly altered oversight dynamics and governmental relations.

Deep dives

The Relationship Between CIA Directors and the Presidency

The dynamic between CIA directors and the President is crucial for effective governance. The conversation highlights the expectations of CIA directors in balancing loyalty to the President while also adhering to their mandate of providing unbiased intelligence. Historical cases, such as those involving directors like Dick Helms, illustrate the tension directors face when asked to execute arguably illegal orders. This relationship impacts not only the functionality of the CIA but also national security decisions, emphasizing the role of the director as an honest broker of information during times of crisis.

Intro

3min

The CIA Director's Dilemma

23min

Shifting Paradigms: The CIA's Evolution After the Cold War

4min

Leadership Challenges and Missteps of CIA Directors

2min

Complexities of CIA Interrogation Techniques

14min

Diplomacy in Intelligence: A Delicate Balance

8min

Exploring CIA Directors' Relations with Presidents

2min

From September 16, 2020: What is the proper relationship between the CIA director and the president? How should directors handle arguably illegal orders? How important is the director's role as the nation's honest broker of information during times of crisis?

To get at these questions, David Priess sat down with Chris Whipple, a documentary filmmaker, journalist and the author of two books about the people around the president. "The Gatekeepers," based upon his documentary of the same name, examines White House chiefs of staff, and his new book, "The Spymasters: How the CIA Directors Shape History and the Future," is based on the Showtime documentary "The Spymasters: CIA in the Crosshairs," for which Whipple was the writer and executive producer. They talked about CIA directors through the last several decades and how they've impacted U.S. history and national security.

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