Courtesy of Chris Whipple

On Thursday, the Jackson Institute for Global Affairs held a virtual discussion with journalist Chris Whipple ’75 on his new book, “The Spymasters: How the CIA Directors Shape History and the Future.”

Published on Sept. 15, “The Spymasters” details the roles that past and present Central Intelligence Agency directors have played in crises and turning points of history. Thursday’s Zoom event was moderated by Asha Rangappa LAW ’00, a former Federal Bureau of Investigation agent and Jackson Institute senior lecturer. During the discussion, Whipple answered questions and shared his thoughts on the current trajectory of the CIA, emphasizing the importance of the CIA director. 

“It is, at the end of the day, the CIA director’s responsibility to be the honest broker of intelligence, not only to the President, but to Congress and to the American people,” Whipple told the virtual audience.

In addition to giving historical assessments of the careers of past CIA directors, Whipple also described the current challenges faced by the CIA under the leadership of Gina Haspel, President Donald Trump’s appointee and the agency’s first female director.

Whipple explained the essential balance that CIA directors must strike between their role as an objective informer and their need to keep a positive personal relationship with the president. When the relationship between the CIA director and the president breaks down, the agency loses its credibility, and episodes of scandal and conflict like those detailed throughout “The Spymasters” abound. 

“[The CIA] has to balance on the one hand a certain amount of independence in coming up with its intelligence assessments, you know, so that they can be an objective input into the policy decision-making process,” said Rangappa. “But when that policy decision-making process is done, they must carry out those orders. And so, you know, the President is their consumer.”

Before the Zoom discussion, Whipple spoke to the students of GLBL 392: “Intelligence, Espionage and American Foreign Policy.” The course, taught by Jackson Institute lecturer Edward Wittenstein, assigned “The Spymasters” as part of a unit on human intelligence and covert action.

Joey Gagnard GRD ’21 at the Jackson Institute taking the course, spoke to the News about his impression of hearing Whipple talk about “The Spymasters” in class.

“He really drove home the personal aspect of the relationship between the commander-in-chief and the director of the CIA,” said Gagnard. “How these personalities can change strategic policy and the direction of a country. He just sort of broke it down in a really concise format that was easy for everyone to take in.”

“The Spymasters” follows Whipple’s work on a documentary that aired on Showtime in 2015 called “The Spymasters: CIA in the Crosshairs.”

In an interview with the News, Whipple explained why he returned to the subject of the CIA directors, which is the focus of his documentary. 

“The film just barely scratched the surface of this unbelievable, untold story of 17 men and one woman who have run the world’s most powerful intelligence agency,” Whipple said.

Rather than rely on archives, Whipple preferred to interview his principal subjects, a process that began in 2013. In both the documentary and the book, Whipple was granted interview access to almost every living CIA director, with the exceptions of Mike Pompeo and Haspel.

Whipple not only looks to the directors, but also their colleagues, friends, families, the Department of Defense and the White House.

“I hope the book succeeds in humanizing these mysterious people,” Whipple said.

Whipple recalled talking to Cynthia Helms about her late husband Richard Helms, who Whipple described to the News as “the quintessential CIA director, old-school, martini in one hand, cigarette in the other.” Richard Helms would come home from work and tell Cynthia that he had lash marks on his back from then-Attorney General Bobby Kennedy hectoring him to get rid of Fidel Castro “by fair means or foul,” Whipple added. Helms served as director from 1966 to 1973.

In another anecdote from “The Spymasters,” former Director Leon Panetta — who served from 2009 to 2011 — fingers his rosary beads and says Hail Marys while deciding whether to authorize a lethal drone strike on a terrorist in Pakistan, when he knows it may endanger innocent civilians.

“It’s not for the faint of heart,” Whipple told the News. “If you want to sleep well, don’t apply for the job of CIA Director.”

“The Spymasters” is Whipple’s second book, following his 2017 examination of White House chiefs of staff in the New York Times bestseller “The Gatekeepers.”

Margot Lee |

Sylvan Lebrun |

Sylvan Lebrun reports on City Hall. She previously covered nonprofits and social services in the New Haven area. She is a sophomore in Pauli Murray College majoring in English.