The Spymasters

1. CIA Directors Navigate a Political Minefield

The job of CIA director is as difficult as it is important.

High-stakes role. The CIA directorship is a critical but precarious position, second only to the commander-in-chief in consequence. Directors serve as the president's eyes and ears, providing intelligence that shapes decisions ranging from averting global catastrophes to starting unnecessary wars.

Political pressures. Directors must balance their duty to provide objective intelligence with the political realities of serving a president. This tension can lead to ethical compromises, as presidents often seek to use the CIA for their own agendas, creating false reasons for war or covering up scandals.

Historical examples. The book highlights numerous examples of directors who succeeded or failed based on their ability to navigate this political landscape. Some, like Richard Helms, upheld the rule of law, while others, like William Casey, broke the law and nearly destroyed the agency.

2. Helms: Loyalty Tested by Presidential Demands

They were all asked to do things they shouldn’t do.

Helms's balancing act. Richard Helms, a career CIA officer, faced numerous ethical dilemmas during his tenure, particularly under Presidents Johnson and Nixon. He often found himself caught between his duty to the law and his loyalty to the president.

MHCHAOS and Watergate. Helms reluctantly approved Operation MHCHAOS, an illegal domestic surveillance program, to appease Johnson's paranoia about the anti-war movement. However, he defied Nixon's attempts to obstruct justice in the Watergate scandal, protecting the CIA from being used as a political tool.

Character and compromise. Helms's willingness to bend the law for Johnson but not for Nixon raises questions about the role of personality and character in ethical decision-making. It also underscores the difficulty of maintaining a consistent moral compass in the murky world of intelligence.

3. Schlesinger and Colby: Reformers Meet Resistance

No alien penetration or treachery of double agents has ever done nearly as much damage to the CIA as the infighting consequent upon the arrival of each new director.

Outsider challenges. James Schlesinger and William Colby, both appointed to reform the CIA, faced significant resistance from within the agency. Schlesinger's abrasive style and mass firings alienated the workforce, while Colby's transparency efforts exposed the agency's darkest secrets.

Schlesinger's unpopularity. Schlesinger's mandate to cut costs and eliminate "deadwood" led to the termination of over a thousand veteran operatives, creating deep resentment and undermining morale. His intellectual arrogance and lack of understanding of the agency's culture further fueled his unpopularity.

Colby's transparency. Colby's decision to reveal the "Family Jewels," a compendium of CIA abuses, was intended to save the agency by acknowledging its past mistakes. However, it triggered a wave of congressional investigations and media scrutiny, further damaging the CIA's reputation.

4. George H.W. Bush: Restoring Agency Morale

The CIA has one protector and one customer, and if you can’t get that relationship right then the agency is screwed.

Bush's unique position. George H.W. Bush, a former envoy to China with no prior intelligence experience, was initially seen as an unlikely choice to lead the CIA. However, he proved to be a skilled leader who restored the agency's morale and reputation after a period of scandal.

Political acumen. Bush's political savvy and ability to navigate the corridors of power in Washington, D.C., allowed him to protect the CIA from further attacks and secure its funding. He also fostered a sense of camaraderie and respect within the agency, earning the trust of both analysts and operatives.

Setting the stage. By rescuing the agency from scandal and restoring its reputation, Bush set the stage for his own political career, eventually becoming president of the United States. His tenure as CIA director demonstrated the importance of leadership, integrity, and political skill in guiding the agency through turbulent times.

5. Turner and Intelligence Failures: Iran as a Case Study

As a country we just don’t have good intelligence.

Turner's missteps. Admiral Stansfield Turner, appointed by Jimmy Carter, was an earnest but straitlaced leader who struggled to adapt to the rough-and-tumble world of espionage. His lack of political finesse and his focus on technology over human intelligence contributed to one of the agency's greatest intelligence failures: the Iranian Revolution.

The Iranian Revolution. The CIA's failure to anticipate the 1979 Iranian Revolution, which toppled the U.S.-backed Shah, was a seismic shock that triggered a struggle between the West and militant Islam. The agency's lack of understanding of Iranian culture, religion, and politics contributed to its inability to foresee the uprising.

Lessons learned. The Iranian Revolution highlighted the importance of cultural awareness, language skills, and human intelligence in gathering accurate information. It also underscored the dangers of relying solely on technology and neglecting the human element of espionage.

6. Casey's Covert Wars and Ethical Lapses

The CIA has one protector and one customer, and if you can’t get that relationship right then the agency is screwed.

Casey's power and ambition. William Casey, appointed by Ronald Reagan, was a powerful and ambitious director who waged covert wars against the Soviets and their proxies around the globe. He armed the mujahideen in Afghanistan, helping to turn the tide against the Soviet Red Army.

Iran-Contra scandal. However, Casey's zeal to fight communism led him to break the law in the Iran-contra scandal, trading arms to Iran for hostages and illegally diverting profits to the contras in Nicaragua. This scandal nearly destroyed the Reagan presidency and tarnished the CIA's reputation.

Ethical boundaries. Casey's actions serve as a cautionary tale about the dangers of unchecked power and the importance of ethical boundaries in intelligence operations. His story underscores the need for congressional oversight and accountability to prevent future abuses.

7. Webster: Integrity After Scandal

Stay the hell away from the whole damned thing.

Webster's mission. William Webster, a former FBI director and federal judge, was appointed to restore integrity and credibility to the CIA after the Iran-contra scandal. He was seen as a squeaky-clean figure who could reassure Congress and the American people that the agency was committed to the rule of law.

Restoring trust. Webster's emphasis on ethics and accountability helped to rebuild trust in the CIA. He implemented reforms to prevent future abuses and worked to improve the agency's relationship with Congress.

Navigating a changing world. Webster also faced the challenge of adapting the CIA to a post-Cold War world. He oversaw the agency's transition from a focus on the Soviet Union to new threats such as terrorism, drug trafficking, and nuclear proliferation.

8. Gates: From Analyst to Director Amidst Soviet Collapse

There are only policy successes—and intelligence failures.

Gates's expertise. Robert Gates, a career CIA analyst, brought deep knowledge of the agency and its operations to the directorship. He helped President George H.W. Bush navigate the dangerous shoals of the post-Cold War world after the collapse of the Soviet Union.

Navigating the transition. Gates faced the challenge of reorienting the CIA from its focus on the Soviet Union to new threats such as terrorism, drug trafficking, and nuclear proliferation. He also had to manage budget cuts and personnel reductions as the agency adapted to a new era.

The Ames betrayal. Gates's tenure was marred by the discovery of Aldrich Ames, a CIA officer who had been spying for the Soviets for nearly a decade. Ames's betrayal led to the execution of numerous CIA assets and caused significant damage to U.S. intelligence operations.

9. Woolsey and Deutch: Adapting to a Post-Cold War World

At CIA you get into moral ambiguities more than you do in other agencies.

New challenges. James Woolsey and John Deutch, who served as CIA directors under President Bill Clinton, faced the challenge of adapting the agency to a post-Cold War world. They grappled with new threats such as terrorism, cyber warfare, and ethnic conflicts.

Woolsey's struggles. Woolsey struggled to connect with Clinton and was seen as out of touch with the agency's culture. His tenure was marked by the Ames scandal and a series of other intelligence failures.

Deutch's vision. Deutch was a brilliant technocrat who helped usher in the era of unmanned drone warfare. However, he was politically tone-deaf and made several missteps that undermined his authority.

10. Tenet: 9/11 and the Iraq WMD Debacle

It’s not enough to ring the bell; you have to make sure the other guy hears it.

Tenet's warning. George Tenet, who served as CIA director under both President Clinton and President George W. Bush, warned of an imminent Al Qaeda attack in the summer of 2001, months before 9/11. However, his warning went unheeded by the Bush administration.

The Iraq War. Tenet's legacy was marred by the controversy over Iraq's weapons of mass destruction. His assurance to President Bush that the case for Saddam Hussein's WMDs was a "slam dunk" helped to spur the invasion of Iraq in 2003.

A complex legacy. Tenet's tenure was a mix of successes and failures. He launched the CIA's lightning invasion of Afghanistan, routing the Taliban. But his legacy will forever be tarnished by the controversy over enhanced interrogation techniques and the faulty intelligence on Iraq's WMDs.

11. Post-9/11: The Ethical Quagmire of Counterterrorism

At CIA you get into moral ambiguities more than you do in other agencies.

Enhanced interrogation techniques. In the aftermath of 9/11, the CIA implemented a program of enhanced interrogation techniques (EITs) that were widely condemned as torture. The program sparked a debate about the ethical limits of intelligence gathering and the balance between national security and human rights.

The drone program. The CIA's use of lethal drones to target suspected terrorists also raised ethical and legal questions. While drones were seen as a precise and effective tool for eliminating threats, they also raised concerns about civilian casualties and the lack of transparency and accountability.

The whistleblower. In January of 2020, a complaint brought by a CIA whistleblower resulted in a Senate trial of Donald Trump for high crimes and misdemeanors. It is up to CIA director Haspel—and the acting Director of National Intelligence, her nominal superior—to protect that whistleblower from reprisal.

12. Haspel: Navigating Trump's Distrust and a Divided Agency

CIA directors and deputies make some of the toughest decisions in government.

Haspel's challenges. Gina Haspel, the first woman to become CIA director, faced the challenge of leading the agency during a time of political polarization and distrust of the intelligence community. She had to navigate President Trump's skepticism toward the CIA and his admiration for Vladimir Putin.

The Khashoggi murder. Haspel was thrust into the middle of a scandal involving the murder of Saudi journalist Jamal Khashoggi. She had to balance the need to hold Saudi Arabia accountable for the crime with the strategic importance of the U.S.-Saudi relationship.

Protecting the whistleblower. On her watch a CIA whistleblower would plunge her into the middle of a scandal involving Ukraine and Trump that would trigger his impeachment. It is up to CIA director Haspel—and the acting Director of National Intelligence, her nominal superior—to protect that whistleblower from reprisal.

Last updated: February 24, 2025