The Spymasters: How the CIA Directors Shape History and the Future

by Chris Whipple

From the New York Times bestselling author of The Gatekeepers, a remarkable, behind-the-scenes look at what it’s like to run the world’s most powerful intelligence agency—the CIA—as well as a sobering glimpse at the espionage and surveillance challenges of the future.

Only fourteen men and one woman are alive today who have made the life-and-death decisions that come with running the world’s most powerful and influential intelligence service. With unprecedented, deep access to all these individuals, Chris Whipple tells the story of an agency that answers to the United States president alone, but whose activities—spying, espionage, and covert action—take place on every continent.

Since its inception in 1947, the Central Intelligence Agency has been a powerful player on the world stage, operating largely in the shadows to protect American interests. For The Spymasters, Whipple conducted extensive, exclusive interviews with nearly every living CIA director, pulling back the curtain on the world’s elite spy agencies and showing how the CIA partners—or clashes—with counterparts in Britain, France, Germany, Israel, Jordan, Saudi Arabia, and Russia. He covers every topic from the influence of the White House on intelligence activity to simmering problems in the Middle East and Asia to rogue nuclear threats and cyberwarfare.

A revelatory look at the CIA’s impact across the globe, The Spymasters uncovers the inside stories behind the CIA’s seven decades of activity and elicits predictions about which issues—and threats—will occupy the espionage and surveillance landscape of the future. Including eye-opening interviews with George Tenet, John Brennan, Leon Panetta, and David Patraeus, as well as those who’ve just recently departed the Agency, this is a timely, essential, and important contribution to current events.

Genres: History, Nonfiction, Politics, Espionage, Biography, American History, Audiobook

400 pages, Hardcover

First published September 15, 2020

About the author

WHIPPLE is an acclaimed writer, journalist, documentary filmmaker, and speaker. A multiple Peabody and Emmy Award-winning producer at CBS’s 60 Minutes and ABC’s Primetime, he is the chief executive officer of CCWHIP Productions. Most recently, he was the executive producer and writer of Showtime’s The Spymasters: CIA in the Crosshairs.

Reviews

[Alexander Peterhans · Rating 4 out of 5]

A comprehensive and well researched overview of the different eras of the CIA, focusing on the relationship between presidents and agency directors.

The book gives a conflicting impression of the CIA. On one side we see an agency consisting of dedicated men and women, who form a stable base, and on the other side we see how important the working (and sometimes personal) relation is between the president and the director, how fragile that relation can be and how large its effect can be on the functioning of the agency - often to a frightening degree.

That said, some of the most interesting (and funniest, and most shocking) parts are exactly on that central relationship, the motherlode of course being in the final chapter on president Trump.

Although it's a hefty volume, the book can't go too deep on any one subject, but it's a great starting point for anyone interested in espionage and US politics.

(Kindly received an ARC from Simon & Schuster through Edelweiss)

[John McDonald · Rating 5 out of 5]

This is not a book about Donald Trump, but the reader cannot help but draw certain conclusions that the history of the leaders of US Intelligence service presented by the author, Chris Whipple, was designed to show the danger of Donald Trump's Presidency and how he has placed our military and civilian institutions at great risk.

At the conclusion of this very well written account of the role of the intelligence services, especially the CIA, and those who led the service over the days when Wild Bill Donovan essentially created the outfit out of the remnants of the US covert operations and intelligence gathering activities during WWII, author Chris Whipple, without saying so, lays out the evidentiary case why Donald Trump from the first day of his Presidency embarked on a mission to destroy the US intelligence services: he did not want to hear the truth or the evidence and [pause because this is very hard to write] Trump is an asset of Russian intelligence and puppet of Vladimir Putin.

You have to read the entire book to understand why the evidence Whipple presents makes Trump a traitor and not a traitor acting in America's cause. I will not attempt to replicate what he says, but the evidence is damning. Why would Trump be so intent on destroying the integrity and activity of US intelligence services? Every single President, liberal and conservative, has relied on intelligence gathering and covert activities not only to implement a credible foreign policy but ensure that human rights and democracy are protected across international frontiers.

Trump is a different story, though. He, first, is mentally and emotionally unable to correct his false impressions of the world and people. Further, he has special interests he seeks to protect through his Presidency and the resources available to it. Trump, according to the author, refuses to read, cannot be briefed orally because he has no attention span nor the focus required to sit and listen for more than a few minutes, and when the CIA decided the Presidential Daily Brief (the PDB)
should be presented by a video presentation with scenes and footage of the film, Trump was unable to sit through this medium of presentation.

The author makes what may be the most salient point stated in the entire book. He says, correctly I believe, that the Intelligence Services--CIA, Defense Intelligence, the SIGINT arm of intelligence at the National Security Agency, and even the Director of National Intelligence--has one and only one customer and one and only one protector, the President of the United States. When this point is fully understood, it becomes clear why Trump's undermining of the CIA and other Intelligence Services, even now after he was defeated in his reelection effort, is so devastating to our national security. If the President ignores, disparages, or otherwise undermines the work of these agencies and operators, national security is at risk. A President who fails to read, understand, and grapple with the security issues raised by intelligence information has foregone the most important aspect of his job duties as President. It should never be forgotten that the attacks of 9/11 in likely could have been avoided had George Bush and his advisors been more attentive to what the Middle East section analysts at the CIA were reporting, reporting which found its way into PDB.

A couple of Directors stand out for their candor and their attention to the moral compass they brought to the office. John Brennan and Leon Panetta are memorable as is Bob Gates, an IU Masters student when I was a freshman at IU in 1965 when Gates was the residence hall graduate counselor in Elliott Hall at Wright Quadrangle. I knew Gates only from working in the cafeteria and speaking to him when he came through the food line. Even then in 1965, 55 years ago, I remembered Gates as he assumed very prominent positions in the 2 Bush and Obama administrations. It struck me in those student days how taciturn, serious, and organized he was even as he managed the Elliot Hall bicycle team in IU's Little 500.

Even though there were notable failures over the years, it is impressive to me that each of the Director and other intelligence agency chiefs was not only smart but governed by an ethical and moral code that allowed them to resist most political pressure and stand up to their customer, the President. Only 1 really struck me as out of his element, and that was George Tenet, who essentially allowed the intelligence information to be obscured so that G.W. Bush and Cheney could wage war in Iraq in 1993. George Tenet, a huge Georgetown basketball fan, told Bush that Iraq was a "slam dunk." To this day, Colin Powell, a straight arrow and moral man, says it was the greatest mistake of his life to be persuaded by Tenet.

Summing up, the author states what a disingenuous, disinterested President can do. Trump, he writes, is a "human wrecking ball, shattering norms." And, we are the worse for it.

[HR-ML · Rating 4 out of 5]

Chris Whipple (CW) examined the modern era CIA
Directors and some controversies R/T the CIA. He
mentioned personalities of the Directors, independ-
ent thinkers VS those who were in lock-step with
the President they served.

CW indicated there were certain events the CIA did NOT
anticipate. President Diem of So. Vietnam was deposed
& killed. Iranian Revolution: the Shah of Iran was deposed
& a self-appointed cleric claimed the power. The "Arab
Spring."

The CIA had intel, IIRC in July 2001, that terrorists planned
to use planes as weapons. They presented this to Condi Rice,
National Security advisor but she & Pres. George W. Bush
failed to act on it, failed to take precautions.

CW thoroughly explained the WMD, drones w/ missiles
(d w/m ) and waterboarding controversies. George W knew
he had faulty figures when he commanded that Colin Powell
& the CIA Chief Tenant confirm his 'proof' of WMD in Iraq,
George W.'s justification to start the war in Iraq war. I was
surprised to learn d w/m usage started w/ the CIA to destroy
terrorists & Pres. Obama vigorously used this option. Water-
boarding :CIA claimed to have used this on 3 terror suspects
only. I am skeptical about this.

The Director of National Intelligence (DNI) was established
in 2005 to have oversight of 17 US 'spy' agencies, including
the CIA chief. The author indicated the DNI and CIA chief
clashed when their responsibilities overlapped. The role of
the DNI needs to be better defined?

[Miguel · Rating 3 out of 5]

Whipple does a good job with an overview of the CIA largely driven at history of the top level leaders.  It’s tough to grade this as it’s a well researched and written history, but one that doesn’t often get into the obvious thorny morality issues at play.  Whipple discusses the post 2001 torture program and the increased drone strike program under Obama, but it never seems like it should trouble the reader about just what was involved: it’s more like, well, Leon Panetta was just such a mensch who liked to bring in his Labrador to the office and spirits were high at the agency at that time, but much less other than one example of the extrajudicial targeted killings being done in the name of the US.   Therefore as a work of understanding the leaders in the past 70 years at the CIA, bravo?  But in terms of better understanding how the CIA actions have shaped worldwide opinion of the US during the time it doesn’t have much to say. 

[Sarmat Chowdhury · Rating 5 out of 5]

RTC

[Anne Marie · Rating 4 out of 5]

I felt like I was watching a movie! I love biographies and you add spies and CIA into it the mix and you get a awesome book!

I received a copy of this book from Netgalley and Scriber Publishers for my honest review.

[Ryan · Rating 4 out of 5]

Even after finishing Chris Whipple’s The Spymasters: How the CIA's Directors Shape History and the Future, I’m not sure what I’d say the CIA is or how I’d evaluate it and its directors. Here are my initial understandings of the agency.

Evaluation is tricky because at a certain point there is a list of successes and failures, but what I want to do is more or less net them out to “mostly succeeded” or “mostly failed.” George Tenet, for example, served as director during the 1990s and early 2000s. He weaponized the CIA’s drones to empower the agency, he oriented the CIA to respond to non-state terrorism (as opposed to the Soviets or Iraq), and he foiled many terrorist schemes. Tenet warned the Bush administration about September 11th and was ignored. It's tricky to accurately describe the role the CIA played in the invasion of Afghanistan, but it struck me as a key one. He went along with Bush’s invasion of Iraq and even told the administration that they had a “slam dunk” case that Saddam Hussein had weapons of mass destruction. He led the CIA during its era of "black sites" and "enhanced interrogation techniques." He was blamed for the failures of the War on Terror, which to some extent served the president at the cost of the agency. Did he succeed more than he failed? It seems to me he didn’t, but it also seems to me that the CIA as it exists in this century is Tenet’s CIA. Maybe he served the CIA and his presidents well while failing the nation?

I spent a lot of time trying to decide whether (or when) the CIA is effective. Intelligence findings reported here are a bit "hit or miss." The CIA spotted Russia’s plans to place nuclear weapons in Cuba but they were blindsided by the Iranian Revolution. I was mortified reading about the lead up to September 11th. If the directors’ summaries are to be believed, the CIA was catching Al Qaeda chatter about an upcoming “big event.” They saw training grounds rolled up and the terrorists in them dispersed. They knew two of the hijackers were in the USA learning how to fly planes. What did they do? They told Condoleeza Rice and they sent some memos to other agencies, but they did nothing more when those powers ignored them. To me, the CIA engaged in a CYA maneuver, the logic of which goes something like “I sent a note and it’s up to them to follow up so you can’t blame me.” Surely if they took the threats they were announcing seriously they should have done more. This complacency does not seem like an exceptional event. The CIA seems bad at preventing foreign powers from either misleading them or from stealing American secrets. But maybe that’s really tricky and a good success rate is like 40 hits to 60 misses, or maybe some of their successes go unnoticed. When I read how the Trump administration carried out foreign policy, I immediately longed for the stable "good old days" that, up to 2016, I'd read with mixed feelings at best.

What is the CIA? It’s certainly more than an intelligence gathering organization, given its long history of tampering in foreign elections, carrying out crazy missions (like the one seen in the film Argo), and its drone strikes. In trying to characterize the CIA, I eventually concluded that it is a tool for presidents to do illegal things with plausible deniability--its intelligence gathering is subservient to that mission. More generously, the CIA is a sort of release valve that allows for vaguely military responses without calling up the army and fully committing to large scale and long term conflict. Its operating ethos is "fait accompli."

Here's a defense of "fait accompli." The CIA's predator drones, to give just one example, allow the president military options without committing to war, something that should be paradoxical but which may be a more comfortable equilibrium for many countries. The Obama administration was often lauded for staying out of wars, especially after the Bush years, but the CIA under Obama administration is often criticized for its drone strikes. Maybe it’s hard to get the former without the latter, so politicians use the CIA to have it both ways. The efficiency of the illegality, in other words, is desirable until it isn’t, at which point the president can appoint someone to "clean up the CIA." So long as America comes out ahead more often than it loses, maybe Americans and their allies are happy.

Here's one case against the "fait accompli" operating ethos. There is something very tricky in this calculus. At one point, Whipple outlines the murder of a journalist, Jamal Khashoggi, by Saudi operatives. The description is disturbing, so I'll put it under the hood: Khashoggi was escorted to the second floor of the building to the office of the general counsel; suddenly, two men came into the room and dragged him away. He was taken to another room -- where, for the next seven minutes, he was tortured, mutilated, injected with a sedative, and then killed. His fingers were cut off while he was held down. Then he was carried into another room, lifted onto a table -- and dismembered. One of the killers brought a special bone saw for the occasion. He put on headphones and said, "when I do this job, I listen to music. You should do that too." Page 309. America prides itself on being an exceptional nation. Does it want to except itself from culpability if it or its allies do things like this, or does it want to stand apart by not doing things like this? Whipple notes that Trump mostly defended the Saudis after running on bringing back waterboarding and "much worse."

To the extent that the CIA is a tool that allows the president to carry out illegal actions without facing as many political consequences, it is a problem for the CIA as an organization. Because so much of the CIA’s job seems to be dirty work, their influence over and access to the president waxes (the president needs something done) and wanes (the president needs a barrier between the administration and what it has done) relative to other agencies. Each director needs to cultivate a relationship with the president to gain access without sacrificing organizational integrity. Unfortunately, these tensions make the CIA especially prone to abuse. (It’s not surprising to read Whipple’s conclusion about President Trump’s administration and his director, Gina Haspel.) I suspect that the CIA will always struggle with questions like “how much more are we than an assassination squad?” When asked, they seem to dig up dirt on Nixon’s enemies, trade weapons with terrorists, or torture prisoners hidden away in black sites. The organization is largely defenceless against corruption, and only the American voters can protect it. If they want to vote for "waterboarding and worse," they can almost certainly get it.

Spymasters is the first work of non-fiction I’ve read about the CIA, but I finished it with a willingness to read more and to update the initial conclusions recorded here. It is a readable book and Whipple's access to past directors is incredible. I disliked how often he catered to integrating famous “quips” into the history, especially in the more “fast and loose” eras of the CIA’s history. Whipple’s focus is on CIA directors, which means I finished the book without a strong sense of what a CIA operative or analyst does. It seems to me that the agency has almost certainly changed in fundamental ways over the last twenty years—less spy craft and more technical capacity. The nuts and bolts of such changes are not really the focus of this book, but I'd rather read about that time frame than the CIA in the 1960s and 1970s. I finally note that it can be read as an overview of the CIA or as a "what happened" book.

[Denise · Rating 4 out of 5]

Interesting, balanced look at the history of the CIA through its directors, the challenges they faced, the successes and failures on their watch, and the relationship between them and the presidents in office during their tenure. Despite covering a lot of (to me, anyway) familiar ground, this was an intriguing read. Whipple strives for an unbiased account, which he largely manages, though on some issues I found him too uncritically willing to peddle the official line while only few, only mildly critical voices were heard - such as when it came to everybody's favourite CIA euphemism "enhanced interrogation techniques" which he refers to as "unconventional", "harsh", and, when he occasionally feels like sticking his head out a tiny bit more, "brutal" methods while studiously avoiding using the word "torture" except in quotation. Sounds to me like he doesn't take all that much issue with this stuff then, which I very much take issue with.

[Jerome Otte · Rating 3 out of 5]

A clear and well-written work, though it does have its problems.

This book grew out of a documentary on the subject that Whipple worked on. Whipple interviewed Tenet, Panetta, Petraeus and Brennan for the documentary, and the sources are basically the same here (he also interviewed Hayden, though Pompeo and Haspel declined). The narrative also reads like the book version of a documentary.

Whipple looks at CIA directors from Richard Helms to Gina Haspel, and tries to address questions like what kind of people are needed in the role, and what the relationship between a president and a director should be like. If you’ve read up on the publicly known aspects of the Agency’s recent history, you won’t find much new information here. Whipple does a good job outlining CIA’s relationships with the White House and Congress, how they differed from president to president and director to director, and the tensions that result from the president giving illegal orders (Nixon and Helms) or the president disregarding CIA’s intelligence (Trump during the Jamal Khashoggi affair, for example) He also covers such episodes as the Family Jewels affair, and the eventual involvement of CIA directors in life-or-death decisions on what became a global battlefield against al-Qaeda (drone strikes, for example)

The narrative is lively and accessible. As noted before, the format is similar to a documentary; there’s long excerpts from Whipple’s interviews (carefully selected for the best quotes) and the narrative can transition quickly. Whipple occasionally includes excerpts of his interviews in the narrative where he writes in first person, which might annoy some readers. Also, the format doesn’t really allow Whipple to explore some relevant subjects in detail. He often gives concise overviews of a topic that make you wish the book were longer. Whipple also seems most interested in Obama and Trump. When discussing earlier directors, he often brings up episodes that sort of anticipate future events from Trump’s presidency. A lot of the book, unsurprisingly, deals with the CIA’s intelligence failures; known successes are referenced briefly but not really explored.

The book has some questionable statements here and there, or passages that could have been elaborated on. Whipple writes that the coup that overthrew Allende in Chile “had the CIA’s fingerprints all over it.” He doesn’t elaborate. The CIA did fund Chilean political parties and spread anti-Allende propaganda. The Agency’s direct involvement with the coup plotters, however, is less clear; CIA had no known contact with Pinochet, for example, and didn’t know much about him.

When covering the CIA’s rendition, detention and interrogation program after 9/11 he writes “Of course, there were no second wave attacks. That was either because the techniques disrupted plotsー一or because the threat was exaggerated. It is impossible to know which.” Those are the only possible explanations? Isn’t there a possibility that some of these plots were disrupted by standard police work? Or that some of these plots were disrupted by terrorists being captured in CIA renditions or police arrests? Whipple also writes that the Senate Intelligence Committee study on the RDI program “was riddled with inaccuraciesー一suggesting, among other things that neither Congress nor the president had been briefed about the brutal interrogations or the existence of the ‘torture tapes.’ The truth was, Feinstein, House majority leader Nancy Pelosiー一and George W. Bushー一 were all informed.” These points are also controversial. Apparently, Pelosi wasn’t fully briefed until later; CIA actually declassified documents on these in 2010, and, according to them, Pelosi didn’t attend the briefings in 2002. These documents also state that Congress was only told of the John Yoo memos in February 2003, so how could Pelosi have learned of the techniques at a meeting in September 2002 (the date given on a CIA list released in 2009)? The oversight committees weren’t briefed until 2006; the briefings before that were restricted to the “Gang of Four.” As for Bush, it is not clear to what extent he was briefed on the program’s details (partly due to incomplete CIA records) In his memoirs Bush says Tenet briefed him, but according to John Rizzo, Tenet had no recollection of such a briefing. According to the Senate report on the program, Bush wasn’t briefed on the techniques until 2006.

The book also includes some errors. When covering Lebanon in the 1980s, Whipple writes that “Reagan didn’t retaliate militarily for the Beirut bombings”; he doesn’t mention the air strikes Reagan ordered in Lebanon afterwards. Whipple also claims that al-Qaeda’s origins can be traced back to the Afghan mujahideen, a common assertion, but one that makes no distinction between the Afghan and Arab fighters. Carlos the Jackal is called an “Algerian” terrorist. Whipple writes that Stanley McChrystal was forced to resign after disparaging Obama officials. McChrystal’s staff did make disparaging statements, but did McChrystal? Whipple also writes that Trump revoked John Brennan’s security clearance, although Brennan has denied it. he also writes that Yuri Nosenko was put into solitary confinement on James Angleton's orders, even though the Soviet division directed that this be done. He refers to Iran-Contra as a “failed covert action.” He also writes that Aldrich Ames was arrested on his way to meet his “Soviet handler” (Russian would be a better word, and Ames was actually heading to his office) He also repeats the common story of Dennis Blair and Panetta arguing over station chiefs, even though that dispute was about intelligence liaisons.

There’s more examples of these. Whipple’s coverage of the various CIA and FBI intelligence failures related to 9/11 seems fair and accurate enough. At one point, however, he mentions that Khalid al-Mihdhar and Nawaf al-Hazmi were never put on a no-fly list. Whipple doesn’t mention how different these lists were before 9/11 from what we have today. The State Department did manage a watchlist at the time, but it did not have a “no-fly” provision that airlines could access as passengers checked in. Whipple also describes the CIA’s post-9/11 rendition, detention and interrogation program and mentions the death of detainees in CIA custody, such as Gul Rahman in Afghanistan. He also mentions a detainee death in 2002 at an “Iraqi prison.” Apparently, Whipple means Manadel al-Jamadi, who actually died at Abu Ghraib in 2003.

A few parts of the book are strange. “Brennan had the slightly jaded air of the sergeant on the TV show Hill Street Blues, who admonished his cops on the morning roll call, ‘Let’s be careful out there.’” I’ve never heard of Hill Street Blues, but hopefully every other reader has. Another part is way weirder. Admittedly Whipple is quoting a source here, but I have no idea why it's included. Whipple quotes a former DNI on Republicans and their foot-dragging on Russian operations during the 2016 elections, linking it to their opposition to Obama: “I think it was because he’s black. No one overtly said that. But I think there was a lot of resentment among Republicans about that.” Obviously, that doesn't make much sense. What also doesn't make sense is why Whipple even includes this. He doesn't even make any comments about it.

A sharp and insightful work, if a bit breezy.

[Kulturowa.Anihilacja · Rating 5 out of 5]

CIA agencja zdecydowanie mniej medialna aniżeli wszechobecne FBI, a jednak kluczowa i niemal fundamentalna, bowiem największa agencja wywiadowcza świata ma wpływ na znacznie więcej rzeczy, niż może nam się wydawać.

Współczesne szpiegostwo coraz częściej przyjmuje formę cyfrową, bowiem przechwycone odpowiednio wcześnie informacje mogą być groźniejsze niż rakiety. Autor wraca jednak do korzeni działalności wywiadu, do klasyki działalności pod przykrywką, nieformalnej ukrytej głęboko w cieniu. Ta książka to zdecydowanie więcej niż historia CIA, to portret ludzi będących na czele najpotężniejszego wywiadu, a oprócz tego poznajemy, jak wpływali na losy milionów ludzi, licznych państw, rewolucji, wojen, a nawet doprowadzali do pokoju.

Bije z tego reportażu rzetelność poparta licznymi dokumentami, które ukazuje dyrektorów CIA jako bohaterów niejednoznacznych i często pełnych sprzeczności od idealistów przez technokratów, a także strategów stosujących różne narzędzia do politycznych gier. W reportażu nie znajdziemy tylko laurek i pieśni pochwalnych, bo Whipple pokazuje, jak ci ostrzegający przed katastrofami nie zawsze zostali wysłuchani, jak inni popełniali błędy, przykre w konsekwencjach, z którymi świat boryka się do dziś.
Ważnie dla mnie okazało się to, że autor opiera się w swojej publikacji na licznych rozmowach z dyrektorami i ich współpracownikami co podkreśla autentyczność książki i nieco ją dynamizuje. Było we mnie takie poczucie podczas czytania, że zaglądam w nieco zakazane rewiry, gdzie jestem świadkiem briefingów, odczuwałam ciężar decyzji, które często wymagały błyskawicznej odpowiedzi. Autor nie boi się tematów trudnych, których wiele osób chciałoby uniknąć jak nieudane misje, skuteczność w czasach dezinformacji i cyberwojen, inwigilację obywateli, czy tortury.

Whipple ma talent do analizowania mechanizmów władzy, ponieważ ukazywanie relacji między agencją a poszczególnymi prezydentami były niezwykle wciągające i interesujące. Brutalnie ukazane jest także to, że CIA często w konfrontacji z polityką jest bezsilna, bowiem polityka rządzi się swoimi prawami.

Dla mnie „Arcyszpiedzy” to pasjonująca, wielowarstwowa książka służbach i ich ludziach, którzy często są w oku cyklonu globalnych kryzysów. Pomimo polityki ta książka jest bardzo ludzka i powiada o bezsilności, pokusach, odpowiedzialności. W obecnej sytuacji geopolitycznej ta książka jest zdecydowanie konieczna do przeczytania.

[AliceC09 · Rating 5 out of 5]

This book is fascinating and exceptionally well written. The book covers the presidencies of Kennedy through to Trump (ending in early to mid-2020, with discussions of Covid-19). What makes that book as insightful and impressive as it is is the calibre of interviewees that Whipple was able to cultivate. They include every living director (only those who served Trump declined) as well as a host of employees who held a variety of opinions.

As someone who has done interview based research myself with government officials I have even more appreciation for the work that Whipple has done.

I definitely want to go and read his previous book on White House Chiefs of Staff.

[Phil · Rating 3 out of 5]

I very seldom read books about this sort of thing. Especially one written so recently, 2020. Although the book was intriguing it was also predictably one sided. Much praise for Democratic administrations while putting down the Republican ones. I don’t need to read books that match my political views but it would be nice to read a clearly non -bias one, this wasn’t that. If the Director of the CIA is meant to focus on intelligence and not policy, free from partisanship, why couldn’t Whipple’s book be the same? We’ve had bad presidents and good ones on both sides of the political lines. I can’t imagine being the head of the CIA is easy no matter who sits in office.

[Girard Bowe · Rating 5 out of 5]

An exceptional overview of the intelligence agency heads, from the JFK administration through DJT's. Not a deep dive into all of the CIA's exploits, The Spymasters concentrates on the various personalities and politics. The hardcore intelligence reader may find nothing new here, but as a casual reader of history and current events, I thoroughly enjoyed this book. Even if one is familiar with most of the stories, there are interesting details that make this well worth reading. The Spymasters is very readable, as was his previous book, The Gatekeepers.

[WM D. · Rating 4 out of 5]

The Spymasters was a very good book. This book is the second book I have read by him and I truly enjoyed his writing. Amazing facts I didn’t know before.

[Joseph · Rating 4 out of 5]

I learned a lot reading Chris Whipple’s THE SPYMASTERS: HOW THE CIA DIRECTORS SHAPE HISTORY AND THE FUTURE, and I’ve already forgotten most of it.

The introduction was an eye-opener. If you don’t read the book, visit your local library and read the introduction.

A couple things I came away with: the CIA (Central INTELLIGENCE Agency) is one of fifteen intelligence agencies in the U.S. Government. That’s a lot to me. Apparently to Congress, also, who after 9/11 set up the Director of National Intelligence (DNI) to coordinate all the spy agencies. The CIA is the principal intelligence agency. The DNI is the head of intelligence gathering, though, and technically the CIA Director answers to the Director of National Intelligence (good luck on that). The DNI is responsible for being the president’s chief intelligence officer and overseeing the President’s Daily Brief (PDF). But the CIA prepares the PDF and briefs the President on it.

The CIA is the chief intelligence agency, but it’s function is human intelligence (you know – spies and double agents and moles and assets and counter intelligence - that sort of stuff). But we also get intelligence information from electronic signals and systems such as communications systems, radars, bugs and weapons systems (known as SIGINT – short for Signal Intelligence). I would have thought that was under CIA control, but no, that’s the National Security Agency (and the NSA has more personnel than the CIA). The NSA shares its information with the CIA, but I bet there’s a lot of inefficiencies.

The CIA in practice has two arms. On one hand there are the Analysts, who spend their lives analyzing and decoding all kinds of information about foreign governments and terrorist groups. These are described an intelligent “introverts without tans.” The other group are the operatives, the clandestine faction who make for good movies and novels – brash, charming, secretive. In theory both groups are intelligence gatherers. Somehow and sometimes the CIA engages in Covert Operations, like killing people and overthrowing governments. How much covert activities the CIA engages in ebbs and flows depending on who the CIA Director and Presidents are at any given time.

In theory (and apparently in practice) The CIA gathers information and presents it to the President. The CIA does not argue for any policy. The CIA merely gets the information for the President and his cabinet, and it’s the President and his people who formulate policy. In fact, after President gets data, the CIA briefer usually leaves the room. Presidents differ on how they use the information (if at all -It seems too many Presidents only want to hear information that backs their world view.)

The CIA Director informs the President, but is accountable to Congress (who some time are at odds). The Director to be successful must support his or her CIA operatives and analysts. The Director who can’t or refuses to do all three doesn’t last long. If the CIA royally screws up, the Director often takes the fall and is replaced.

There is no “one type” of CIA Director. They can be dignified or brutish, quiet or garrulous, a lifetime CIA operative or an outsider, military background or civilian. Some directors are more successful than others.

The book is about those directors and the tough situations they faced during their tenures. Some come out looking good in the book. Others don’t fare so well.

Overall I learned a lot and recalled events that were blurry when they occurred (anyone remember Iran-Contra fiasco) (or 9/11 – CIA many times notified Condoleezza Rice about impending terrorist attack between July and September by the way) (or Beirut) (or killing bin Laden) (or a host of other front page news events).

Maybe because there are so many people discussed and so many events and so many agency initials invoked, it was hard to piece it all together, which keeps this book from being five stars.

My rating: 4 stars

[John · Rating 4 out of 5]

A readable account regarding the relationship between CIA directors and the head of the Executive Branch. The book begins with LBJ and ends with Trump. Whipple's book is safe. What I mean is he addresses the morality of the CIA's actions in a non-judgmental way. He brings it up but does not really address it in detail. The strength of the book is the relationship of the CIA directors and the presidents. Some of the directors were clear cut choices while others I was extremely puzzled why the president chose this individual to lead a major spy organization.

The book was interesting to read and can be read quickly. I recommend this book with Tim Wiener's book about the CIA called The Legacy of Ashes. One difference is Whipple's books presents some successes the CIA had whereas Wiener mostly gets into the failures of the organization, but he admitted that the CIA is not really going to broadcast the success stories because those methods can be used again. An interesting read with flaws.

[Stanley Xue · Rating 3 out of 5]

Interesting book about the CIA directors and the political events and intelligence operations that occurred under their directorship.
Published in 2020 - so even include an epilogue discussing the pandemic response.

[Ted Haussman · Rating 5 out of 5]

A superb book that examines all of the CIA directors from Richard Helms to the present. Whipple interviewed most of these former CIA directors and the insights are invaluable.

Fascinating book.

[Rebuma Dejene · Rating 4 out of 5]

A fascinating historical and contemporary account of the CIA and how the US's Intelligence apparatus plays a significant role in shaping the Presidency and US foreign policy. A good book on the practical world of the art of US Spycraft from the post WWII to the Trump Presidency. The book provides a detailed study of the role and impacts of different variants of leadership in the intelligence apparatus and its consequential ramifications for the US national security and global order. Chris Whipple explains the often intriguing and interesting relationships between elected presidents of the US and appointed political leaders in navigating through the complex world of bureaucratic apparatus, international affairs and personal relationships that matter. The book provides important insights about the secretive world of the intelligence machinery and people who have been running it through different chaotic historical episodes of the US and world. From a global perspective, the WWII, the Cold War, the so-called global war on terror, and the post Cold War periods are taken into account from a US intelligence perspective. And interestingly enough, how the intelligence apparatus is often used as a personal political instrument for Presidents and for achieving narrowly driven shallow foreign policy goals leading to dangerous consequences for the world and the US. A definitely important book with fascinating insights and history of the Failures and successes of the US since the WWII.

[Kwame Som-Pimpong · Rating 5 out of 5]

Fascinating read.

[Luca Trenta · Rating 4 out of 5]

You views on this book will largely depend on who you are as a reader.

if you are an expert on the topic and if you have done some research on the CIA, you will be able to admire and envy Whipple's access to current and former CIA Directors and officials. The amount of interview conducted is absolutely impressive and the book is peppered with very interesting quotes taken from these interviews. However, if you are an expert, you will also find very little that is new in the book. There is some more confirmation that the CIA had a role in the killing of Mugniyeh, and a few other small revelations, but not much else.

If you are not an expert, this is a good book to start exploring the (recent) history of the CIA and, more specifically, the complex relationship between the President and his spymasters. The chapters are fairly short and the narrative is engaging. They provide an overview of key (and famous) episodes in the history of the CIA. The narrative details moments of friction between the CIA and other political actors (e.g. Congress), but mostly focuses on the CIA Directors and their roles in various presidencies.

The book overall makes a fairly convincing argument that the Director should be a honest broker and a provider of intelligence. It makes the case that, since 9/11, the CIA has moved too much into the killing business at the expense of its intelligence analysis and collection role. The book concludes with a well-substantiated indictment of intelligence under Trump. Both Pompeo and Haspel acted more as partisan hacks than as CIA Directors.

[Patrick · Rating 4 out of 5]

This book is structured similarly to Whipple's earlier masterpiece on White House chiefs of staff. It includes profiles of CIA directors going back decades, with a heavy focus on their interactions and relationships with the White Houses they served, as well as some focus on why some D/CIAs have been more effective and/or successful than others. To me, The Spy Masters falls short of Whipple's earlier work on WH chiefs of staff, but this is still a great read for students of intelligence history.

[Randal White · Rating 5 out of 5]

An easily read and digestible book on the men and women who have led the CIA. The personalities, the successes and the failures, the results (intended and unexpected). The book flows along well, from director to director. Along with a lot of personal insights by the former directors.
Where the book really shines, in my opinion, is in what it tells of the events of the past several years. Truly horrifying. Let's hope the cooler heads prevail.

[Michael · Rating 2 out of 5]

Some interesting anecdotes. A few insights into how staffing decisions and interpersonal relationships shape the fate of large government bureaucracies. But the author seems overly credulous of those he interviewed, and the end result is rather thin history.

[Bill Manzi · Rating 4 out of 5]

Chris Whipple has come up with a fine book giving us a look at CIA Directors, starting in the Kennedy/Johnson era. I read Whipple’s “The Gatekeepers” which was a very insightful book about White House Chief of Staffs. He has used the same techniques here, gathering the thoughts of CIA Directors still alive through interviews which offered some excellent commentary.
Whipple gives us a look at the Directors, and how they interacted with the Presidents they served, starting with the most fascinating of spies, Richard Helms. Helms was a career man at the agency, and was in a position of authority, but not director, during the Bay of Pigs fiasco that caused so much turmoil at the Agency. Whipple shows us Helms, the expert bureaucratic infighter, not being “in the loop” on the Bay of Pigs planning. He was in a position of authority when the CIA, under orders, embarked upon Operation Mongoose, a plot to assassinate Fidel Castro with the help of U.S. organized crime figures. The Helms material is augmented by interviews with his widow Cynthia, and Whipple’s treatment of Helms, in certain instances, may be considered overly generous. Whipple reports Helms statement that when he took over as DDP in 1962 he “shut down” the CIA assassination plot against Castro. Whipple acknowledges that the evidence does not support Helms on that score. Helms took over as Director after appointment by LBJ, and as Director was charged with providing intelligence on North Vietnam. In this, the first Director covered, we see the constant theme of the Whipple effort. Helms provided intelligence on the Vietnam War that was not to LBJ’s liking, with LBJ simply ignoring the analysis that he disagreed with. (The CIA provided a 250 page analysis “The Vietnamese Communists Will to Persist” that was pessimistic about the U.S. ability to achieve its war aims) Helms in this instance did his job but determined that pushing LBJ on that score was not prudent for the agency.

“Helms reached a point where, in the morning briefings and the President’s daily brief, we just slacked off on providing information on Vietnam, said analyst Kerr. We did not do the aggressive pieces that were negative because they were counterproductive.”

The Spymasters Whipple Chris p 37.

Despite the recognition that LBJ was not receptive to this line of analysis Helms CIA took on the so called “domino theory” which argued that a U.S. withdrawal from Vietnam would lead to a communist wave of takeovers in Southeast Asia by producing “Implications of an Unfavorable Outcome in Vietnam” which diplomatically called into question the domino theory. Helms may have not pushed LBJ too hard but he kept producing analysis that was honest, and not what the President wanted. He walked a tightrope, including having to deal with demands by LBJ for domestic surveillance of the anti-war movement, a violation of the CIA Charter.

The Helms portion of the book, as mentioned, in some fashion sets the stage for the rest of the Whipple effort. How does the CIA Director maintain relevancy, and access to the President, if the intelligence being provided does not dovetail with what the Presidents desires? We get to examine the George Tenet “slam dunk” to George W. Bush on Iraqi WMD. A great section on the time of George H.W. Bush as CIA Director, considered by most observers to be a successful tenure. (Bush felt, with some justification, that he had been maneuvered into the slot by rival Donald Rumsfeld, who was looking to isolate Bush into what he believed to be a dead end job politically) Ronald Reagan’s Director, William Casey, led him into what became the Iran-Contra scandal, which wounded the Reagan presidency.

The book, from my perspective, gets high marks, giving us an overview of the Agency, and how it operates. Enhanced interrogation techniques? Yes we get a pretty good back and forth on that, and so many of the issues that have dogged the agency over the years. One theme referenced by Whipple is the Washington cliche that "there are only policy successes-and intelligence failures.” With the recognition, articulated by former Director Bob Gates, that “the CIA has one protector, and one customer, and if you can’t get that relationship right then the agency is screwed” the Agency has unfortunately molded intelligence to that reality. Whipple has given us the good, the bad, and the ugly in this book. We even get a quick look at James Jesus Angelton, likely the most impactful non-director to ever work at the Agency. More on Angelton in the fine book “Wilderness of Mirrors.” Pick this one up!

[Dominic · Rating 5 out of 5]

Bookstores are filled with biographies of presidents, especially Washington, Lincoln, and the Roosevelts. There are even numerous biographies of prominent senators and representatives. I've appreciated Chris Whipple's books for highlighting unelected public servants who are often just as important as the people we see in the news every day. Whipple's "Gatekeepers" was a fascinating look at the chiefs of staff who helped the White House run smoothly - or failed to do so. In "Spymasters," Whipple turns his attention to the CIA directors. Like "Gatekeepers," the book expands upon a Showtime documentary (also by Whipple).

CIA directors typically have an internal and external role. They manage one of the most important and powerful intelligence services in the world. The director needs to both defend the agency staff to preserve morale and be able to push for reforms against bureaucratic fiefdoms when appropriate. They also need to ensure that the president receives the agency's intelligence products. The director needs to have a good relationship with the president, but also tell him (or her) politically inconvenient truths.

Whipple focuses on both aspects of the job, but generally the book focuses more on the politics and relationships with the president than the day-to-day management of intelligence services. Each chapter focuses on a particular director - or directors if their terms were short - and his or her relationship with the president.

Indeed, it becomes quite clear that the CIA has had its share of political drama during the past 70 years. Agency directors have found themselves in the middle of high-profile political controversies, and not only related to the gathering of intelligence abroad. Overall, Whipple's assessment of the CIA is fair and generally favorable to the directors, although he does paint a picture of a surprisingly beleaguered agency. At several points, the agency faced existential crises that almost led to its shuttering.

Then again, as several directors noted, in Washington, there are policy successes and intelligence failures. Politicians have regularly tried to deflect blame for their mistakes onto the intelligence services. Few directors emerge from the job without at least some intelligence failures on their watch.

Unlike "Gatekeepers," which concluded with a fairly clear set of "best practices" for White House chiefs of staff, "Spymasters" ends on a more ambiguous note. There isn't a single model for success at the agency. Whipple gives high marks to Robert Gates - who rose up through the ranks as an analyst - and Leon Panetta - a consummate politician and outsider. To some extent, the only recipe for success is intelligence, hard work, and luck.

[Note: I received a copy of this book from the publisher in exchange for an honest review.]

[Nancy · Rating 5 out of 5]

I found this book exceptional. I am a few years older than the CIA itself and have therefore lived through its entire history, observing the media news surrounding its activity and its directors. That made the material here especially relevant to me and revealed the agency itself lying beneath the tip of the iceberg we are able to see on the daily news. As the events of history unfolded after the inception of the CIA in 1947, I was busy with my life--growing up, going to school, raising a family, working at my profession. I saw it all vaguely, distracted by so much else--by life itself. But Chris Whipple, in this well organized and executed account, crystalized the major events of the last 70 years by using, as his template, the careers of each CIA director and the impact they had on our world.

I began to have a far better understanding of those somewhat fuzzy images and commentary that had whisked past on our television every day for 70 years. I was introduced to each of the directors through their biographical sketches and began to better understand the choices and decisions they had made, options that had often directly impacted our lives. While I fixed dinner or washed the laundry, they influenced the fate of nations and leaders, swayed our presidents, and impacted history. They were all significant people, talented and flawed, wise and foolish, a mixture of these and other character traits. Whipple presented each of them fairly in the context of their time, along with the presidents they served.

I listed on paper each director with the president(s) he or she reported to in order to keep them clear. While listening to this book, the history I had lived through began to click more firmly into place. The author opened his book with an introduction of the topic, listed his objectives, and gave several concrete examples. Then he proceeded to march through the succession of CIA directors, sequentially, until coming finally to the first woman, Gina Haspel, who currently serves at the pleasure of Donald Trump. In the Epioogue, he reviews the questions previously raised as to the CIA's responsibilities, its conflicting requirements for secrecy and oversight, and the difficulties of reporting unwelcome intelligence to presidents who each have their own political agendas. Whipple has informed opinions which he states, but he also shows great respect for the men and women who serve this vital, complex, controversial government agency at all levels.

For me, who lived through it all, this was clarifying. I learned about the CIA, its brilliant successes and its shameful failures...but in the context of the political and global stresses of their times. I credit the author and commend him for the structure and content of this book. I learned so very much and enjoyed the process thoroughly.

[LuAnne Feik · Rating 5 out of 5]

In the process of describing the directors responsible for leading the Central Intelligence Agency since its inception after World War II, THE SPYMASTERS lays bare four systemic problems that affect the intelligence supporting U.S. national security.
1) Conflicting attitudes within CIA toward analysts, covert operators, technology, a mole/spy (Rick Ames and enabler, James Jesus Angleton) and women have, and do, affect morale, hiring, firing and intelligence collection and reports.
2) On paper, the responsibilities of U.S. agencies and departments, embassies and foreign intelligence services seem clear. In practice, the coordination and cooperation involved in collecting, evaluating and acting on intelligence is extremely complicated.
3) Political and other considerations prevent presidents and the intelligence community from always sharing the same objectives.
4) There is a built-in tension between Members of Congress, primarily attorneys schooled in the rule of law, and the intelligence community's determination to stretch legal limits to complete a mission.
(For a more detailed discussion of these four problems, go to the post, "4 Problems of U.S. Intelligence", at globalizationforkids.blogspot.com)
No one book provides a complete review of the tools, procedures, limitations and capabilities the U.S. intelligence community uses to protect national security. As Chris Whipple surely knows, the CIA directors and others he interviewed for THE SPYMASTERS were motivated to protect their legacies and the integrity of the Central Intelligence Agency. Their perceptions also reflect their personalities and their loyalty to and chemistry with associates.
Predictably, CIA's current director, Gina Haspel, and Michael Pompeo, the current Secretary of State and Ms. Haspel's predecessor, declined to be interviewed, since anything they would say could have repercussions related to their ongoing responsibilities. It was unfortunate to see how the good ol' white, male and Yale CIA boys used Ms. Haspel's lack of response to a request for an interview as an opportunity to take their long knives to her experience, decisions and behavior.
In the final analysis, however, THE SPYMASTERS reminds citizens of democracies how free they are to discover the way their governments work and how free they are to correct what they dislike.

[Matthew Spencer · Rating 4 out of 5]

I read very little non-fiction, and almost all the non-fiction I do read is about terrorists, spies or pop management trends. So a book about the management of spies is right up my alley!

The most impressive part about this book is the author's phenomenal access: he interviewed every living CIA director and a wealth of other famous politicians in the writing of the book. It is spectacularly researched and contains some fascinating inside baseball as a result. The second thing that impressed me was the sweep of history that the book traced out, covering Nixon to Trump in a breezy 330 pages. The long coverage lets the reader see the national security apparatus unfolding from its origins and trace recurring characters, which I felt added a great deal to the experience.

The long sweep means the book is necessarily a survey, so each CIA director is boiled down to a few key talking points: John Deutch made drones, George Tenet routed the Taliban and whiffed WMDs, etc. It works because of Whipple's evident skill at stitching together narratives. He plays wiht chronology and interviews editing in fascinating ways to tease a story out of headlines that would otherwise be confusing.

The book didn't improve my opinion of the CIA, which seems to have been in crisis since its inception. It's a very strange organization, with frightening and often extrajudicial power. It also has a long track record of high profile misses (though the book emphasizes that (A) successes may be secret and (B) history is written by politicians eager to use spies as scapegoats), which have driven American national security adventures and misadventures for decades. I like that the book gave me material enough to judge the agency intelligently with a journalistic flair for neutrality.

I had a lot of fun with this, to the extent that it became a page-turner that kept me up past my bedtime in multiple chapters. I also liked how it interlocked with other books on the subject that I've read recently: though the pace was brisk, no stone was unturned, even a unflattering shout-out to Ali Soufan (who wrote Anatomy of Terror, which I reviewed last year). If your non-fiction interests are anywhere near mine, or you'd like some context for American history or some grist for the next time you argue with a spy, I recommend this highly.

[Dave Reads · Rating 4 out of 5]

"Spymasters: How the CIA Directors Shape History and the Future" take each CIA Director and describes how they were appointed, their relationships with the President and Congress, as well as how each excelled and failed. Chris Whipple presents a very detailed and well-reported chapter on each Director.

Whipple goes through each CIA director chronologically. We see the differences between each Director, their personalities, and ambitions. Some were highly principled, while others were much more political.

We see how the CIA adapts to each leader. It's a complex organization with important responsibilities. When most of us think about the CIA, we think of the spies gathering information or operatives who can infiltrate another nation's power structure. What we don't usually think about is the politics that surround the agency. Sometimes presidents ask for things that are illegal or impossible. And each chief executive treats and uses the information in different ways.

While Presidents pick individuals to head the CIA, this book sheds light on how those relationships deteriorate over time.

And each Director approaches the job differently.

Richard Helms wasn't afraid to warn Lyndon Johnson and Richard Nixon that efforts to win the war in North Vietnam were not going well. He agreed to spy in anti-war protestors.

Allen Dullea used the agency to overthrow governments in Iran and Guatemala but then botched the invasion of Cuba.

William Casey's tenure included the Iran Contra affair, which "almost sank Ronald Reagan's presidency."

Some directors had close relationships with the president's they served: Leon Panetta, William Webster, Robert Gates, John Brennan

While the 9/11 attacks were a surprise to the CIA, warning signs were ignored.

Anyone who follows the news won't necessarily find new headlines, but we get more details on many of the stories because of the author's interviews and research.