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"One Hell of a Gamble": Khrushchev, Castro, and Kennedy, 1958-1964

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Based on classified Soviet archives, including the files of Nikita Khrushchev and the KGB, "One Hell of a Gamble" offers a riveting play-by-play history of the Cuban missile crisis from American and Soviet perspectives simultaneously. No other book offers this inside look at the strategies of the Soviet leadership. John F. Kennedy did not live to write his memoirs; Fidel Castro will not reveal what he knows; and the records of the Soviet Union have long been sealed from public view: Of the most frightening episode of the Cold War--the Cuban Missile Crisis--we have had an incomplete picture. When did Castro embrace the Soviet Union? What proposals were put before the Kremlin through Kennedy's back-channel diplomacy? How close did we come to nuclear war? These questions have now been answered for the first time. This important and controversial book draws the missing half of the story from secret Soviet archives revealed exclusively by the authors, including the files of Nikita Khrushchev and his leadership circle. Contained in these remarkable documents are the details of over forty secret meetings between Robert Kennedy and his Soviet contact, records of Castro's first solicitation of Soviet favor, and the plans, suspicions, and strategies of Khrushchev. This unique research opportunity has allowed the authors to tell the complete, fascinating, and terrifying story of the most dangerous days of the last half-century.

420 pages, Paperback

First published August 1, 1981

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Aleksandr Fursenko

7 books6 followers

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Displaying 1 - 26 of 26 reviews
Profile Image for Jan-Maat.
1,687 reviews2,500 followers
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March 14, 2019
It is possible to imagine the cold war as a kind of ultra chess game played by teams of mostly elderly white men who while keen to out wit their opponents abided by certain implicitly understood rules.

Fursenko and Naftali's 1997 book suggests a very different vision, one in which those with the theoretical power, authority and the very real nuclear weapons, were struggling to gain control and to create some kind of order.

From this point of view the nominal leaderships can be seen as victims, firstly on the US side where misinformation lead to increasingly aggressitive policies towards Castro that transformed him into the full blown supporter of the Soviet Union that the US feared that he was from the start, and after the Bay of Pigs, rebuilding a friendly US-Cuba relationship would not be an easy task, while on the Soviet side transfixed by dimming memories of the revolutionary recreation of their own country, the dog found itself being wagged by its tail until both sides found an accommodation that allowed them to trample on the little guys.

The book was the fruit of co-operation of an American and a Russian historian and the product of research in the archives of both countries. As a result the narrative provides insight in the thinking and fears of both sides as the crisis develops out of the strategic possibilities arising from Castro's success in Cuba. It is a fairly lively tale starting with the Castros coming to power, the Kennedy election and the bay of pigs, ending with the fall of Khrushchev, the focus is on the Russians and the Americans, what the Cubans thought or pushed for is seen through the prism of Soviet or American opinion.
1 review
July 25, 2010
This is it. If you wished to dive into the Cuban Missile Crisis then you have found your starting point. Both American and Russian archives lend this work an unprecedented amount of detail. One small caveat: I wish the Cuban side of the crisis was fleshed out further following the decision to send nuclear weapons to the island. But Fursenko and Naftali did not have such clearance with the Cubans so they can hardly be blamed. Despite such detail, One Hell of a Gamble does not plod along. It is a fantastic book that history nerds and regular readers will enjoy alike.
Profile Image for Meg G.
22 reviews3 followers
October 11, 2010
This book was an interesting approach to the Cuban Missile Crisis. While it did an excellent job of portraying events in Moscow and Washington, D.C. I found the portrayal of Fidel Castro as overly simplistic. The approach taken casts Fidel as a prisoner of his own thought, indecisive, and an incapable leader as he forged a path to communism in Cuba in the early 1960s.
Profile Image for Courtney.
319 reviews7 followers
May 12, 2018
This book is incredibly dense, but so well researched and thoughtfully organized. Context is brought to so many of the decisions made at the time and so many primary resources were used. This is THE book to read if you're interested in understanding the Cuban Missile Crisis.
5 reviews1 follower
November 22, 2012
Gained a lot more respect for Castro and insight on a behind the scene read on the Cuban Missile Crisis
Profile Image for Nolan.
3,747 reviews38 followers
August 22, 2021
You just never know how a kid is going to turn out. This book opens with a super-brief look at Castro’s childhood and the fierce denunciation by nun who taught him that he would ever be a communist. The authors fill the book with bits of information about which I had no knowledge, and that’s what made it a fascinating read for me. I had no idea, for example, that Castro’s rebels kidnapped American and Canadian armed servicemen and civilians in the summer of 1958. (Hey, I was only six months old; I get a pass for not knowing about this.) The rebels demanded that Washington stop selling arms to Cuban Dictator Batista and pledge not to use the naval base at Guantanamo to stage a military crackdown on Castro and associates. Eisenhower prudently suspended the aircraft deliveries, and the communists prudently released the hostages. But the relationship between Washington and Castro would be sour at best from then forward.

When he blitzed America with his six-city summer tour in 1959, Cubans had the second highest living standard of any Latin-American nation primarily due to U.S. investments in the region, according to the authors. While attempting to charm the American people, he denied vociferously that he leaned toward communism. While visiting Harvard as part of that tour, Castor pointed out that the school rejected his application. School officials eagerly promised him a slot in the upcoming school year if he wanted it. What a different world had he taken them up on it.

The book credits Raul Castro as the point man who brought together Cuban and Kremlin officials, all this while Fidel repeatedly denied that communism would be part of his new government. The initial rivalry between the Castro brothers is fascinating. Raul got support from Che Guevara. Fidel gradually changed when he saw Soviet support coming in the form of weapons.

You’ll walk with these authors the tortuous path to the Bay of Pigs debacle, and while modern images from Afghanistan smack of another debacle, you’ll at least be able to recall from this book that it isn’t the first time. Smarting from his failures at Bay of Pigs, Kennedy seems obsessed with Cuba, according to the authors. He even plans another invasion, this time with plenty of air power, possibly after the congressional elections.

That invasion never happens, because Khrushchev decides if Kennedy can plant missiles in Turkey, Khrushhev can plant missiles in Cuba. Stalin had no desire to spread communism to the Caribbean, believing he had enough to do in eastern Europe. But that didn’t stop Khrushchev.

You follow detailed cabinet-level conversations wherein Kennedy and friends debate the merits of a full-on air strike designed to disable the missiles before they can be operational to a blockade that would prevent the Russians from bringing additional nuclear firepower into the region. We know how the story ends—Kennedy pulls already aging Jupiter missiles out of Turkey, and Khrushchev reluctantly brings home his arsenal.

The authors then explore the aftermath of the missile crisis. In tiresome fashion, they speculate on whether the Cuban Missile Crisis indirectly caused Kennedy’s death or whether Oswald indeed acted alone as the Warren Commission claimed. They link Khrushchev’s humiliating demise in 1964 in part to the Cuban standoff.

I wish I had read this when it was first available. I might have had less difficulty processing a long parade of names, mostly foreign. I find these days if you force me to deal with seemingly endless lists of names, I struggle trying to keep everyone together and remember what their role is. That’s a reader failure of mine.
Profile Image for Bryan Whitehead.
584 reviews7 followers
April 26, 2020
Fursenko and Naftali use newly-available Soviet archives to flesh out the story of the Cuban Missile Crisis. As a result, this is a wonderfully multi-faceted account of the most dangerous episode of the Cold War. The authors begin with Castro’s rise to power and describe his transformation from independent revolutionary to Communist dictator. The book also extensively recounts the thinking on both sides of the Iron Curtain as the crisis unfolds. What emerges is a portrait of two superpowers gearing up for a massive war using a relatively unimportant Caribbean island as a pretext. Both sides desperately grasp at the chicken switch at the last second, for which future generations may be eternally grateful. One hell of a gamble, indeed. This is a must-read for anyone with an interest in the subject.
Profile Image for Borislav Boev.
40 reviews6 followers
February 11, 2023
Изключително информативна книга за кубинската ракетна криза! За да разберем най-добре една криза от такъв исторически мащаб, трябва детайлно да проучим позициите, интересите, мотивите и политическите процеси в съответните страни. Всеки, който се интересува от дипломацията при международните кризи трябва да я прочете. Особено в контекста на днешните международни събития.

A very informative book about the Cuban Missile Crisis! In order to understand a crisis of such a historical scale, we need to study in detail the positions, interests, motives and political processes in the respective countries. Anyone interested in diplomacy in international crises should read it. Especially in the context of today's international events.
Profile Image for Evan Bolick.
139 reviews
October 3, 2023
An interesting book that chronicles the rise of Castro and the brinksmanship that ensued with the first Communist regime in the Western Hemisphere. However, the book is incredibly dry and more like a lecture than a compelling narrative.

Unlike a lot of analyses on the Bay of Pigs "invasion" (so poorly executed and undermanned, it's more of an incursion) and the following nuclear missile crisis, this book doesn't really present Khruschev, Kennedy, or Castro (and their respective advisors) as having avoided global annihilation due to any sort of prescient forethought or masterful strategy. Rather, it seems as though indecision and a realization on both sides that nuclear war was far too ruinous saved the day (except Castro who claimed he was ready to go all the way, but is presented as a player with little to no say in these events other than acting as a catalyst for a larger struggle between the US and USSR).

This book is impressively and exhaustively researched (according to my Kindle, roughly 25% of the total page count are citations). I'm particularly impressed with the amount of Russian records of Presidium meetings and KGB notes the author was able to obtain. This leads to a lot of really great insight into the diplomatic process even between sworn enemies like the US and USSR. At seeming random, untrained newspaper editors and small businesspeople were chosen by each party to be the trusted "go-betweens" on matters relating to Cuban policy and nuclear armament. And I always appreciate historical books that contain this level of demonstrable veracity of historical events (Isabel Wilkerson should take notes).

However, the prose itself is dry and as a result of the exhaustive research, gets bogged down in recounting even the smallest of meetings. No doubt that Kennedy had dozens of meetings with his advisors on a near daily basis to figure out "what to do," but I'm not sure each one of them needed to be detailed so exhaustively. A lot of this book likely could have been trimmed simply by writing something like "In July of that year, Kennedy met over 2 dozen times with his advisors. They remained deeply split between whether to enact an embargo against Cuba or take direct military action." Instead, we get the same individuals having the same arguments in droll detail throughout. Despite the book largely centering on the back and forth between the US and USSR once the missiles reached Cuba, I actually was much more engaged by the early, leaner part of the book detailing Castro's rise to power, learning about his personality (that mirrors Tump's in many concerning ways), and how he somewhat surprisingly turned to Communism (the book notes that while Raul and Che were obvious supporters of and believers in Communism, it took Fidel awhile to get there).

Not everyone will agree with the take that the day was saved because Kennedy had no strong idea how to react to the missiles and Khruschev and the Presidium lost their nerve once the US learned about the missiles. But the level of detail of this book makes a strong case that this was indeed largely what happened. And I personally find it a bit comforting that basic humanity rather than preternatural smarts and personality saved us all.
Profile Image for Alex Hope.
82 reviews6 followers
December 10, 2021
This book is so thorough and informative. Oh my god, I loved it so much. Really, the fact that the prelude and aftermath parts take almost 100 pages each is amazing, as it gives a lot of information that might lead to conclusion that missiles were no surprise to JFK and that the mission was doomed for the Soviets all along. Such a great work for my research and a must read for everyone interested in Carribean Crisis
36 reviews
July 30, 2025
What a fascinating look into an event I vaguely remembering learning about in grade school but really had no idea about.

This book was a mammoth to read. The amount of individuals mentioned amongst all three governments was immense and hard to keep track of.

All in all, a wonderfully written account and an informative documentation of one of the most important affairs of our countries history.
12 reviews
October 26, 2022
Objectively a good book, would have enjoyed it more if I hadn’t been reading it for class. It falls into the trap of talking about Cold War leaders as if they were playing some grand chess game though, rather than being people making one (sometimes bizarre) decision at a time that almost got the world ended.
Profile Image for Felix Sun.
127 reviews
September 29, 2021
Feels a tad too long, but definitely a better (more objective) book than Robert Kennedy's 13 Days.
44 reviews1 follower
May 7, 2022
Magnificent Book

The author exposed every single fact that made the October Crisis one of the crucial moments in the modern history
206 reviews
September 25, 2025
A little more in the weeds than I was hoping for. This one's for the scholars and deep divers.
140 reviews4 followers
March 12, 2016
Another book on the Cuban Missile Crisis might seem to be overkill, but Fursenko and Naftali, the Russian and American co-authors, have delivered a terrific book that relies on newly accessible Soviet archives, and expands the period covered so we have a fuller understanding of what brought on the crisis. We have a good look at the inception of the Castro regime, with the book providing some interesting detail on the initial politics involved inside Cuba. The broader reach of the book presents us with a unique perspective, showing us the miscalculations on both sides that ultimately brought the world to the brink of war.

JFK, and Attorney General Kennedy, have always gotten well deserved great marks for the handling of the crisis, but the book shows us some errors on the U.S. side, as well as the Soviet side, in the run up towards crisis. For those looking for cheerleading this is not the book for you. The authors points to a conversation between JFK and Khrushchev son in law Aleksei Adzhubei that likely set off alarm bells in the Kremlin: JFK, in a record of the conversation in Kremlin archives, told Adzhubei a story.

"Kennedy: 'At the time I called Allen Dulles into my office and dressed him down. I told him: you should learn from the Russians. When they had difficulties in Hungary, they liquidated the conflict in three days. When they did not like things in Finland, the president of that country goes to visit the Soviet premier in Siberia and all is worked out. But you, Dulles, have never been capable of doing that.' ”

Giving the Soviets the idea that Cuba might be comparable to Hungary, and subject to U.S. invasion on the basis of "sphere of influence" politics might not have been the best idea in a conversation designed to impart the thoughts of the U.S. President in a "backchannel" conversation.

"Despite his keen interest in foreign affairs, in the spring of 1962, John Kennedy had no idea of the dangerous shifts taking place in the Kremlin’s understanding of the balance of power. He would have been surprised to learn that Khrushchev was as pessimistic about the Soviet Union’s international position as he was about that of the United States."

Khrushchev made multiple errors of his own, including buying into the concept that the United States would not detect the Cuban missile build up until it was too late to act. The book covers the fact that even back then intelligence bureaucracies would tell the powers that be what they wanted to hear.

"The Soviet Union’s chief military representative in Cuba, Major General A. A. Dementyev, raised this issue with Rodion Malinovsky before the Presidium conditionally approved the Anadyr plan. “It will be impossible to hide these missiles from American U-2s,” Dementyev warned the Soviet defense minister. The comment provoked an angry response from Malinovsky. According to Alekseev, who was sitting nearby, the defense minister kicked Dementyev under the table to register his disapproval. The defense minister, perhaps like his patron Khrushchev, clung to the thesis that U.S. intelligence would not detect the missiles until it was too late to do anything about them."

The Soviets also had to deal with an unruly Fidel Castro, who had to be pacified, politically, in the run up to the crisis, and during the crisis itself. Those interactions are covered, in some detail, in the book. They are of great interest historically, and certainly lend a greater understanding of the events leading up to the crisis, and the pressures Khrushchev faced on his side.

The movement of the U.S. Jupiters based in Turkey were in fact an integral part of the solution. The book shows us the acceptance, by JFK, of the functional equivalence of the Cuban deployment with the U.S. deployment in Turkey. The wink and nod given to the Soviet government on the ultimate removal of the U.S. Jupiters is covered, as JFK covered his political flank by not making that trade-off explicit.

Great book that brings a fuller historical understanding and wider context to the Cuban Missile crisis. It brings us all the way to Dallas, and to the removal of Khrushchev after the assassination of JFK. If this era is of interest it comes highly recommended.
Profile Image for John Melvin.
36 reviews1 follower
March 10, 2017
Unique

Unique information and points of view overcome a slightly awkward prose style and set it apart from most accounts of the Cuban Missile Crisis.
Profile Image for Işıl.
196 reviews4 followers
March 31, 2013
This book is pretty much what one should read if he ever wants to dive into the Cuban Missile Crisis and the American-Soviet Relations in general, and the fact that it is the result of a collaboration of a Russian and an American author makes it more reliable with regard to its way of depicting history.

I read this book on recommendation - a book that I probably could not have found on my own, and it reads like - dare I say it? - a novel. You got the avid actors - Kennedy, Khrushchev, and Castro in the lead as the title hints - and a quite intriguing plot to go along.

Looking at the historical value of it, you get to see how much historical awareness and the likely reaction of the public posed an important factor in Kennedy's decision-making process. Also, I didn't know there was an impulsive side of Fidel Castro. Who would have thought his inclination to recklessness nearly dragged the two major powers into a hot war. It was indeed "one hell of a gamble" that no one hesitated to raise in.
87 reviews
March 15, 2016
Excellent book, really gives a good perspective on the whole situation, and even hints on JFK's enemies and potential conspirators at the end of the book. If you think about it the Russians simply reciprocated on what the US did placing nukes in Turkey, kind of Russia's backyard. Very interesting. We were VERY close to the end.
Profile Image for Dana.
22 reviews
April 12, 2009
Pretty exciting for a history book, you almost forget that you know the outcome.
9 reviews1 follower
May 13, 2009
I don't usually like to read about history but this was really intriguing! I think it was enlightening for me to hear an inside account of how Kennedy handled this crisis as a young, new president.
61 reviews10 followers
December 15, 2013
A very descriptive account of the Cuban Missile Crisis. Though at times I felt like I was drowning in useless information, a lot of the information is relevant and new.
Profile Image for Max Price.
52 reviews
July 3, 2016
I read this as a textbook for a history class at Pacific University, and it got me hooked on the Cuban Missile Crisis. It's well-written, and the content is amazingly thorough.
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