Havana Nocturne: How the Mob Owned Cuba & Then Lost it to the Revolution

by T.J. English

In modern-day Havana, the remnants of the glamorous past are everywhere—old hotel-casinos, vintage American cars & flickering neon signs speak of a bygone era that is widely familiar & often romanticized, but little understood. In Havana Nocturne, T.J. English offers a multifaceted true tale of organized crime, political corruption, roaring nightlife, revolution & international conflict that interweaves the dual stories of the Mob in Havana & the event that would overshadow it, the Cuban Revolution.As the Cuban people labored under a violently repressive regime throughout the 50s, Mob leaders Meyer Lansky & Charles "Lucky" Luciano turned their eye to Havana. To them, Cuba was the ultimate dream, the greatest hope for the future of the US Mob in the post-Prohibition years of intensified government crackdowns. But when it came time to make their move, it was Lansky, the brilliant Jewish mobster, who reigned supreme. Having cultivated strong ties with the Cuban government & in particular the brutal dictator Fulgencio Batista, Lansky brought key mobsters to Havana to put his ambitious business plans in motion. Before long, the Mob, with Batista's corrupt government in its pocket, owned the biggest luxury hotels & casinos in Havana, launching an unprecedented tourism boom complete with the most lavish entertainment, the world's biggest celebrities, the most beautiful women & gambling galore. But their dreams collided with those of Fidel Castro, Che Guevara & others who would lead the country's disenfranchised to overthrow their corrupt government & its foreign partners—an epic cultural battle that English captures in all its sexy, decadent, ugly glory. Bringing together long-buried historical information with English's own research in Havana—including interviews with the era's key survivors—Havana Nocturne takes readers back to Cuba in the years when it was a veritable devil's playground for mob leaders. English deftly weaves together the parallel stories of the Havana Mob—featuring notorious criminals such as Santo Trafficante Jr & Albert Anastasia—& Castro's 26th of July Movement in a riveting, up-close look at how the Mob nearly attained its biggest dream in Havana—& how Fidel Castro trumped it all with the revolution. 

Genres: History, Nonfiction, True Crime, Crime, Politics, Audiobook, Book Club

420 pages, Kindle Edition

First published September 6, 2007

About the author

T.J. English's latest book is THE LAST KILO. English is an author and journalist with an emphasis on organized crime, the criminal underworld, and the criminal justice system. Many of his books have been New York Times bestsellers, including HAVANA NOCTURNE, THE SAVAGE CITY, PADDY WHACKED, and WHERE THE BODIES WERE BURIED. Four of his books have been nominated for an Edgar Award in the category of Best Fact Crime (BORN TO KILL, HAVANA NOCTURNE, THE SAVAGE CITY, WHERE THE BODIES WERE BURIED). In 2023, his book DANGEROUS RHYTHMS was given a special award by PEN Oakland. A collection of his journalism was published under the title WHITEY'S PAYBACK, an anthology that includes articles originally printed in Playboy, Newsweek, Esquire, The New York Times, and other national publications. He lives in New York City.

Reviews

[Jason Koivu · Rating 5 out of 5]

Do you like The Godfather II? Then read this and learn about the real gangsters behind the mob's 1950s invasion of Cuba.

TJ English packs in a lot of information regarding a relatively thin sliver of time, creating in Havana Nocturne the perfect time-capsule history lesson, both exciting and captivating.

English lays out the twisted web that was 1940s/50s Cuba, including the US Navy's WWII deal with Luciano that got the mobster released from prison, Cuban President Batista's friendship with the US and the mob, the CIA's assistance of the Castro/Guevara revolution against the US-backed Batista regime, and more deceitful good times!

I've had a fascination with gangsters and the mafia since first seeing the Godfather movies, which are heavily-based on real life criminals and incidents surrounding them. In Coppola's sequel, the setting shifts to the burgeoning hotel casino and club nightlife of Havana, Cuba just as it did for mob leaders like Meyer Lansky, Lucky Luciano, and Santo Trafficante. How they seized control, paid off the Cuban government and essentially overran an entire country is amazing.

With this book I got so much more than just unbelievable stories about gangsters. The people's revolt, led by the then little-known Fidel Castro, whose bumbling and poorly outfitted attempts by all rights never should have succeeded, is an incredible life-or-death fairytale. The anything-goes party atmosphere upon the island nation rival the so-called sins of Sodom and Gomorrah. The United States' tourists, wealthy businessmen and politicians like JFK throwing their money and bodies into the carnal fray, while its government looked down its nose and cried "SHAME!" is hypocritical...at best.

That any of this ever happened is astounding. The way English tells the tale is outstanding.

[Mizuki · Rating 4 out of 5]

It's a non-fictional book about the American Mafia who built an empire in Havana with drizzling tourism activities, gambling and nightclubbing business, and said Mafia's coexistence with the corrupted Cuban government.

It's also a story about how the nothing-to-lose revolutionaries eventually overturned said corrupted government and the Mafia alongside it.

Too bad that said revolutionaries eventually became a dictatorship in the end. *sighs*

After finishing this book I'd thought very long and hard about revolution. The revolutionaries could always hide in the forest after they threw bombs and destroyed proprieties, too bad things don't work this way now when people are facing suppression from evil governments.

Not to mention, this chapter of the American Mafia's conquest of Havana had been immortalized by The Godfather Part II.

The narration is very readable and interesting. Still, I must wonder why when the tour business was blossoming and casinos were opening left and right and hiring, why the majority of the population was still so poor and angry about their condition? It's worth more looking into.

[Alexander Santiago · Rating 5 out of 5]

I was always curious as to knowing more about the Mob ties to Cuba, as I knew just tidbits of info; 'Havana Nocturne' lays everything bare from the beginning to virtually that last shakened cocktail in the Mob-run casinos on that fateful New Year's Day of 1959. From Meyer Lansky, the Lower East Side kid who grew to be the brains behind the Mob muscle and brawn, and the brilliant architect of who was very close to making Havana the "Monte Carlo of the Caribbean"; President Fulgencio Batista, the dictator of Cuba who gave the go ahead to the Mob casinos on Havana - as long as he received large shares of the profits; and cast of characters who are steep in Mob lore: Lucky Luciano, Santo Trafficante, Bugsy Siegel, even the Chairman of the Board himself, Frank Sinatra, makes a guest appearance.

In addition to the Havana Mob syndicate who were intent on revamping the city, English also detailed the mores and attitudes of Havana which was quite the Sin City before Las Vegas, with very whim, predilection, vice and fantasy that could be indulged. And remember that character of "Superman" in Francis Ford Coppola's "The Godfather II"? He was a real person!! But of course, as history tells us, corrpution and a dictatorship breeds dissension, and eventually, a 'revolution' will take place, which all began with a Havana lawyer - Fidel Castro. Meticulously researched and concise, not to mention a thoroughly good read, "Havana Nocturne" almost begs to posit a 'What if . . ": if Batista had effectively squashed the Fidelistas, would Meyer have succeeded in transforming his "Pearl of the Antilles"? Makes you wonder. Highly recommended.

[Jim · Rating 4 out of 5]

This is an engagingly-told and well-researched story, the story of Havana in the 50s, a city of nightclubs, casinos, sex shows, and the Afro-Cuban jazz scene---all run by the Mob, organized mainly by Meyer Lansky, with massive payouts to Cuban dictator General Batista. Millions were there to be made with no end in sight to the partying--but, in the jungles, the forces of revolution were gathering under Fidel Castro and "Che" Guevara...

[Jill H. · Rating 4 out of 5]

My cousin loaned me this book and said "Read it, you'll like it"......I read it and I liked it.

It tells the engrossing tale of the mob and its grip on the island of Cuba under the dictatorship of Batista in the 1950s. All the usual suspects are present....Luciano, Lansky, Trafficante, et al.......as they bribe their way into positions of unrivaled power.

The glamour of the mob controlled resort casinos of that time drew tourists and "suckers" worldwide and Havana became the true Pearl of the Antilles......sex and money were the linchpins of that attraction and Cuba was "the place to go" for the rich and famous. All this at the expense of the inhabitants of the island. As history tells us, the revolution and Fidel Castro were lurking in the shadows.

It's a fascinating story of vice, corruption, and general mayhem as the revolution, so long a dream, became a reality. You may want to ask yourself the question.....is Cuba better off now than it was then? You decide. Regardless, the book will shed light on an exciting and violent period in Cuban history.

[Tom Mathews · Rating 5 out of 5]

An excellent history of the Cuban Revolution as seen through the eyes of the American mobsters who built an incredible casino industry and practically ruled a country. This is as impartial a recitation of history as you are likely to find anywhere.

[MM Suarez · Rating 5 out of 5]

An excellent non-fiction account of the Mob's hold on Cuba and the Batista government, and how the Castro revolution foiled their plans for the island. Well researched and beautifully written it reads like a novel, and it's both entertaining and informative.

[Erika Robuck · Rating 4 out of 5]

A thorough chronicle of the mafia's involvement in Cuba's history, with the profound ripple effects in all areas of life. The layers of debauchery are deeply disturbing. Fans of the Sopranos would enjoy this book.

[Steven · Rating 4 out of 5]

T.J. English combines a historian's diligence with a crime reporter's appetite for bloody gossip and revealing, sleazy anecdotes. The story of how Lucky Luciano and a cabal of American gangsters worked to turn Havana into a Caribbean Las Vegas (with the help of dictator Fulgencio Batista) has been lying around for decades, waiting to be told properly, and English has done lots of valuable spadework and original reporting. He also fits the gangsters into the political currents of the time. For those who a5re interested in the gray area where crime, business and politics overlap, this book is a must-read.

[Travis · Rating 3 out of 5]

Lots of glamor and glitz, without much depth - I feel like that description applies to both the book and its subject (1950s Havana).

The best part of the book I thought were the portions describing the early stages of the Cuban Revolution. This was very exciting and dramatic, and a story I didn’t know too much about. However, the transition from “ragtag band of outlaws in the mountains” to “the writing is on the wall and everyone knows the war is lost” happened too abruptly, and with too little color on what was happening.

The most disappointing part of the book was the story of the American mob in Havana, which is really the core storyline of the book. The problem here was just that very little happened. The exciting mob stories are all events that happened back in the US and are generally unrelated to Cuba. As far as I can tell, the story here is that underworld figures from the US paid large bribes to Cuban government officials to run the casinos, which they otherwise operated mostly as legitimate/highly profitable businesses. There are no high profile gangland killings, no wars among rival families, etc. The most significant event is the opening of a big casino (the Riviera)…

The parts of the book I disliked most were the parts that read like “travel guide to 1950s Havana”. Do I really need a rundown of the various casinos, brothels, and cabaret singers of 1950s Havana? No I do not… I also felt like the author kept repeating some variation of “Havana was all about sex, booze, drugs, and gambling” - ok, we get it, let’s just get back to the story.

I also felt the book was filled with too much exaggerations. Take the title for instance - that the mob “owned” Cuba (a notion repeated throughout the book). From what I can tell, it’s pretty clear the government officials receiving the bribes are the ones who “own” Cuba, and not the mobster/businessmen paying the bribes. And this seems confirmed when the regime changes and the mobsters are all kicked out of the country without much of a whimper….

Ultimately, the real “story” here is the Cuban Revolution, and the US mobsters’ presence is a subplot. The author tried to flip that to focus more on the mobsters, but in my opinion he just didn’t have enough story to make it work.

[Tanner Nelson · Rating 2 out of 5]

This book promised a great deal and sometimes it felt like it was going to deliver, but ultimately it lost its way and fell flat. I'm disappointed in how it ended up since I had previously suggested this book to my father for him to read in the future. But given its flaws, I'm not sure I'd recommend this read. In fact, I didn't even finish the book. I read about 4/5 of the book before finally putting it down for good.

The book ostensibly chronicles the history of the Havana mob and how the mob lost Cuba to Fidel Castro's revolutionaries. But this book is more like the literary version of a lengthy Catholic confession than it is like a history. The book gives some great history (and I learned a great deal), but then it takes enormous detours to chronicle the moral decay of Havana during the 1920s, 30s, 40s, 50s, and 60s. The first time, it fascinated me because it felt like Havana never left the Roaring 20s. But after the third or fourth litany of sins I finally grew tired of it and put the book down.

This book could be much more brief if it removed these useless chapters. The sections on "Lucky" Luciano, Meyer Lansky, Santo Trafficante Jr, Fulgencio Bautista, and Fidel Castro are great. I learned a lot about each of these men. I wish the book had stuck to its promise to chronicle how these individuals lost Cuba.

[Cara · Rating 4 out of 5]

I knew that Cuba was a "vacation spot" before Castro came to power (I recall my mom telling me her parents went there at least once) and that Batista was an "oppressive dictator" of some kind (to be fair, there are so many it's hard to keep them straight), but I didn't really know the whole story of the mob involvement in Cuba. This book fills in those details rather nicely. At the end, when Batista flees the country and the mobsters are frantically going from casino to casino to grab all their money before escaping, I almost felt bad for them. But then I am reminded that all that money came from the suffering of the Cuban people, which was glossed over in this book, but oh well, a book can't have everything. And here we are 56 years later and we Americans are still going into conniptions over the mere suggestion that we loosen the embargo on Cuba. We hate Castro because he hurt our feelings way back when and has the gall to keep on living. His human rights abuses are certainly bad, but that certainly didn't bother us when Batista was in power, nor does it bother us now when it's our allies. I could keep going with this rant, but I won't bother; it's pretty unoriginal of me.

[Bea · Rating 5 out of 5]

My interest in Cuba was kindled by a trip that I recently took there. I was struck by the many contradictions I witnessed, and I had a strong sense of a country on the verge of tremendous change. I was very curious to get a better understanding of what had led to the Revolution in the first place, rather than just looking at it as a failed social experiment.

The book details how American mobsters became the dominant economic and political power in Cuba during the 1950s. Much of this centered on the mutually beneficial relationship between lead mobster Meyer Lansky and President Batista. It helped me to see the level of corruption and exploitation perpetrated by the Americans and Cuban politicians. The book also followed the young Fidel Castro through his formative years and his rise to power.

I liked the writing style- clear, easy to follow and engaging. An excellent read for any one who wants to understand Cuba's present by understanding its past.

[Malapata · Rating 4 out of 5]

Una historia de la relación de la mafia de EEUU con Cuba, desde que Lucky Lucciano se entró de incógnito en la isla escapando de su exilio italiano hasta la irrupción de la revolución. Narrada con ritmo y trufada de anécdotas y referencias a El Padrino II, es un libro muy interesante que se lee sin pausa.

[Melina · Rating 4 out of 5]

3.75 Stars

Havana Nocturne is a comprehensive history of the American mob setting their foothold in Cuba after WW2. For approximately 15 years, they established a lucrative casino empire that ultimately collaspsed after Fidel Castro executed a successful coup of the government.

English goes into great detail by starting with the histories of the main mob players who had a vision of a casino-hotel empire in Havana. From Lucky Luciano, Meyer Lansky, and Santo Trafficante (to name a few) we learn how the delicate balance of mob power was organized, managed and sometimes was challenged in Havana. English also details the backgrounds of Bautista and Castro and provides a canvas of cultural, socio-economic and political factors that influenced their individual rise to power.

Though these personal histories are interesting, I found myself most intrigued by how the Havana tourist economy grew during this time. A unique music sound developed, the mamba, which spawned the tamer cha-cha-cha. World renown entertainers performed intimate shows that rivaled those of New York City and Las Vegas. Talented choreographers designed live shows that featured fully nude performers. Unfortunately, darker vices were also easily accessible. Live sex shows thrived in smaller clubs and prostitution was rampant.

The Havana tourist economy thrived during this short time through the will of the mob that molded the hotel casinos and the political influence they held over Cuba's president. Still, American politics and corporations held great influence and power over the country's economy. English breezes over these factors which I think is a missed opportunity in shaping the full picture of why the country's everyday people would be ready to overthrow their corrupt government.

Overall, an interesting history of the American mob and their short but influential time in Cuba.

[Joe Kraus · Rating 3 out of 5]

A couple points of preamble, I suppose. The kind of organized crime history I write is in more or less direct conflict with what English writes. I take it as an axiom that we can never genuinely know what happened among men who, literally, lied as part of their everyday professional lives. Not only that, but they often depended on those lies having currency. As I like to put it, gangsters worked to make people believe they had power and influence at the same time as they worked to keep proof of that power away from anyone who might be able to prosecute them for it. They misled everyone as a practice, so how can we hope fully to untangle the true story decades later.

As a consequence, I am always at least as interested in the footnotes of a gangster history as I am in the main text of it. As a result, then, I’m not doing this book justice since, in listening to it, I couldn’t indulge my habit of looking for (and evaluating) the quality of the source for each controversial claim. If I’d read this on paper, I might have better things to say about it…or possibly worse.

What English does here, and also in Paddy Whacked which, while never reading in full, I’ve read in often over the years, is flesh the myth of the Mafia into a larger, at least semi-documented story. He’s a storyteller, which is something I admire, but I’m not always convinced that he’s on top of the latest findings of others who – at the price of not telling their stories as smoothly – tell them more accurately and with a greater a awareness of what the sources allow us to say with confidence.

There’s a spot here early where English talks about what’s been called “The Night of the Sicilian Vespers,” a supposed wave of killings that knocked off the old time “Mustache Petes” of the Mafia in favor of the younger generation of mobsters personified by (and purportedly headed up by) Lucky Luciano. Those “Vespers” are a central part of Mafia lore and are acknowledged in FBI accounts as well as in most popular histories of the mob.

The trouble is that, as academic historian Alan Block has shown, there were no such murders. With one possible exception, there are simply no records of potential Mafiosi killed in the months following Luciano’s taking out of Joe Masseria and Salvatore Maranzano. Joe Valachi may have reported it before the McClellan Committee, but it was either hearsay or myth. It didn’t happen, and English ought to be aware of that.

Or, later, he’ll often quote Luciano’s “last testament,” a quasi-biography he dictated to reporters near the end of his life. Like Meyer Lansky’s interviews with Israeli journalists in the early 1970s, though – interviews that English cites several times – such autobiographical works were highly contextualized. Luciano was trying to interest someone in making a film about his life (and in bringing substantial rights fees with it) so he both glamorized his experiences and downplayed his own crimes. Lansky meanwhile was trying to get the Israeli government to grant him citizenship under the Law of Return that guaranteed it to any Jew who requested it. As a result, he played up his Jewish identity and worked to cast himself as someone who’d always been an outsider.

In the sort of gangster history I value, those accounts do matter, but they matter as part of the larger, contested stories in circulation about each man. They don’t tell us what happened, but they do tell us something about the way these men were trying to shape their own reputations.

To be fair, though, English has a different agenda. He has a version of organized crime history that comes out of the “great man” school. For him, the major players – Lansky above all – had a vision and went on to realize it. I don’t especially buy that Lansky scoped out the situation in the 1930s that would develop in the 1950s, but there is evidence that he did. I read it that Lansky was always looking for opportunities, that he likely explored dozens of other ventures going way back. English can’t be entirely wrong in asserting that Lansky eyed the possibility of taking over the nation of Cuba decades before it actually happened.

And English has an appealing way with words and narrative. I know firsthand how hard it is to tease a narrative out of a range of characters who are working simultaneously toward a mostly shared (but sometimes contested) end. He does a nice job of moving his story forward and then back-tracking to give the biography of some new and essential figure: Batista, Luciano, Lansky, Trafficante, and Castro. No one of those chapters is as strong as the books dedicated to each individual, but those other books don’t weave so broad a story.

In the end, I did enjoy the well-defined scope of the narrative here and, tip-of-the-hat, he even managed to dig up a detail that I wish I’d had for my own book. And that I could have had if I’d read this sooner – Chicago Jewish gangster David Yaras, with, I would claim his partner Lenny Patrick – ran the San Souci casino in the early mobbed up years. I knew that detail, though the FBI gives them a different Mafia partner (Detroit’s Joe Massei according to the FBI, Pittsburgh’s Sam Mannarino here), but I wish I’d known this claim that Yaras was part of first wave of short-sighted thugs as opposed to the subtler, long-term thinking of Lansky and his crew.

So, if you’re curious about this era of Cuba – and it’s often fascinating for the way it helped invent a music and a style that defined much of the era – and if you’re not as hung up on the footnotes as I am, there’s a lot here to enjoy.

[Sherri · Rating 5 out of 5]

This was so good!

[Maphead · Rating 4 out of 5]

Must have been good because I couldn't put it down.

[Pete daPixie · Rating 3 out of 5]

A fairly comprehensive history of twentieth century Cuba and the infiltration of organised crime into the island that ended with the revolution of Fidel Castro in 1959. Written chronologically in essays of around twenty page chapters, the author utilises many previous publications as well as first hand interviews to produce a coherent and well written documentary of 'The Havana Mob'.(2007)
The principal players of 'Lucky' Luciano, Meyer Lansky and Santo Trafficante with a full supporting cast of Mafiosi, aided and abetted by dictator Fulgencio Batista laid the world's biggest golden egg, only for Fidel, Raul and Che to achieve in weeks what Hoover's FBI along with other U.S. agencies had failed to do over decades and hole the underworld operations below the waterline. Full of fascinating anecdotes and exposure of involvement in the Havana high life of such as Frank "Any report that I fraternise with goons and racketeers is a vicious lie" Sinatra. A playground of sea, sand and sex for the rich and famous in the plush casinos, hotels and erotic hot spots that turned Cuba's capital into a Sodom and Gommorah.
Sadly, the name of Jack Ruby is not mentioned in the cast list, although his associate Lewis McWillie is covered. Ruby's sojourns to Havana to visit McWillie and his reported visits to Trafficante during the Dons incarceration in Triscornia seem odd omissions.
There are many ironies in the detail of Mr English's text. I had to smile when learning of Meyer Lansky's estate when he died in 1983 was just 57,000 dollars.
Now the labour leader's screamin'
When they close the missile plants
United Fruit screams at the Cuban shore
Call it peace, or call it treason
Call it love, or call it reason
But I ain't marching anymore!

[Erik Graff · Rating 4 out of 5]

A year ago my roommate's mother came on her annual visit with an interesting-looking book about the Mafia in Cuba. This year she returned with the book in hand, intending to leave it with us.

Havana Nocturne traces Cuban history in terms of the Mob from the twenties through the revolution in 1959 to the assassination of President Kennedy in 1963. The focus, however, is on 12/1946, the organized crime planning conference at Havana's Hotel Nacional, to early 1959, when the gangsters were thrown out of the country and their properties--clubs, hotels and casinos--were expropriated.

The author, who specializes in crime history, writes accessibly and informally--sometimes too informally for my tastes, concerned as I am with the documented historicity of what I'm reading. Material from published sources is supplemented by interviews with some surviving principals. While there is irony throughout and parts are positively funny, the whole picture is an ugly one, the author's thesis being that 1946-59 represented a period in which organized crime virtually took over a government for its own purposes.

In this story few come across favorably. In addition to the dictator, Batista, and his thugs, the Mafia leadership and their thugs, there is an array of the rich, powerful and famous who benefitted, a list which includes the PanAm and Hilton corporations, U.S. ambassadors, Senator Jack Kennedy, Frank Sinatra, numerous film actors, stage performers and, of course, lawyers and their firms. If there are any heroes in this book they are the Castro brothers, Che Guevara and all those other Cubans who conducted the virtually bloodless overthrow of the kleptocracy.

[Stephen · Rating 4 out of 5]

I used to be obsessed with la cosa nostra, but its Cuban ambitions never popped on my radar until I watched The Godfather II. I’ve long been curious about the Mafia’s role in developing Cuba and inadvertently feeding the revolution that swapped out one dictator for another, but not until recently did I come across this book. I went for it it immediately, teasing me as it did with the promise of information as to how Lucky Luciano and the Syndicate helped the Allies in World War 2. As it happens, that WW2 connection is marginal at best, but this is still the fascinating story of how the Italian-American Mafia began building Cuba up as an off-shore power base, only to lose everything to a rich boy turned revolutionary. (Odd how left-wing dictators are so often the children of privilege and right-wing dictators begin as poor populists, Stalin being an exception.)

The story of the Mafia and Cuba begins with the close friendship of Meyer Lansky and Charles “Lucky” Luciano, two men who revolutionized organized crime in the United States. As his last name might hint, Lansky was no Siciliano; he was, instead, the son of Polish Jews who’d fled pogroms in Russia to come to the United States. Meyer, despite his small stature, was cunning and ambitious, and as he aged he joined forces with similarly ambitious men like Luciano: “Lucky” would conspire to knock off the heads of the two largest Mafia families in New York, Massiera and Marazano, and create something new: the Syndicate, modeled on corporation-esque lines. Lansky, a man whose fortune grew on gambling operations, saw in Cuba an opportunity for expansion — but his dreams continued to be deferred, first by economic depression and then by the incarceration of Luciano. The Syndicate wasn’t as ethnically closed-off as the traditional Sicilian Mafia, but it still wasn’t going to let some “little Jew” dictate policy: for that, Lansky needed his buddy Charlie, who despite his imprisonment and later exile remained the de facto CEO of the syndicate. Luciano legally escaped prison by using the muscle of the Mafia to rout German saboteurs on the New York waterfront, then later supplied information to help the Allies invade Sicily; then, pushing his luck, he decided to emigrate to Cuba to begin realizing his and Lansky’s dream of a gamblers’ paradise in the Caribbean.

Cuba was enormously popular with Americans, both for the climate and the emerging Afro-Caribbean musical scene. Capitalizing on the amount of traffic already coming in by creating new entertainment venues to suck up tourist dollars was a no brainer. This was accomplished through both the mob’s existing money and Lansky’s longstanding contact with a certain Batista, the on-again off-again ruler of Cuba. The timing couldn’t be better, since American lawmen were taking an inconvenient hard line against gambling operations in the States. As it happened, Lansky and Co.’s desire to make big moves in Cuba coincided with Batista returning to power — this time as a coup disguised as a pre counter-coup. Although Luciano wouldn’t be part of it, DC having pressured the prior government to deport him back to Italy, the door was already open to Mafia investment. Soon financial institutions were in place that bought Cuba’s government and Syndicate money into full collusion, even as resentment to Batista’s bare-faced power grab brewed on the streets. The disparity between those in power and those not grew ever larger as casinos and nightclubs — the latter hotbeds of license, libertinism, and outright depravity — became gathering places for both Batista’s people and those connected to the Syndicate. Big names from the United States, including Sinatra and JFK, especially enjoyed the fleshpots. With firebrands like Castro in jail, though, and business booming, all seemed well.

Unfortunately for the mob’s ever-expanding array of hotels, clubs, and one-armed bandits, Batista got a little too cocky. He released the Castros from prison, and they fled the country to foment revolution in Mexico the way Khomeini worked from France during his own exile from Iran. Castro’s attempt to stage a comeback was at first a dismal failure — he and his men returning by boat were delayed by bad weather that failed to sink him, and his men in place in Cuba were slaughtered by Batista’s army. Upon finally landing, Castro linked up with his remaining men and continued to meet defeat after defeat, until Batista unwittingly declared him dead when in fact he was merely in hiding. Castro and his followers began rebuilding their numbers, importing weapons, and antagonizing the government through petty actions like raiding banks and setting things on fire. Disaffection towards Batista continued to grow even wealth flowed into the island: Lansky was actively planning Havana’s largest, most entertainment-oriented resort yet when the bottom fell out. Although some of the mafiosi were aware of Castro’s rising influence, they dismissed it: even if he did take over, he wouldn’t be so stupid as to close the casinos. Then, on New Years Eve, Meyer Lansky was told that Batista had taken money and run: Castro was on his way to claim Havana. Although Lansky scrambled to tell the Syndicate’s casinos to get their money out of the country, the people on the ground were slow to move, and soon Castro was actively working on undermining Cuba’s tourist-based economy by closing the casinos and nationalizing the hotels. Although some wealth managed to escape the country, the principal investors were largely ruined: Lansky died with less than $50,000 in the bank.

This was a fascinating history on two levels, both in providing a very cursory introduction to Castro’s takeover, and in diving into how the Mob had worked its way into so much of Cuba’s government and financial sectors. Thinking about what might have happened had Castro and his inner circle died at sea during the beginning of the “July 26 Movement” — as they very nearly did — is tantalizing. Imagine no Cuban Missile Crisis, a redoubt for the Mob after RICO hits, a Caribbean war between wiseguys and Escobar’s organization! It appears the author has written a lot on gangs of the 20th century, including Irish gangs, so I may read more of him: he may be a modern Herbert Asbury.

Related:
The Little Man, biography of Meyer Lansky. Later released as The Thinking Man’s Gangster.

[Clif · Rating 5 out of 5]

Havana Nocturne is a delightful read. It has adventure, revolution, violence, murder, sex, movie stars, the Mob, lavish entertainment, an exotic locale, JFK and Frank Sinatra!

And it's all true.

The book is based on the rise and fall of reclusive Meyer Lansky. Lansky, like many mobsters, came from a squalid youth in a poor section of NYC and found wealth addicting. No scheme was too grand, no hotel large enough. In pre-Castro Cuba it looked like the whole place could be owned what with the corrupt Batista in charge. Unlike many mobsters, Lansky preferred to manage the show rather than be in it. He held on to power because he was respected for his ability to turn ill-gotten gains into bricks and mortar.

His projects flowered and Americans poured south to experience the high life, see the stars and indulge in the kinky if so inclined. Lansky's magic touch made his dreams and those of many others come true...with the notable exception of the mass of Cuban people.

Than came a man with a beard to take it all away.

If you are a fast reader you might be able to read this book in two days, but however long it takes you, you will enjoy it.

[Alex · Rating 2 out of 5]

I was looking forward to getting deep into the Cuban experience with the mob in the 50s. But more than that the tie into the revolution and how the mob navigated the Castro regime as it pulled Batista out of power. The book gets very deep into the mobster interaction, relationships, and just gossip. This is at the expense of a true telling of the history. You don’t get an appreciation for the interplay of events from the revolutionaries, the mob, and then the government. Sure it’s covered but there’s so much back-and-forth that it’s hard to get a dense appreciation. The timelines are fluid. There is no sense of continuity at all.

Bottom line is that there are better books about Cuba during the tumultuous time. There are better books about the mob. This is full of hearsay in urban legend and at nearly 400 pages it’s just not worth the investment.

[Alissa Thorne · Rating 5 out of 5]

Mobsters and hookers and spies, oh my!

A compelling and mind boggling tale of hedonistic paradise hand crafted by gangsters in the city of Havana, Cuba and later seized and crushed by Castro[1]. This historical account alternates from the lives of powerful leaders of organized crime in the era, to the big picture influences of their actions on culture and history. It's possible that a true history buff would find this somewhat lacking in detail, as the style had more of an emphasis on storytelling than education. But what a great story it was.


[1] The author has an undeniable pro-Castro bent. I didn't find this to get in, the way of a great story, nor of me forming my own interpretations of events.

[Harry Weber · Rating 2 out of 5]

def. not my cup of tea.

the story might be interesting and i'm sure it would've been an excellent read (in a different book) but it wasn't. and this solely owned to the appallingly boring schoolkid-renarration-style english chooses to use.

maybe it's just me, but if i want to read a plain, dry chronicle of the sequence of events i'll read a book on history.

and to Rosh (the guy who recommended this book strongly; advocated it: mate, if u want to have a thrilling cuba novel w partially the same events (ok, not so much mob in there), but written in a style that doesn't drop u bored to death after three pages: go read Stephen Hunter's "Havana", which knocked me off the socks)

[Melinda Elizabeth · Rating 3 out of 5]

The Havana Mob and their business interests in Cuba is an interesting glimpse into a time long gone. Focusing on some of the less public mobsters (such as Meyer Lansky), the novel takes us through the late 40's and 50's as the Mob ran some profitable rackets out of Havana.

Well detailed and paced, the book provides enough of the legal and political components to give a good background to the rising revolution soon to hit Cuba, and enough Mob gossip to make it a very interesting read.

[Cristobal · Rating 4 out of 5]

A fascinating look at the postwar history of Cuba and how thanks to an incredibly corrupt government the US mob started a plan to convert the island into its international center of operations. Interlaced with a brief history of the nascent revolutionary movement that would end up thwarting the mob's advance, the book's writing gives a great overview of the unseen forces that also allowed the revolution to triumph and how its consequences would reverberate in the US.

[Sam · Rating 5 out of 5]

Lot of books on Cuba focus on Castro's point of view and or it starts from the revolution take over (July 26th). We are typically given a brief summary of Batista but not as in depth as this goes. This does a good job of what led up to that moment and why the people were fed up. Some parts I could have done without like the history on some of the showgirls but all in all I would recommend it

[Susan · Rating 2 out of 5]

I read this book because Rick had read it and it was here. I prefer to get my history lesson through historical fiction :)

[Brenda · Rating 2 out of 5]

This was a Work Book Club selection. It really wasn’t my cup of tea subject-wise. But I know I could now run the ‘1959 Cuban Mob’ category on Jeopardy. 🙃