Things are not going well for Ruby’s Singapore Supper Club, and in desperation he changes the club’s name to the Silver Spur Club and turns it into a country and western dance hall that serves only beer and “setups.” The swank Singapore Supper Club has sunk to the level of a common beer joint.

Ruby also is having trouble with the Texas Liquor Control Board and the Dallas Police Department. In 1951, he is charged with serving alcohol after hours. He is fined and forced to close at 10:30 instead of the 12:00 closing time required by law. The penalty is for 30 days, which puts even more financial stress on the club’s operation.

Ruby thinks being a Jew is causing his problems with the law. Late one night when Ruby goes to Webb’s Coffee Shop, he runs into a fellow club manager named Lewis McWillie. Ruby doesn’t know McWillie but has seen him at the Top of the Hill Club that McWillie manages. Ruby introduces himself and engages McWillie in conversation. Ruby laments the fact that the police are harassing his Silver Spur Club because he is Jewish. McWillie is sympathetic with Ruby and suggests that he go and see an influential Jewish businessman named Julius Schepps.

A few days later, Ruby does indeed arrange a meeting with Schepps. Ruby explains his situation to Schepps, who promises to look into the matter. Schepps obviously is a man of his word. Police harassment of Ruby stops immediately. Ruby is forever indebted to both Schepps and McWillie. He becomes McWillie’s lifelong friend.

1 country western

Ruby changes the Singapore from a supper club to a country and western dance hall under a new name, the Silver Spur.

But Ruby is still in serious financial trouble. He tries all sorts of things to earn money. While still operating the Silver Spur Club, Ruby sells costume jewelry at discount prices. At the 1951 State Fair of Texas, he sells sewing machine attachments. He goes in with a local man named Jim Harris in running parking lots for the State Fair and college football games at the Cotton Bowl. It was Harris who suggested to Ruby that a country and western dance hall would be more popular in Dallas than a foo-foo supper club, leading Ruby to change the Singapore name.

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To try to earn extra money, Ruby sells sewing machine attachments at the 1951 State Fair of Texas.

Ruby is terrible at managing his employees. He bullies them with threats and intimidation, tries to cheat them out of their pay and delays paying them. He has a quick temper and sometimes resorts to violence. Once in 1950 at the Silver Spur Club, Ruby hits one of his bartenders in the head with a blackjack. A year later, he gets into an argument with guitarist Willis Dickerson, who tells Ruby to “go to hell.” Ruby knocks Dickerson down, then pins him to a wall and kicks him in the groin. During the brawl, Dickerson bites off part of Ruby’s left index finger.

Ruby is even worse at managing his money. His financial records are a total wreck. He’s always late filing tax returns, paying rent, and meeting his payroll. The Silver Spur Club is on the verge of financial collapse. So what does Ruby do? He buys a second club.

In February, 1952, Ruby borrows $3,700 from a friend, Ralph Paul, to purchase the Bob Wills Ranch House in partnership with Martin Gimpel, a former associate in the Spartan Novelty Company in Chicago. Like the Silver Spur, it’s a country and western club. It will be a short-lived venture.

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In 1952, Ruby buys the Bob Wills Ranch House in partnership with Martin Gimpel.

With two establishments to run, Ruby has twice the financial headaches. In April, 1952, he is forced to abandon his interest in the Ranch House and in July, 1952, transfers the Silver Spur Club to Gimpel and Willie Epstein. Ruby is disappointed, disillusioned and desperate. He is broke; he owes back taxes to the IRS; he is living in a room at the YMCA; he has no prospects for the future. He disappears. He is not seen in Dallas from August to November, 1952. The Warren Commission thinks he’s in Chicago. Actually, he’s in Florida, learning the basics of the gun-running business.

Jack Ruby Meets Fidel Castro.

On March 10, 1952, Cuban General Fulgencio Batista stages a coup d’etat, ousting Cuban President Carlos Prio Socarras and taking control of Cuba. Prio is a very wealthy man (a fortune estimated at $50 million, most of which was stolen from the Cuban treasury). After the coup, he flees Cuba, goes to Florida and begins plotting his return to power. A number of groups in Cuba are planning counter-revolutions to unseat Batista, and Prio is trying to decide which one to back. One of the most vocal groups is led by a charismatic young lawyer named Fidel Castro.

Prio knows that Castro is friends with mobster Santo Trafficante, Jr., who had been dispatched to Cuba in 1946 by his father, Tampa mob boss Santo Trafficante, Sr., to oversee operations in Havana. The younger Trafficante speaks Spanish fluently which gives him a tremendous advantage over other mobsters from the U.S. Castro is a student at the University of Havana at this time. He’s also on an amateur baseball team where he meets Trafficante. The two young men become friends who often pal around together.

In July, 1952, Prio contacts Trafficante who has come to Miami on an unrelated business matter. Prio wants Trafficante’s help in fighting Batista. At this point, Batista is an unknown quantity, so Trafficante hedges his bets and initially cooperates with Prio. Trafficante contacts Dave Yaras, a mobster from Chicago who is in and out of Cuba on business for mob boss Sam Giancana. Yaras, coincidentally, is a childhood friend of Jack Ruby.

As it so happens, Yaras is on his way back to Chicago. Late in July, 1952, he stops in Miami to meet with Trafficante and Prio, then goes on to Chicago.

Sometime early in August, 1952, Jack Ruby shows up at Yaras’ door. Ruby is down on his luck, big time. Against his better judgement, Yaras holds out the possibility of working with Ruby on the deal that’s brewing in Cuba. It involves the illegal sale of firearms to Cuban rebels.

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On March 10, 1952, Fulgencio Batista (R) overthrows the government of Cuba, forcing President Carlos Prio Socarras to flee to Miami.

Dave Yaras puts Ruby in touch with a gun-smuggler in Florida named Donald Edward Browder. Unbeknownst to Yaras, Browder also happens to be a C.I.A. operative.

In September, 1952, Ruby goes to Daytona, Florida, to see Browder who gives Ruby a crash course in gun running. He tells Ruby that the world is awash in guns following World War II, and that there are more revolutions brewing in the Caribbean and Central America than he can handle, so he welcomes the help. He tells Ruby that smuggling guns can be very lucrative, but also dangerous. Ruby is thrilled. The thought of making good money while doing something exciting appeals to him. He goes all in.

Browder takes Ruby with him to meet Carlos Prio in Miami, Florida, sometime around mid-September, 1952. At this point, resistance groups in Cuba are fragmented and poorly organized. Prio believes he can use Castro to start a resistance movement. Browder schedules a trip to Santiago, Cuba, for a secret meeting with Fidel Castro and an American named Robert McKeown, a friend of Prio’s who runs a business in Santiago. Browder takes Ruby with him.

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Ruby goes to Miami to meet with Carlos Prio about his new gun-smuggling venture in Cuba.

Browder hires a pilot named Joe Marrs, owner of Marrs Aircraft in Miami, to fly them to Cuba. Marrs is an experienced smuggler who knows how to get in and out of the U.S. undetected. In late September, 1952, Marrs flies Ruby and Browder to Santiago. Waiting for them at a private airport in a ‘48 Lincoln Continental are Fidel Castro and his brother, Raul.

There is an instant connection between Castro and Ruby. At 6’2”, Castro towers over the 5’8” Ruby. Jack is awe-struck. Although Castro speaks broken English, Ruby hangs on every word. He is captivated. Castro is well dressed, well groomed and distinguished looking. Ruby thinks Castro is a very classy guy.

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There is an instant connection between Ruby and Castro. Ruby thinks Castro is a classy guy.

Castro drives them to Robert McKeown’s office on the outskirts of Santiago where they have a 4-hour meeting. Castro explains that he needs guns and ammunition, but he has very little money. Browder broaches the subject of getting money from Carlos Prio, but Castro will have none of it. Castro loathes Prio almost as much as he detests Batista. Browder tells Castro that they can’t do business without money up front. Castro says he’ll get the money and pay on delivery. Browder won’t do it, but McKeown and Ruby agree to work with Castro. That earns both men Castro’s tremendous gratitude.

As soon as they return to the U.S., Ruby heads back to Chicago where he contacts Dave Yaras. If you’re looking to buy illegal guns, there’s no better place than the streets of Chicago.

Yaras provides Ruby with 200 handguns and 30 hunting rifles for $2,500 cash, money put up by Robert McKeown. Yaras tells Ruby that, if he wants military grade weapons, he should go see Carlos Marcello in New Orleans.

Ruby stashes the guns in cardboard boxes in the trunk and backseat of his car and drives nearly 2,000 miles to Miami. It takes him almost three days. He vows to find a source of guns closer to Miami.

As soon as he gets to Miami, they load the guns aboard Marrs’ Cessna 172 at midnight and take off on a five-hour flight to Santiago. It is Halloween morning, 1952, when they arrive in Santiago. Raul Castro and two friends are waiting. Ruby is disappointed that Fidel Castro isn’t there, but Fidel is busy elsewhere. Fidel has spent the evening in Havana with the beautiful young socialite, Natalia (Naty) Revuelta, while her husband is at a medical conference in Mexico City. Naty is sympathetic to Fidel’s cause and will provide some of the funding for his weapons.

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Joe Marrs of Miami, Florida, uses his Cessna 172 to smuggle guns into Cuba with Jack Ruby.

After Raul and his friends inspect the weapons, Raul hands Ruby an envelope with six-thousand U.S. dollars in cash. They load the guns on a large truck, cover them with sugar cane, shake hands and drive away. Similar scenes will be repeated more than a dozen times over the next six years.

Ruby walks away with a cool $1,500 profit, money he desperately needs. He could use more deals like this. On the way back to Dallas, Ruby stops in New Orleans to see Carlos Marcello. The only reason Marcello will even talk to Ruby is because Dave Yaras has vouched for him.

Actually, Carlos Marcello doesn’t meet with Ruby. Marcello almost never does business in person. He has his associates do his bidding. That’s one way to avoid prison. Ruby meets with a low-level goomba named Frenchy Brouillette. Frenchy is a good-natured cajun who does a lot of grunt work for Marcello’s mob. He meets with Ruby at Katz ‘n Jammer Bar on Camp Street in the French Quarter. Basically, Frenchy tells Ruby that they can supply just about any type of military ordnance or equipment they need and ship just about anywhere in the Caribbean or Central America. They use their large fleet of shrimp boats, since they draw a lot less attention from U.S. Customs and Coast Guard.

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On the way back to Dallas from Miami, Ruby stops in New Orleans to meet with Frenchy Brouillette who works for Carlos Marcello.

Ruby is elated when he leaves New Orleans to head back to Dallas. Finally, his luck may be turning. He’s found a convenient source of guns and a way to deliver them. All he has to do is wait for the revolution to begin. It will be a gold mine, he thinks.

Let the Fiasco Begin.

Like everything in Ruby’s life, the Cuban revolution doesn’t work out quite as planned. It turns out to be a battle of wits between a charismatic buffoon (Castro) and a pompous moron (Batista). On July 26, 1953, Fidel Castro leads a force of 123 poorly trained student rebels in a raid on the second largest military base in Cuba filled with 800 crack troops armed with the latest weapons from the U.S. military arsenal. Any fool could have predicted the outcome of this battle.

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Castro’s attack on the Moncada Barracks turns into a bloodbath. All his fighters are killed or captured.

Eight of Fidel’s fighters are killed in the battle. Eighty others are captured, tortured and executed. Fidel, Raul and the remainder of his force run away and hide but are captured a few days later. They are all put on trial, convicted and given lengthy prison sentences. They won’t be needing any guns from Jack Ruby for a long time.

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Fidel Castro’s failed revolution in July, 1953, is a major financial setback for Jack Ruby.

Meanwhile, back in Dallas, Jack Ruby is still struggling to make a living in the club business. In January, 1953, Ruby reopens the Silver Spur Club, and just as it had done earlier, it barely breaks even financially. And just as he had done before, Ruby adds a second club to his portfolio of under-performing properties. He finds a new partner named Joe Bonds, and in March, 1953, they buy the Vegas Club from a rival club owner, Abe Weinstein.

All this is playing out amid the backdrop of yet another shameful era in American history. The “red scare” and McCarthyism that emerged at the end of World War II reaches its zenith in the early 1950s. While McCarthyism is hardly on par with America’s past sins of genocide, slavery and internment, it is nonetheless an ugly wart on Miss Liberty’s face. Jack Ruby’s problems seem trivial when compared to the drama unfolding in Washington D.C. at the time. And somehow, Ruby is involved, albeit probably at a very low level.

On May 6, 1953, Jack Ruby is in Washington D.C., hobnobbing with anti-communists Vice-President Richard Nixon and wealthy businessman Prescott Bush (George Bush’s father and former Nazi sympathizer). What is Ruby doing in the company of these two guys? Is this a carry-over from Ruby’s time in the military when he supposedly spies on communist party meetings in Muncie, Indiana? Is Ruby still working for Richard Nixon as he was back in 1947 while Nixon was battling communism as a member of the House Un-American Activities Committee? Whatever the case, it doesn’t seem to be helping Ruby financially.

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The mad-hatters club? Prescott Bush adjusts Richard Nixon’s panama hat as Jack Ruby looks on.

Back in Dallas, the Vegas Club still is in the red, and Jack Ruby doesn’t have the money to keep it going. In July, 1953, Ruby and Bonds bring in a new investor, Irving Alkana, but the club continues to perform poorly. That same month, Ruby learns about Castro’s failed attack on the Moncada Barracks in Cuba. Poor Ruby just can’t seem to get a break.

In September, 1953, Alkana takes over management of the Vegas Club, but it continues to lose money. He finally gets fed up and returns his interest to Ruby on June 19, 1954. Ruby is left to manage the club on his own because his partner, Joe Bonds, gets convicted of sodomy and sent to prison for eight years.

Desperate for money again, Ruby takes a shot at everything that comes along. He tries selling pizza crusts to Dallas restaurants; he tries selling an arthritic preparation; he manufactures and markets a liquid vitamin formula. He even dabbles in talent management with a young man named “Little Daddy” Nelson, but legal entanglements involving Little Daddy’s mother prove too difficult to overcome, so he abandons the project.

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Jack tries selling an arthritic preparation. He also tries his hand at talent management with a young man named “Little Daddy” Nelson. Neither is successful.

Early in 1954, some of the guns used by Fidel Castro in the Moncada Barracks attack in Cuba are traced back to their origin: Jack Ruby, et al. In May, 1954, the United States indicts former Cuban President Carlos Prio, Joe Marrs and Robert McKeown on charges of illegally exporting arms to Cuba. Prio pleads no contest and receives a small fine. Marrs and McKeown are convicted and receive probated sentences. Because of Don Browder’s connection with the C.I.A., he isn’t charged or indicted. Neither is Jack Ruby.

It seems like Ruby is getting preferential treatment. Someone high up in government is protecting him for some reason. What’s surprising is that it’s happening at a time when anti-semitism is running high because of the Julius and Ethel Rosenberg case. The Rosenbergs are a Jewish couple convicted of spying for and supplying nuclear bomb secrets to the Soviet Union in 1951. They are executed by electric chair on June 19, 1953. (It will later be discovered that the “secrets” Julius Rosenberg gave to the Russians was information they already had.)

Ruby may not have to worry about getting the chair, but he does have other problems in the form of Federal taxes he owes the government. It seems as though Ruby is constantly scrounging for money, in spite of the cash he earns from gun smuggling and from being a paid spy for Nixon (although, exactly who he is spying on isn’t clear). Ruby receives some financial relief with a loan from his brother Sam Ruby who sells his interest in Earl Products and moves to Dallas in June, 1955. Sam loans Jack the $5,500 he needs to pay excise taxes on the Vegas Club. As security for the loan, Sam requires Jack to execute a bill of sale on the Vegas. If Jack defaults, his brother gets the Vegas Club. This puts even more pressure on Jack

But one thing is working in Ruby’s favor. A month earlier, in May, 1955, Fulgencio Batista makes a colossal mistake. He releases Fidel and Raul Castro from prison as part of a general amnesty for political prisoners. Fidel and Raul both move to Mexico where they meet Che Guevara and begin plotting the overthrow of the Batista government.

One night in September, 1955, Robert McKeown comes to see Jack Ruby at the Vegas Club. McKeown is on his way from Houston to Kansas City, but stops off in Dallas to give Ruby a message. Castro’s revolution is back on. Ruby is excited. As usual, he’s hurting for money and needs this to happen as soon as possible. Unfortunately, it doesn’t. It will be months before he hears from Castro again.

Meanwhile, Ruby defaults on the loan from Sam Ruby, and a nasty lawsuit between the brothers ensues.

While Ruby is embroiled in a spat with his brother Sam, Fidel Castro and his brother Raul are pacing around their cell in a Mexico City jail. The Castro brothers, along with Che Guevara, are cell mates. They all have been arrested for weapons violations in Mexico. They have been buying and storing weapons in preparation for their return to Cuba. Their arrest and loss of guns delays their invasion plans.

When Castro gets out of jail in July, 1956, he receives a coded message from Carlos Prio. He wants to meet with Castro in McAllen, Texas, to determine how they can work together in overthrowing Batista.

In August, 1956, Fidel Castro swims across the Rio Grande and meets with Prio who gives him $100,000 to buy guns and equipment for his fighters. Castro earlier had vowed never to work with Prio, but his attitude has changed considerably at this point. Castro immediately contacts Robert McKeown, who in turn, sends a message to Jack Ruby. McKeown is still on probation for his role in the Moncada Barracks gun sale in 1953, so he only sends coded messages by a trusted courier.

Ruby goes to see McKeown who has been deported from Cuba and is now living in Kemah, Texas, south of Houston. From there, Ruby drives to New Orleans to meet with Frenchy Brouillette to order Castro’s guns. Ruby is carrying $20,000 in cash.

Jack Ruby Meets Celia Sanchez

At 3:15 a.m., on November 20, 1956, a 50-foot military surplus cargo boat is slowly making its way down the dark shoreline along an isolated beach west of Santiago, Cuba. Jack Ruby and Robert McKeown are peering at the shore looking for a signal light. After nearly 30 minutes of trolling back and forth along the shore, they see a flashing light. They return the signal with their light. They receive the final signal that it’s safe to come ashore.

The boat turns toward the shore, reduces speed and slowly drifts toward the lights from a truck parked on the beach. When the boat reaches the beach, Ruby and McKeown can see the silhouettes of several people waiting by the parked trucks. Ruby and McKeown disembark and wade ashore. They are surprised to hear a woman’s voice.

“Welcome to Cuba,” says Celia Sanchez in the raspy voice of a chain smoker. “El Comandante wishes he could be here to greet you in person,” Celia goes on to say. “But he will arrive very soon.”

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Jack Ruby and Robert McKeown arrive in Cuba with a boat full of arms for the revolution. They are surprised to be greeted by a woman, Celia Sanchez. She turns out to be the brains behind the revolution.

Neither Ruby nor McKeown know Castro’s schedule. All they know is that they are to deliver guns and ammo to a beach in Cuba, and they have accomplished their mission. Ruby’s cut will be nearly $2,500.

Fidel Castro will not be arriving for nearly two weeks, and his landing will not be quite as uneventful.

On November 30, 1956, Ruby returns to Dallas in high spirits. He’s got money in his pocket again, cash money that no one know about, not even the I.R.S. But a few days later, he’s back in the doldrums.

On December 3, Ruby wakes up to the news of Castro’s invasion of Cuba, and the first reports of the fighting aren’t good. Fidel Castro is dead!

Rumors of His Death Are Greatly Exaggerated.

Fortunately for Ruby — and Castro — news of Fidel’s death is premature. Although most of Castro’s invading force is killed or captured when they invade on December 2, 1956, Fidel, Raul and Che Guevara manage to escape. It takes them nearly five days, but they finally make it to the San Maestra mountains east of the landing site where they link up with Celia Sanchez, the real brains of the Cuban revolution. Celia has the weapons Jack Ruby delivered, plus a small army she has recruited. She has even begun training the troops with the help of Camilo Cienfuego. All Castro has to do is march in and take over, which he does.

When Castro reaches the San Maestra Mountains, he meets up with Celia Sanchez, who has everything ready to go. All Castro has to do is walk in and take over, which he does.

Ruby doesn’t learn Castro is still alive until February 24, 1957, when the New York Times breaks the story. Ruby’s golden goose has risen from the dead. As usual, Jack can use some good news. He’s operating three clubs, The Vegas, the Silver Spur and Hernando’s Hideaway, and none of them is making money. He’s also having trouble with his liquor license and his ongoing problems with the I.R.S.

By the middle of 1957, Castro’s rebel army numbers about 300. From their base in the San Maestra mountains, they are waging a successful guerilla campaign against Batista’s government troops. Once again, Browder and Ruby begin to smuggle guns from Florida and Texas to Castro. Little do they know that their activities are being monitored by both the C.I.A. and U.S. Customs.

As the war continues, Castro and his growing number of rebels need more and more weapons. For much of 1957 and 1958, Ruby commutes between Dallas and Kemah on Galveston Bay. Ruby and McKeown store guns and ammunition in a two-story house between the waterfront and railroad tracks in Kemah, and on the weekends they load guns onto McKeown’s 50-foot long boat and set sail for Cuba.

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Ruby commutes between Dallas and Kemah, Texas, where he and Robert McKeown depart for Cuba with guns and ammunition for Castro’s rebels.

Both Ruby and McKeown begin to develop a strong bond with Castro. They become so close that, shortly after Castro takes over in Cuba, he flies to Houston to meet with McKeown in an attempt to persuade his good friend to return to Cuba. Castro promises McKeown a high government position or a business concession.

He doesn’t make the same promise to Ruby. Castro knows Ruby’s secret. Ruby is a C.I.A. informant. He has been since 1947 when he was hired by Richard Nixon to spy for his HUAC hearings. Castro wants Ruby to remain in the U.S. where he can feed misinformation to the C.I.A., and also unknowingly provide important information to Castro. Without his knowledge or consent, Ruby has become part of the amazing spy network Castro uses to stay in power for the next 60 years. All Castro has to do is dangle money in front of Ruby, and he owns him.

Castro not only fools Ruby, he tricks the C.I.A., as well. They have no idea Castro is using Ruby, and they continue to protect Ruby and his gun-running activities. Unlike McKeown, Carlos Prio and dozens of other people who supplied arms to Castro, Jack Ruby is never charged, indicted or even questioned by the U.S. government. The F.B.I. has a 1000-page file on Donald Browder, but they release only three pages to the Warren Commission. For some reason, the F.B.I. conceals their information about Ruby’s gun-running activities entirely, as does the Warren Commission, the House Select Committee on Assassinations, and the Church Committee.

The gun-running business is so good that Ruby starts to branch out. He buys an interest in two aircraft that he uses to illegally transport arms unopposed by either the C.I.A. or U.S. Customs. Ruby is flying high.

Farewell to Arms

Then as suddenly as it all began, it abruptly ends. On January 1, 1959, Fidel Castro and his rebels succeed in overthrowing Batista. There is no need for Ruby to continue supplying arms and munitions to Castro. But concerns over political conditions in Cuba begin to surface, and they do not appear to be in the best interests of the U.S.A.

Within months after Castro’s takeover of Cuba, he begins making enemies of Cuba’s establishment — the doctors, lawyers, bankers, industrialists and politicians who support and profit from the large American corporations that operate in Cuba. These corporations are making huge profits in Cuba, thanks to that country’s laws that favor big business. Castro begins to rock the boat, and affluent Cubans don’t like it. There soon begins a massive out-migration of wealthy Cubans, some of whom want a return to the Cuba they enjoyed before Castro. Some of them begin plotting their own revolutions against Castro, and that involves guns and munitions. Enter Jack Ruby.

In February, 1959, while Castro is in Venezuela seeking a three-hundred-million-dollar loan, acting Cuban Prime Minister Jose Miro Cardona abolishes the National lottery, closes casinos and forces brothels out of business. As a result, thousands of Cubans lose their jobs. Castro, who had not approved the action, is furious. He forces Cardona to resign. Cardona leaves Cuba and goes to the U.S. to begin yet another crusade against Castro.

Changing Sides

More troublesome than Cardona is the Mafia’s reaction to the casino closings. Meyer Lansky, Lucky Luciano, Santo Trafficante, Jr., and other mobsters involved stand to lose millions, if not billions. They also start working on plans to get rid of Castro. They enlist the support of several anti-Castro groups. They know Ruby has been selling guns to Castro. They’re certain they can convince Ruby to sell guns to the groups opposing Castro. They were right.

Within months, Ruby is working with another gun runner who has C.I.A connections. His name is Tom Davis. They are selling guns to several anti-Castro groups, including the infamous Alpha-66. It didn’t take much to get Ruby to switch sides. As Don Browder would later say about Ruby, “During the pre-Castro years, the C.I.A. and Customs would not oppose gun shipments to Castro. After Castro turned communist, the C.I.A. and Customs encouraged shipments to anti-Castro forces. Ruby was in it for the money. It didn’t matter what side, just one that would pay him the most.”

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Within months after Castro’s victory, Ruby switches sides and starts running guns to the opposition with new partner, Tom Davis.

Tom Davis had gone to work for the C.I.A. in 1958 while he was serving a five-year probated sentence for bank robbery. He goes on the C.I.A. payroll in March, 1959, and in June, 1959, he begins working with anti-Castro forces at a secret base in Florida where he meets Jack Ruby. By now, Ruby is an accomplished gun runner who can supply just about any type of military grade weapon. He has been working for the C.I.A. since 1952.

For most of 1959, Ruby pops in and out of Dallas. In January, he’s living in an apartment on Hawthorne Street. His roommate, Johnny Meyers, becomes overly inquisitive about Ruby’s travels. Ruby moves out a few days later.

The F.B.I. also is curious about Ruby’s activities. Like the C.I.A., they know all about Ruby’s involvement as a gun smuggler. In March, 1959, the F.B.I. asks Ruby to become an informant. Ruby says he’ll do it. Special Agent Charles Flynn of the Dallas F.B.I. is Ruby’s contact. Ruby hopes that Flynn can use his influence to help keep the Dallas Police Vice Squad off his back. He can’t. On June 20, 1959, Ruby is arrested for dancehall violations at the Vegas Club. He is fined $25 and released.

A month before this minor incident, something occurred that would lead to one of the most mysterious periods of Ruby’s life. In May, 1959, Ruby’s old friend Lewis McWillie invites Ruby to come to Havana, Cuba, for a visit. McWillie had come to Cuba in June, 1958, before Castro came into power, to work as manager of the Tropicana Casino, owned by Meyer Lansky and Norman Rothman.

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In June, 1958, Lewis McWillie (L) comes to Havana to manage the Tropicana Casino, owned by mobster Meyer Lansky.

In May, 1959, the Tropicana is one of the few casinos still operating in Havana, and is on the verge of being shut down by Cuban authorities. Both Lansky and Rothman have been expelled from Cuba, and there is a lot of tension among employees of the casino. It seems odd that McWillie would invite Ruby to visit under those circumstances. Nonetheless, Ruby accepts, but it will be several months before he actually makes the trip.

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In May, 1959, the Tropicana is one of the few casinos still operating in Havana.

In August, McWillie contacts Ruby again. He wants Ruby to come to Havana, but not alone. He asks Ruby to bring Tony Zoppi, a gossip columnist for the Dallas Morning News. He wants Zoppi to do a story about Havana nightlife after Castro, hoping that a plug for Cuba might get the Tropicana back in the good graces of the Castro regime. McWillie sends Ruby two round-trip tickets to Havana. However, Zoppi turns down the offer, so Ruby goes to Cuba alone.

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Gossip columnist Tony Zoppi is invited to Havana by Lewis McWillie, but doesn’t accept.

There is conflicting information about the exact times, dates and points of departure and return for Ruby’s travel to Cuba in 1959. One tourist card from Cuban authorities shows that Ruby traveled from New Orleans to Havana on August 8, 1959, and departed Havana bound for Miami on September 11, 1959. A second tourist card from the Cubans indicates that Ruby returned to Havana from Miami the next day, September 12, 1959, and then after an overnight visit departed Havana for New Orleans on September 13, 1959.

However, Lewis McWillie disputes this information. McWillie claims that Ruby is in Cuba for only six days, and that he is with him the entire time. McWillie is still working at the Tropicana at the time, and Ruby is staying there, as well. At night, Ruby hangs around the casino where McWillie is working. During the day, the two spend all their time together, so McWillie claims he is sure of the length of Ruby’s stay and what he is doing during the entire six days. Of course Ruby could have told McWillie he was leaving after six days and then slipped away and remained in Cuba at another location. If this were the case, there would be no way for McWillie to know what Ruby was doing or for how long.

Further confusing this issue is Ruby’s safe deposit box account at Mercantile Bank in Dallas. Ruby’s bank safe deposit records show that he accessed his safe deposit box on August 21, 1959, and again on September 4, 1959. On both of those days, Ruby is in Cuba, if you believe official Cuban and American travel records. This indicates that Ruby probably is making undocumented trips to Cuba that neither the Americans nor Cubans know about.

The next question is, what exactly is the purpose of Ruby’s visit beyond the six days he spends with his friend, McWillie? It’s probably not to sell guns, because the market has dropped off considerably after the war ends. It’s either to do some sort of business with the American Mafia or with Fidel Castro. Ruby’s overnight trip to Miami on September 11, 1959, indicates some type of courier activity. In all probability, Ruby is carrying money back to the U.S. from Cuba. And it’s highly likely that he was carrying it for Santo Trafficante, Jr.

At the time of Ruby’s visit in August and September, 1959, Trafficante is being detained at what some call Triscornia Prison. However, Triscornia is not a prison. It is an immigration facility, more like Ellis Island than Alcatraz Island. And Trafficante is not really being detained. He is being housed in comfortable surroundings from which he is free to come and go at will. His “detention” is really a clever ruse concocted by Trafficante and Castro to fool Lansky and Rothman, both of whom were kicked out of Cuba, leaving millions of dollars behind. Trafficante convinces his good friend Castro to let him stay in Cuba as an advisor on operating gambling facilities. What Trafficante really wants to do is gather up the nearly two million dollars hidden in the Capri Hotel Casino and get it out of Cuba. This he does with the help of Jack Ruby on September 11, 1959, for which Ruby is paid $10,000 cash upon his return to Cuba on September 12, 1959.

All of this has been pre-arranged during a meeting between Ruby and Trafficante at Trescornia on August 16, 1959. Trafficante later denies such a meeting takes place, and goes so far as to deny even knowing who Jack Ruby is.

After Ruby returns to Cuba on September 12 to collect his $10,000 from Trafficante, he plans to hightail it out of Cuba and get back to running his clubs in Dallas. But before he can make his getaway, Fidel Castro intervenes. When Ruby arrives at the Havana airport for his flight back to New Orleans, he is arrested. Instead of being taken to jail, however, he is taken to the presidential suite of the Havana Hilton Hotel where Fidel Castro has set up his offices. When he steps off the elevator into the luxurious penthouse suite, he is greeted once again by the raspy voice of Celia Sanchez.

Celia greets him warmly with a smile and handshake. She is gracious, as always.

“Mr. Ruby…it is so nice to see you again. Thank you for all your kindness and assistance during our struggle. We are forever in your debt.”

Jack Ruby is flattered and impressed beyond description. He is so surprised and amazed by the reception, he can only stammer, “Thank you, thank you, thank you…”

Celia ushers him into Castro’s office. Fidel is not so gracious. He is seated at a large desk, puffing furiously on a cigar as he pores over numbers on a report. He doesn’t look up when Ruby walks in. Ruby is thrilled to see Castro and extends his hand warmly as he walks up to the desk. Expecting Castro to reciprocate, he is surprised when Castro looks at him and scowls through the cloud of cigar smoke that’s swirling around him.

“Fidel, sir…uh, comandante…congratulations on your victory,” says Ruby unsurely.

Fidel chomps down on his cigar and slowly stands up, glaring at Ruby the entire time,

“Why do you do it, Jack?” Castro asks as he starts to come around his desk. He reaches down and takes a Colt .45 out of his holster as he walks up to Ruby, who steps backward as Castro moves toward him.

“What’s wrong…what’d I do, huh, what’d I do?” Ruby stammers as Castro puts the gun to Ruby’s head.

Ruby screams and tries to step back, but Castro grabs Ruby’s necktie to stop him. Castro cocks the gun. Ruby grimaces and closes his eyes. He hears Castro pull the trigger, then the gun goes click. Ruby opens his eyes and Castro is standing there grinning. He lets go of Ruby’s tie, then turns to go back to his desk, chuckling to himself. Ruby’s legs go limp, and he staggers back against the wall.

“What the fuck, Fidel?”

“It’s a good thing for you that I forgot to load this thing,” Castro says with a chuckle as he waves his gun around.

Castro sits down at his desk, still looking at his gun. He motions Ruby to sit down, which he gladly does. Castro holds up the gun for Ruby to see.

“They gave me this gun in Texas,” Castro says proudly. Using the gun, he points at a Stetson hat on a rack in the corner. “And that hat…and this horse,” as he points at the picture of a horse on his desk.

“That’s a good looking horse…and hat,” Ruby says weakly.

Then Castro gets stern again. “I know you sold guns to Veciana,” says Castro as he opens his desk drawer and takes out a box of bullets and starts to slowly load his Colt .45. “My enemy,” Castro continues as he puts a second bullet in the chamber while glaring at Ruby.

Ruby starts to get nervous again and tries to talk himself out of the jam. “Your enemy? Veciana? He never told me that…I didn’t know that. Nobody ever told me! I wouldn’t have sold him guns if I knew that…”

“Bullshit,” says Castro as he slips the last bullet in the chamber and gives it a spin. He looks at the gun and then back at Ruby, who now thinks he’s a dead man.

Castro sighs, and slips the gun back into his holster.

“He never told you…and you never asked, si?” says Castro as he takes out a fresh cigar. Ruby shakes his head “no,” and says, “It never occurred to me. I thought you were friends.”

Castro lights his cigar and replies, “Friends today, enemies tomorrow…just like us, eh?”

“No, no, no…we’re friends…we’re amigos…forever!” Ruby replies as his voice gets a little louder.”

“I thought I could trust you, but I can’t. You care about only money.” Castro continues, as Ruby shakes his head “no.”

“No, no, you can trust me, I promise,” Ruby reassures Castro.

Castro ignores Ruby’s entreaties and takes a bank book out of his desk drawer. He tosses it across the desk to Ruby. “Here, this is yours.”

Ruby picks up the bank book and opens it. His eyes bug out and his jaw drops. It’s an account in the name of Jack L. Ruby. The balance is $1,000,000.

Ruby is dumbfounded. He doesn’t know what to say. He stammers, “This…this is mine…for me…for what?”

Castro shakes his head in the affirmative. “Yes, this is for you…all of it…one million dollars.”

“Well…what can I say…what’s it for?” Ruby replies.

“It’s for services…to be rendered,” replies Castro.

“Okay, sure, uh…what kind of services?” Ruby mumbles as he seems to be lost in thought.

“Spy services. The same thing you’re already doing against me…I want you to do for me. I want you to be my spy in the C.I.A., the F.B.I., the Mafia.”

“You’re paying me a million bucks to be your spy?”

“Si, one million U.S. dollars, just for telling me what others are doing and saying about me…or planning to do to me. That’s all.”

Ruby’s face lights up with a huge smile. “I’ll do it, damn right! We’ve got a deal, sir.” Ruby extends his hand. “Let’s shake on it.”

Castro reaches out to shake Ruby’s hand. “There’s just one catch.” Ruby’s face freezes as he replies cautiously. “What’s that?”

“You don’t get it for five years. This is a five year deal. You’ll notice there’s no bank name on the book, no account number. You’ll get that information five years from today…provided you faithfully do what I tell you to do. If you betray me, I’ll find out, and you won’t get your million dollars.”

Ruby thinks about it for a minute then asks, “Uh, what happens if, say, something bad happens. What if you die or get killed?”

“Then you get nothing. So it is in your best interest to keep me alive.”

Castro has incredible powers of persuasion. Ruby actually believes him. The guy who’s made a career out of hustling has just been hustled himself, big time. Fidel Castro now owns Jack Ruby.

The next day, Ruby flies from Havana to New Orleans. Before going on to Dallas, Ruby stops off at a bank in New Orleans where he has a secret safe deposit box in the name of one of his aliases. The box contains more than $50,000 in cash. He adds his million-dollar bank book to the stash, then heads for Dallas.