So far as could later be established, Ruby’s interest in Cuba began six years before the assassination. According to James Beard, a former associate, he stored guns and ammunition at a house on Texas’s southern coast, prior to ferrying the weaponry into Cuba. Beard said he saw “many boxes of new guns, including automatic rifles and handguns” loaded aboard a military-surplus vessel, and that “each time the boat left with guns and ammunition, Jack Ruby was on it.” The shipments were destined for Fidel Castro’s revolutionaries, then still fighting to topple Batista. In the years before the revolution, Castro was supplied and supported from the United States, not least by the leaders of organized crime—currying favor against the possibility that Castro were to prove victorious.
According to Texas gunrunner Robert McKeown, whom the author interviewed, Ruby continued to ship in military supplies after Castro did seize power.3 By the spring of 1959, moreover, he was pursuing another project. He “wanted to talk about getting some people out of Cuba” on behalf of “a man in Las Vegas.” After the assassination, when it emerged that Ruby had been in Havana in 1959, he said he had merely taken an eight-day vacation in Cuba at the invitation of a man named McWillie.
Lewis McWillie, one of Ruby’s closest friends, had—in the words of a contemporary FBI report—“consolidated his syndicate connections through his associations in Havana, Cuba, with Santo Trafficante… .” He was in Cuba managing the Tropicana nightclub, in which Trafficante had a major interest. He had organized and paid for a weeklong trip to Havana for Ruby, McWillie was to say, in hopes that Ruby would get friends in the press to promote the club. Other information, however, suggests there was more than one visit—and activity that fit not at all with the story of a freeloading vacation in the Caribbean.4
Cuban immigration files were to show that Ruby arrived in Havana on August 8, 1959, flying in from New Orleans. Far from staying in Havana for just a few days, he was still there a full month later. Three witnesses, two attorneys and an architect, recalled having encountered Ruby at the Tropicana Casino in the first week of September, over Labor Day weekend. On September 8, Ruby mailed a postcard from Havana to a female friend in Dallas, mentioning in passing that “Mac”—presumably McWillie—“says hello.” An exit card showed that he flew out of Havana three days later. His travels, however, were not over.
Within twenty-four hours of leaving Havana, documents showed, Ruby entered Cuba again—this time from Miami—stayed for a night, then left for New Orleans. So Ruby made at least two trips, the first lasting more than a month, followed by a forty-eight hour shuttle that can hardly have been part of the pleasure trip Ruby and McWillie claimed. There were almost certainly other visits.
Elaine Mynier, a mutual friend of Ruby and McWillie who worked at the Dallas airport, said she “frequently” saw Ruby and McWillie coming and going. A Delta Airlines agent at New Orleans spoke of Ruby’s “numerous flights.” On August 10, two days after his first arrival in Havana, a police report had Ruby in Dallas being interviewed about traffic violations. Bank records for the following week placed him in Dallas accessing his safe-deposit box. On August 31, too, he was apparently in Dallas, and he was there again four days later. The Assassinations Committee would conclude that Ruby made at least three trips to Cuba, perhaps more, and “most likely was serving as a courier for gambling interests.”5
While in Cuba, information strongly suggests, Ruby met not only with Lewis McWillie, but also with Santo Trafficante. In the summer of 1959, as one of the most prominent targets of Castro’s gradual clampdown on Mafia gambling and narcotics operations, Trafficante was confined at the Trescornia detention camp on the outskirts of Havana. A former detainee named John Wilson, who was held in the camp at the same time, was to contact U.S. authorities in 1963 when news broke that Jack Ruby had killed alleged assassin Lee Oswald.6 At Trescornia, he reported, he had known “an American gangster called Santos [sic],” and that “Santos” had been “visited several times by an American gangster-type named Ruby” who “would come to prison with [a] person bringing food.”7
Years later, in an appearance before the Assassinations Committee, Trafficante would say carefully, “I never remember meeting Jack Ruby … I don’t remember him visiting me, either… . I never had no contact with him. I don’t see why he was going to come and visit me.” The Committee concluded that there was “considerable evidence” that Ruby did visit Trafficante at the camp. It linked him, too, to Trafficante associates in Dallas. One, an old Cuba hand named Russell Matthews, was described by one of his own attorneys as “probably the closest thing to the Mafia we’ve ever seen in Dallas.” There was also James Dolan, described as one of Dallas’ “most notorious hoodlums,” a man who committed acts of violence on Trafficante’s behalf, and who was also linked to the Marcello network in New Orleans. The telephone number of a Trafficante associate named Jack Todd was found in Ruby’s car after he shot Oswald.
Once they realized their day in Cuba was over, of course, crime bosses had begun backing the anti-Castro cause. Some, notably Trafficante, would agree to help CIA plans to murder Castro. Ruby, however, may at some stage not have played the Cuban game according to the Mob’s new rules. One of Ruby’s lawyers was to note that Ruby was fearful because “he had tried to arrange some sort of a deal with Cuba after Fidel Castro overthrew the Batista regime.” A psychiatrist who visited Ruby reported that there was, “considerable guilt about the fact that he sent guns to Cuba; he feels he helped the enemy and incriminated himself.” Ruby told the psychiatrist, “They got what they wanted on me.”. He did not say who “they” were.
Ruby’s first lawyer after he killed Oswald, Tom Howard, told the press that his client’s mind had simply gone blank at the moment of shooting Oswald. It was, the lawyer said, a case of “temporary insanity.” Insanity or conspiracy? Ruby’s behavior before the Oswald shooting provides some clues.
For a man judged by the Warren Commission to have “no significant link” with organized crime, 1963 caught Jack Ruby in a hail of coincidences. The Assassinations Committee, which used a computer to analyze the phone records of Ruby and other key individuals for the days and weeks before the assassination, found that men with the motive to kill the President had knowledge of Ruby’s “possible availability.”
In early October, just after the public announcement of the President’s forthcoming Dallas visit, a call went from Ruby’s telephone at his Carousel Club to a Louisiana number listed under the name of the ex-wife of Russell Matthews, the Trafficante associate from the Cuba days.
Late in October, Ruby called Irwin Weiner, a Chicago bondsman who headed the insurance company that underwrote the pension fund of Jimmy Hoffa’s Teamsters Union. He would later be charged with helping to defraud the Teamsters’ pension fund of $1.5 million—and found not guilty after the government’s chief witness had been shot dead by masked men. Weiner also knew Sam Giancana and Santo Trafficante. Two weeks before the assassination, Ruby had a conversation with Robert “Barney” Baker, whom Robert Kennedy had called Hoffa’s “roving ambassador of violence.” The next day, Ruby called another Hoffa lieutenant, Murray “Dusty” Miller, then phoned Baker again.8
Ruby, and some of those who had been in contact with him, would claim such calls had related to an effort by Ruby to solve problems he was having with the American Guild of Variety Artists, the entertainers’ union. Weiner, however, refused to discuss the nature of his Ruby call when questioned, and years later told a reporter their exchange had had nothing to do with labor troubles.9 Barney Baker, Hoffa’s henchman, claimed he and Ruby indeed discussed union problems. Why, though, would Jimmy Hoffa’s strong-arm man take time out to help with Ruby’s petty worries? The Ruby-Baker calls came at a time when Hoffa was under increasing attack from the Kennedy Justice Department. He had spoken of wanting both Kennedy brothers dead, as reported earlier, and he was close to Trafficante.
Assassinations Committee staff also probed a one-minute call Ruby made three
weeks before the assassination to a New Orleans number, CH 2-5431, which turned out to be the office number of Nofio Pecora, a lieutenant of Mafia boss Carlos Marcello. Marcello himself, a man who used the telephone only with extreme caution, had placed a call to CH 2-5431 in midsummer 1963.
Oswald’s uncle Charles Murret was an associate of Pecora. Oswald had been bailed, following the New Orleans street fracas over his Fair Play for Cuba Committee activity, thanks to the intervention of Emile Bruneau, another Pecora associate—eleven months after Marcello had reportedly talked of having the President murdered and “setting up a nut to take the blame.” Pecora “declined to respond” when asked by the Assassinations Committee about the Ruby call. He later said he “did not recall” speaking with Ruby, did not know him, and suggested he might have taken a message for somebody else on his property. The Committee was “dissatisfied” with these responses.10
Early investigators knew nothing about another factor the Committee uncovered. Jack Ruby was in dire financial straits in 1963, had borrowed more than a thousand dollars from the bank, was being pursued for rent arrears on his club premises, and the Internal Revenue Service was after him for nearly $21,000 in unpaid taxes—a figure that by midsummer rose to almost twice that figure. Yet suddenly, in the very last days before the assassination, Ruby began behaving as though he expected his finances to take a dramatic change for the better.
Ruby had long lived out of his hip pocket or left money littered around his apartment. On November 15, however, he began using a safe and discussed embedding it in concrete in his office. On November 19, three days before the assassination, Ruby told his tax lawyer that he had a “connection” who could supply him with money to settle his debts to the IRS. That day, according to Ruby’s bank record, there had been a mere $246 in his Carousel Club account. Three hours after the President’s assassination, however, Ruby would go to his bank carrying the then huge cash sum of $7,000—some $53,000 at today’s rates—in large bills stuffed in his pockets. He deposited none of the money, and about half of it had vanished by the time he was arrested two days later.11
The Assassinations Committee was to conclude that those with the motive to assassinate the President had in Jack Ruby “knowledge of a man who had exhibited a violent nature and who was in serious financial trouble.” Did the Mob take up its option?
The Weekend of the Killings
Shortly before 10 p.m. on November 21, Ruby went to dinner at the Egyptian Restaurant in Dallas with a longtime crony named Ralph Paul. The Egyptian was owned by one Joseph Campisi, whose description in official records ranged from being a “negative” member of organized crime to “suspected” and “definite.” Campisi knew associates of Santo Trafficante Jr. and had a long-standing relationship with Joseph Civello, who reportedly ran Dallas operations for Carlos Marcello. He would tell the FBI after the assassination that he knew nothing about Ruby’s background—yet later visit him in jail.
On the morning of the assassination Ruby dallied for hours in the offices of the Dallas Morning News. He ate breakfast there, and was noticed by a number of employees during the morning. He was in the advertising department—discussing publicity for his clubs—until 12:25 p.m., and he was there minutes after 12:30, when the shots rang out just blocks away in Dealey Plaza. His presence at the Morning News gave Ruby a viable alibi and more. Even before news that the President had been shot flashed through the newspaper’s offices, he was seated at a desk—a copy of the morning paper in hand—holding forth angrily about the now infamous black-bordered advertisement that “welcomed” President Kennedy to Dallas. When news of the shooting did come in, and people gathered round a television, Ruby appeared “obviously shaken … sat for a while with a dazed expression in his eyes.”
Dallas Morning News journalist Hugh Aynesworth, whose view was that Ruby had “feigned surprise” at news of the assassination, made a good point. Given that Ruby knew the President was in town, and given that the Dallas Morning News offices were a two-minute walk from Dealey Plaza, why had Ruby—if devoted to the President as he claimed—not bothered to go see him pass by?
Ruby soon began a telephone marathon. He called his club, saying he might decide to close up. He made a show of a call to his sister, handing the phone to a newspaper employee so that he could hear the sister cry out, “My God, what do they want?” As he left the newspaper building, Ruby would claim afterward, he was in tears. Twenty minutes later he was in the throng at Parkland Hospital, where reporters were awaiting news of the President’s condition. He tugged the sleeve of White House correspondent Seth Kantor, who had known him when he worked in Dallas, said what a terrible thing the shooting was, and asked whether he ought to close his clubs. Kantor said he thought he should and hurried on.12
Ruby did order the closure of his clubs, then launched into a spate of calls to relatives, friends, and businesspeople. One remembered him sounding very “broken up.” His sister recalled him saying, “I never felt so bad in my life, even when Ma or Pa died.” Was this a genuine reaction, or a show intended to build up the image of the Ruby, who would claim he shot Oswald on an impulse?
That evening, over a period of almost five hours, Ruby was seen repeatedly at the police station where Oswald was being held. At about 7:00 p.m., according to a reporter who knew him, he emerged from an elevator on the floor where Oswald was being questioned, walking between two journalists, hunched over and writing something on a piece of paper. Then he was seen hanging around outside the Homicide office where Oswald was being interrogated. According to the reporter, Ruby “walked up to the door of Captain Fritz’s office and put his hand on the knob and started to open it.” Officers on the door blocked his way at the last moment.
Ruby then left the police station, and showed up at a synagogue at a special service in memory of the President. The rabbi, who spoke with him, noted that he said nothing about the assassination. Then Ruby was off to the police station again, carrying a supply of corned-beef sandwiches for policemen he knew. He was still there after midnight when Oswald was led briefly into the mob of pushing, shouting reporters. Minutes later, when the District Attorney told the press that Oswald belonged to the Free Cuba Committee, Ruby piped up and corrected him. The D.A., he said, meant not Free Cuba—an anti-Castro group—but, as had by now been made public, the Fair Play for Cuba Committee, the pro-Castro group.
Ruby may have hoped to kill Oswald that first night at the police station. As he mingled with journalists and policemen, he was later to admit, he had his .38-caliber revolver with him.13 The hubbub at the station eventually eased off, but Ruby kept going. First he dropped into a nearby radio station. Then, in the wee hours, he spent an hour or so talking in a car with an off-duty policeman. This was Patrolman Harry Olsen, who had with him one of the women who worked in Ruby’s club. As they talked, the couple was to recall, Ruby cursed Oswald. He, for his part, would belatedly claim that Olsen told him “they should cut this guy [Oswald] inch by inch into ribbons.”14
Still not done, Ruby went to the other Dallas paper, the Times-Herald, and told more people how upset he was about the assassination. He went home at last at 4:30 a.m., but not to sleep. Ruby rousted his roommate, George Senator, and an employee out of bed and dragged them off by car on a bizarre dawn expedition. To the puzzlement of his companions, he had them photograph a large signboard that bore a poster attacking the Chief Justice of the United States. Senator and the employee could not make out whether Ruby thought the poster was the work of Communists, the John Birch Society, or a combination of both. Then at last, having added irrationality to the sustained show of grief, Ruby went home to bed.
The next day, Saturday, at noon, senior officers began to discuss when to move Oswald from the police station to the county jail. There was talk of doing it that afternoon. In two calls to a local newsman, Ruby asked for information on the move. At 4:00 p.m., the time first considered for the transfer, he was back at the police station aga
in. Police Chief Curry, however, advised the press to return next morning at 10:00 a.m.
That night, with the murder of Oswald less than twenty-four hours away, Ruby made more calls. At 10:44 p.m., a call went from Ruby’s sister’s apartment to Ralph Paul, the associate with whom he had dined two nights previously. One of his employees, who was to say she remembered Ruby having called, overheard Paul say something about a gun and exclaim, “Are you crazy?”15
Starting around 11:00 p.m., at his club, Ruby made multiple calls to Galveston, in the southeast of the state, trying to reach Breck Wall, a friend who was on his way there from Dallas. When he found Wall had yet to arrive, Ruby phoned Paul repeatedly at home until—at 11:44—he finally got through. The business that had been so pressing took only two minutes to conclude. Then, pausing just long enough to get the dial tone back again, Ruby made yet another brief call to Paul’s home number.
When FBI agents questioned him soon after Oswald’s murder, Paul did not mention these late-night calls. Later, he said Ruby had called merely to say other clubs in town were doing poor business. Wall, whom Ruby had striven so hard to reach long-distance, said the call had been merely about union business—the same explanation offered for Ruby’s conversations a week or so earlier with Hoffa’s aide Barney Baker.
On the morning of Sunday, November 24, Ruby and his roommate, George Senator, were to claim, Ruby stayed in his apartment till nearly 11:00 a.m.16 Other evidence suggested Ruby was out and about early that morning near the police station. Three television technicians said they saw him near their outside broadcast van. At 9:30 a.m., according to a church minister, Ruby and he traveled together in the station elevator—Ruby, he said, got out at the floor on which Oswald was being held.
Ruby was at home about an hour later, however, when one of his strippers called to ask for money. He sounded abrupt and pressed for time, but promised to wire her some cash. The money for the stripper is central to understanding the final events that led to Oswald’s murder. For Oswald, at that point, had just one hour to live.
Not in Your Lifetime: The Defining Book on the J.F.K. Assassination Page 37
