The Sinatra Files (41 page)

    
Shortly before the 1960 election, the FBI learned that Giancana was involved in a plot against Castro—but not that the CIA was involved, according to a memo quoted in the Church committee report
.

    An October 18, 1960 memorandum from J. Edgar Hoover to Bissell, stated that “a source whose reliability has not been tested” reported that:

The plot against Castro might not have been Giancana’s only clandestine foray that fall. He suspected that his girlfriend was involved with an
other man, who ended up being bugged with the help of the CIA, according to the Church committee report. (Though the report didn’t identify them, it later became known that the girlfriend was the singer Phyllis McGuire and the target of the eavesdropping device was the comedian Dan Rowan, according to Curt Gentry’s Hoover biography.)

    After discovering the Las Vegas wiretap on October 31, 1960, the FBI commenced an investigation which quickly developed that Maheu and Giancana were involved in the case. In April 1961, Roselli’s involvement was discovered.

    
Meanwhile, the Castro plot continued, as detailed by the Church committee
.

    There is some evidence that Giancana or Roselli originated the idea of depositing a poison pill in Castro’s drink to give the “asset” a chance to escape. The Support Chief recalled Roselli’s request for something “nice and clean, without getting into any kind of out and out ambushing,” preferably a poison that would disappear without a trace. The Agency had first considered a “gangland-style killing” in which Castro would be gunned down. Giancana reportedly opposed the idea because it would be difficult to recruit someone for such a dangerous operation, and suggested instead the use of poison.

Edwards rejected the first batch of pills because they would not dissolve in water. A second batch, containing botulinum toxin, “did the job expected of them” when tested on monkeys. The Support Chief received the pills, probably in February 1961, with assurances that they were lethal, and then gave them to Roselli.

The record clearly establishes that the pills were given to a Cuban for delivery to the island some time prior to the Bay of Pigs invasion in mid-April 1961. Roselli reported to the Support Chief that the pills had been delivered to an official close to Castro who may have received kickbacks from the gambling interests. The official returned the pills after a few weeks, perhaps because he had lost his position in the Cuban Government, and thus access to Castro, before he
received the pills. Yet another attempt was made in April 1961, with the aid of a leading figure in the Cuban exile movement. He was paid advance money to cover his expenses, probably in the amount of $10,000. The money and pills were delivered at a meeting between Maheu, Roselli, Trafficante, and the Cuban at the Fontainebleau Hotel in Miami. As Roselli recalled, Maheu:

The attempt met with failure. Edwards believed the scheme failed because Castro stopped visiting the restaurant where the “asset” was employed.

    
Continuing its wiretap investigation of Giancana, the FBI contacted Maheu, the former agent. Acting on previous instructions, Maheu told the FBI that the bug had been placed as part of a CIA operation and referred the bureau to Edwards, the CIA security director. Hoover apprised Attorney General Robert Kennedy of the situation in a memo on May 22, 1961. The whole mess didn’t go over well with the FBI, according to the Church committee report
.

    Sam Papich, the FBI liaison with the CIA during this period, stated that the FBI was furious when it learned of the CIA’s use of Maheu, Roselli and Giancana because it might inhibit possible prosecutions against them in the wiretap case and in others.

Entries in the FBI files, however, indicate that the FBI vigorously pursued its investigation of the wiretap case. Then, on August 16, 1961, the Assistant United States Attorney in Las Vegas reported his reluctance to proceed with the case because of deficiencies in the
evidence and his concern that CIA’s alleged involvement might become known. The Department of Justice files indicate no activity between September 1961, when the FBI’s investigation was concluded, and January 1962, when the question of prosecution in the case was brought up for reconsideration.

    
It was in the following month, February 1962, that the FBI had discovered the evidence tying President Kennedy to Judith Campbell. The FBI later heard from Fred Otash—the private eye who had tried to set up Jack Kennedy in July 1960—that Campbell and the President were romantically involved. So now, Hoover had enough information to put it all together: Kennedy was sleeping with a friend of two alleged mobsters, Roselli and Giancana, who in turn were friends with the president’s buddy Sinatra and who were under investigation for illegal bugging. And Giancana—the same man who had helped the Kennedy campaign and therefore was angry with Sinatra for not getting Robert Kennedy and the FBI off his back—was secretly working with Roselli and the CIA against Castro
.

It was time to go see the president. The Church committee tried in vain to find out what happened at that meeting
.

    On March 22, 1962, Hoover had a private luncheon with President Kennedy. What actually transpired may never be known, as both participants are dead and the FBI files contain no records relating to it.

    
It’s clear, however, that President Kennedy was finally coming to grips with his own recklessness. Robert Kennedy, increasingly troubled by his brother’s public camaraderie with the mobster-friendly Sinatra, persuaded the president to distance himself from the singer. Sinatra reportedly flew into a rage when, after he spent considerable sums fixing up his Palm Springs estate to accommodate presidential visits, Kennedy canceled plans to stay there that March in favor of Bing Crosby’s place. President Kennedy also ended the affair with Campbell, who at some point became romantically involved with Giancana, too
.

For his part, Hoover decided to force the CIA’s hand on the question of
whether to prosecute the men under Giancana and Roselli who planted the illegal bug, as detailed by the Church committee
.

The day immediately following his luncheon with the President, at which Roselli and Giancana were presumably discussed, Hoover sent a memorandum to Edwards stating:

The CIA, of course, objected, and word was passed on to Robert Kennedy, the Church committee said
.

    In a memo dated April 24, 1962, Herbert J. Miller, Assistant Attorney General, Criminal Division, advised the Attorney General that the “national interest” would preclude any prosecutions based upon the tap. Following a briefing of the Attorney General by the CIA, a decision was made not to prosecute.

    
The briefing for Robert Kennedy occurred on May 22, 1962. In the Church committee report, one of the CIA officials recalled the attorney general’s reaction on being told that the CIA had conspired with the mob to kill Castro
.

    If you have seen Mr. Kennedy’s eyes get steely and his jaw set and his voice get low and precise, you get a definite feeling of
unhappiness…. [He said,] “I trust that if you ever try to do business with organized crime again—with gangsters—you will let the Attorney General know.”

    
Nevertheless, the Church committee discovered that the CIA plot against Castro continued. Another CIA official, William Harvey, had been put in charge of the project in late 1961
.

    Harvey, the Support Chief and Roselli met in New York on April 8-9, 1962. Four poison pills were given to the Support Chief on April 18, 1962. The pills were passed to Harvey, who arrived in Miami on April 21, and found Roselli already in touch with the same Cuban who had been involved in the pre-Bay of Pigs pill passage. He gave the pills to Roselli, explaining that “these would work anywhere and at any time with anything.” Roselli testified that he told Harvey that the Cubans intended to use the pills to assassinate Che Guevara as well as Fidel and Raul Castro. According to Roselli’s testimony, Harvey approved of the targets, stating “everything is all right, what they want to do.”

The Cuban requested arms and equipment as a
quid pro quo
for carrying out the assassination operation. Harvey procured explosives, detonators, rifles, handguns, radios, and boat radar costing about $5,000.

Roselli kept Harvey informed of the operation’s progress. Sometime in May 1962, he reported that the pills and guns had arrived in Cuba. On June 21, he told Harvey that the Cuban had dispatched a three-man team to Cuba.

Harvey met Roselli in Miami on September 7 and 11, 1962. The Cuban was reported to be preparing to send in another three-man team to penetrate Castro’s bodyguard. The second team never left for Cuba, claiming that “conditions” in Cuba were not right. Harvey terminated the operation in mid-February 1963. At a meeting with Roselli in Los Angeles, it was agreed that Roselli would taper off his communications with the Cubans. Roselli testified that he simply broke off contact with the Cubans. However, he never informed
them that the offer of $150,000 for Castro’s assassination had been withdrawn.

    
Sinatra, meanwhile, didn’t completely drop out of Camelot. Kennedy called his old friend while the star was hosting a mob wedding party in Atlantic City, according to a later summary of references in the Sinatra FBI files
.

    The following references … set out information pertaining to Frank Sinatra in connection with his appearance in Aug., 1962 at the 500 Club in Atlantic City with Dean Martin, reportedly as a special favor to Paul D’Amato, partner of Sinatra in the Cal-Neva Lodge at Lake Tahoe, Nev. D’Amato possibly had an interest in the 500 Club. Sinatra took over the first floor of the Claridge Hotel which guests invited to attend the wedding on Aug. 26 of the daughter of Angelo Bruno, head of the Italian mob in Philadelphia, could occupy. Information in connection with the hoodlum element was set out including contacts and associates of Sinatra. One contact was a personal telephone call which he received from President Kennedy on 8/23/62, the nature of which was not described.

    
Hoover wrote to his ostensible boss again that summer about the president’s call to Sinatra
.

    While conducting inquiry at the Claridge Hotel in Atlantic City, New Jersey, in connection with an investigation under our Criminal Intelligence Program, Agents of our Newark Office were confidentially advised by an official of this hotel that Frank Sinatra had received a personal telephone call from President John F. Kennedy on August 23, 1962. It is noted that Sinatra reserved a floor of this hotel during the latter part of the week of August 19-25,
1962, in connection with his appearance with Dean Martin at the 500 Club in Atlantic City.

    
His dreams of a favored seat at the court of Camelot dashed, Sinatra continued to associate with mobsters, though he may have been wearing out his welcome, as this snippet from a surreptitiously recorded September 13, 1962, conversation shows
.

    GIANCANA: That Frank, he wants more money, he wants this, he wants that, he want more girls, he wants … I don’t need that or him…. I broke my [expletive] when I was talking to him in New York.

    
Meanwhile, RFK’s Justice Department began to close in on Sinatra. An October 1962 FBI memo suggested that Sinatra had put his private plane, a car, and his home at Giancana’s disposal for assignations with his steady girlfriend, the singer Phyllis McGuire of the McGuire Sisters
.

FRANK SINATRA

The Los Angeles Division advised on October 2, 1962, that a physical surveillance reflected that a white Ford Falcon belonging to the Frank Sinatra Enterprises arrived at the Palm Springs Airport at 3:40 AM October 2, 1962, and contained one female and two males. FRANK SINATRA’s airplane bearing Number N71DE arrived at the Palm Springs Airport at 4:50 AM on October 2, 1962. PHYLLIS MC GUIRE at that time joined the individuals in the Ford Falcon described above. One of the individuals in the Falcon appeared to be SAM GIANCANA.

advised on September 22, 1962, that PHYLLIS MC GUIRE called telephone number 328-2105 in Palm Springs, California. At the time the call was placed, the informant advised that GIANCANA was present with MC GUIRE.