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  He needed a principal agent who was used to the ways of the covert world. He could not use an Agency employee because the risks for blowback were too great. And he could hardly trust a foreigner with this one. Rosselli was already on the books. In March 1961, well before Harvey was involved in Caribbean matters, Rosselli went to the Dominican Republic, accompanied by Howard Hunt of the CIA. Rafael Trujillo, the Republic’s dictator, was ambushed and killed on May 30, 1961, but the CIA was cleared of involvement in the assassination.

  Bill probably got in touch with one or more of his former colleagues at the Bureau, met them somewhere for a drink or two, and pumped them discreetly. The FBI man or men would have told Harvey, completely off the record, that Hoover had a tap on Giancana and that he was notoriously garrulous. They would have given Rosselli a good recommendation as an operator: his criminal record wasn’t all that egregious, and where Giancana spouted constantly, Johnny knew not to talk, except to the right people. What better solution to Harvey’s problem than a man who had lived his whole adult life as a member of a secret organization with very, very strict rules, enforced by the discipline of omerta?

  Another of Johnny’s advantages was that he was sincerely, almost touchingly, grateful to the country that had given him so much, even if the acquisitions had been illegal. And he needed brownie points in case his citizenship was questioned, which it subsequently was and, indeed, if the Feds got onto him for other malefactions.

  All these factors contributed to another sine qua non of clandestine operation: control. It looked as if Rosselli could be controlled by his case officer, Harvey. Still, Bill must have thought that the operation was sticky from the outset. He was sensitive to the potential for eruption; he was also cynically savvy to the ways of Washington and to the scavenger ethic of the media, even in those relatively innocent days. What if it became public that Jack Kennedy’s CIA had recruited elements of the Mafia to carry out an assassination contract on Castro?

  HARVEY TAKES OVER

  The actual transfer of Rosselli from the Office of Security to ZRRIFLE started out at the Savoy Plaza Hotel in New York on that April 1962 Sunday evening and then developed into a scene that, despite the IG’s official prose, is vaguely reminiscent of what would have happened if Jack Nicholson and Robin Williams had met the Marx brothers. Or it might have played better as a scene from Guys and Dolls.

  After discussions, Maheu suggested dinner at the Elk Room, a fashionable restaurant in a nearby hotel. O’Connell says that Maheu picked up the tab [i.e., Howard Hughes paid.]. They finished dinner about 9.30 or 10.00PM. Rosselli wanted to buy the group a nightcap, but since it was Sunday night, nearly all of the bars were closed. They walked around the neighborhood looking for an open bar and finally wound up at the Copacabana [a famous, celebrity-drenched nocturnal watering hole of the time, much frequented by gossip columnists and their stringers].

  They were refused admittance to the bar because of a rule restricting admission to couples, so they sat at a table where they could watch the floor show. Rosselli found himself facing a table at “ringside” at which Phyllis McGuire was sitting with Dorothy Kilgallen [one of the mainstream gossip columnists of the time] and Liberace for the opening night of singer Rosemary Clooney. To avoid Phyllis McGuire’s seeing him, Rosselli got his companions to change their seating arrangement so his back was turned to Miss McGuire.13

  EARLY CONTACTS

  Not surprisingly, Rosselli did not at first feel comfortable with Harvey. After the Copacabana caper, an overlap continued during which Jim O’Connell sat in on Harvey-Rosselli meetings in Washington on April 14, 1962. Thereafter O’Connell was assigned to Okinawa, and Harvey dealt with Rosselli alone.

  Joe Shimon, the former Metropolitan Police officer whose background remains obscure and whose presence on the periphery of the Castro operations is inexplicable, segued into Harvey’s circle, at least after Bill retired. Years later Shimon reminisced about the early 1960s and CIA Cuban operations to the investigative journalist and author Anthony Summers.

  The thing [the Castro assassination plot] wasn’t going too well. They sent a few teams and they never came back. Well, then Harvey was assigned to direct the show instead of Jim O’Connell, then he came [to Washington] and … Johnny was in a safe house for about six weeks with Harvey…. You see, Harvey … you got to give him credit … this was one of the greatest investigators in the world. He was very good. He had sources all over the world. He’s the guy dug the tunnel.14

  Joe Shimon, according to Summers, “loved to be a source.” His daughter, to whom Joe was something of a mystery, says that Mob figures, including Rosselli, often came to the Shimon family home in Arlington, Virginia, and that Harvey was a visitor from time to time.15 Joe also may have loved to embellish the truth, just a tad.

  After the last joint meeting with O’Connell, Harvey headed out of Washington by car on April 19. There is no record of how and when Rosselli went to Florida. According to Rappleye and Becker, Rosselli, another CIA officer, and perhaps later, Dave M. set up shop in the Kenilworth Hotel—not the Fontainebleau—in Miami and also “in a motel in an up-scale section of Key Biscayne.”

  Harvey told the CIA IG’s investigators that “he arrived in Miami on April 21, 1962, and found Rosselli already in touch with Tony Varona, the Cuban exile leader who had participated in Phase One [of the assassination operation]…. Harvey described the manner in which [some poison pills provided by the CIA’s Technical Services Division were] to be introduced into Castro’s food, involving an asset of Varona’s who had access to someone in a restaurant frequented by Castro. We [the IG officers] told Harvey that Edwards had described precisely the same plan…. Harvey replied that he took over a going operation—one that was already ‘in train.’ Edwards denies that this is so. O’Connell says that Harvey … is right.”16

  Shimon alleged that Harvey kept Johnny incommunicado for six weeks, probably in Florida, in the spring of 1962. Bill probably figured that Rosselli would present a handling problem, that he might be loath to accept discipline from a Fed. Harvey would have wanted to determine such vital factors as Rosselli’s motivation, his loyalty, and the extent to which he was under control of or in close touch with (a) Mafia figures and (b) any other intelligence or security service (including the FBI and the Immigration and Naturalization Service [INS]). To satisfy himself of Johnny’s bona fides, Bill probably conducted an interrogation himself or had it done by a trusted lieutenant, perhaps Dave M. It’s almost a given that Harvey had Johnny polygraphed.

  When Johnny emerged clean from the various preliminary inquiries, Bill or, more likely, the robust Dave M.—not trusting the usual trainers to meet the mafioso—gave Johnny a crash course in intelligence tradecraft, particularly the need for security and perhaps most especially the use of the telephone, countersurveillance, the use of cutouts, recruitment requirements, and name checking—the usually boring but vital aspects of intelligence work. Most probably, as circumstance permitted, the two men from worlds apart felt each other out, probed each others’ vulnerabilities and weaknesses—often over a bottle or two—and gradually formed the basis for an enduring palship.

  According to Ted Shackley, Harvey came to Florida periodically while Shackley was head of JMWAVE, primarily to see Johnny. Rappleye and Becker say that in Miami Johnny “frequented JMWAVE … sometimes attending the staff briefings, but more often engaging in demolition exercises with Ed Roderick, in rounds of cribbage, or heading off with Dave M. for drinking bouts.”17 Dave M. was assigned to Johnny’s raiders to exert day-to-day control over a group of buccaneers who could have turned a messy situation into a disastrous one. It’s more than possible that the U-Haul resupply caper recalled by Shackley in chapter 7 was actually a resupply mission for Johnny’s ops base in the Keys.

  Various accounts place Rosselli physically—sometimes in the uniform of a U.S. Army colonel—at the JMWAVE headquarters. Shackley, who was known by the Cubans as “El Rubio,” “the Blond One,” vigorously denies th
at Rosselli ever came close to JMWAVE.18

  Warren Frank and Star Murphy, who was in the JMWAVE office, have absolutely no recollection that Johnny ever appeared at the operation’s headquarters. Indeed, Star Murphy knew nothing at all of Johnny’s activities for the CIA until they became public in the 1970s.19 It is highly unlikely that Rosselli did, indeed, come onto the base. Such a visit would have been a severe violation of basic security and would have been anathema to Harvey.

  Whether Rosselli actually sauntered Miami’s boulevards in bird-colonel uniform, as has been alleged, is also subject to doubt. Johnny’s CIA contacts/controllers probably tried to keep Rosselli as entertained as possible at the raiders’ camp in the Keys. Recognition of such a well-known figure, especially in an American officer’s uniform, could have led to embarrassing repercussions.

  ROSSELLI’S SUBBASE IN THE FLORIDA KEYS

  The only description I have found of Rosselli’s paramilitary activities against Cuba comes from Richard Mahoney. Once Dick Helms personally cleared Rosselli for the assassination operation, the mafioso was covered as a colonel in the Army and Dave M. moved from the Langley basement to Florida. Toward the end of May 1962 the CIA built a small base for Rosselli’s unit on Point Mary, Key Largo, clearing out an acre or so of the thick mangrove forest for rough-hewn sheds and two crude structures. A floating dock was anchored on coral reef. The purpose of the base was to train snipers.20 Mahoney continues:

  Rosselli … was the only person who could make the incendiary [Dave] M. laugh. They would drink until the sun came up, usually joined by Rip Robertson, the hard-bitten Texan and decorated veteran of World War II who was the favorite “boom and bang” guy among the exiled Cubans [because he had actually participated in the Bay of Pigs landing operation]. A favorite bar was Les Deux Violins where, according to one of his Cuban operatives, “Johnny knew all the help by their first name, tipped hugely, and would tell farcical stories about his days with Al Capone.” Throughout his criminal life, Rosselli had befriended men more dangerous and sociopathic than these….

  … According to [a Cuban commander under Rosselli], Colonel Rosselli used the team from time to time for raids and other operations. Rosselli was one of only two Americans authorized to go into Cuba on clandestine missions.21

  Elsewhere in the accounts of JMWAVE’s activities in Florida is mention of considerable CIA activity in the Keys, where live firing exercises could be conducted without fear of compromise and fast boats could slip out to sea and return without question. These accounts may all be based on the same source, a colorful account attributed to Col. Bradley Ayers.

  Back in the mangrove, Rosselli wanted action. Recall that he had not served his country during World War II because the Feds had yanked him out of uniform to stand trial and then to serve his sentence for extortion. He had missed Korea. Now was his chance to prove his mettle, as well as his loyalty to Uncle Sam. Johnny’s yearning would have touched a responsive, perhaps even envious, chord in Harvey who, himself, had never served in uniform or fired a shot at any U.S. enemies.

  Rosselli and Dave M. separately kept Harvey informed of the operation’s progress. Sometime in May 1962, Johnny reported that the lethal pills and guns had arrived in Cuba. On June 21, only a month after Harvey took over, Johnny told Bill that a three-man team had been dispatched to Cuba. The IG’s report described the team’s mission as “vague.”

  There is no hard, documentary evidence to suggest that Rosselli ever put to sea or came close to Cuban shores on hostile missions, but there is at least this account of his derring-do, again according to Mahoney. Late in the summer of 1962,

  [Rosselli] Led his first nighttime mission across the Windward Passage in a pair of swift V-20s. The V-20 was the workhorse of the CIA fleet, admirably suited to its unique tasks. With its gun mounts and twin 100-horsepower Graymarine engines concealed by fishing nets, the boat looked like any other medium-sized craft plying the route…. The V-20’s top speed was 40 knots…. [A] Cuban patrol boat spotted Rosselli’s raiders and gave chase, ripping the bottom out of Rosselli’s boat with machine-gun fire. Rosselli jumped into the water and swam to the second craft, which managed to make it back to camp.

  On his second run toward the coast of Cuba, Rosselli’s V-20s were again intercepted and the lead boat was sunk. Rosselli managed to get aboard a small dinghy before the speedboat went under. He drifted alone for several days in the boat and was given up for dead back in Florida until an American patrol cutter rescued him and brought him back to camp.

  Giancana, for one, thought he was crazy to risk his life, but Rosselli had always been an over-the-top type.22

  Mahoney’s source was likely Bradley Ayers, who might have heard this story one night at Les Deux Violins—unless, of course, he participated in the op. I have seen no confirmation of these incidents, but they are in keeping with the Rosselli legend and thus may be a subsidiary part of Harvey’s story.

  If the story is true, Bill would certainly have conducted post-op debriefings when possible, to ascertain facts, perhaps to reprimand Johnny for recklessness, and then killed a bottle or two. Undoubtedly a few meetings during the summer of 1962 went uncatalogued—perhaps target practice in the Keys and drinking bouts—as the palship between the two deepened. Johnny was nearing sixty years of age and had given up a soft bed, but not booze, for a flamboyant existence dedicated to paying back a country that had given him the good (if illegal) life, and in so doing, acting at the behest of a man who had pursued him and his ilk for years. It’s not hard to imagine Harvey admiring Johnny for having put his life where his mouth was.

  There is, too, considerable irony that the CIA made an instant Army colonel out of an illegal immigrant who used a false name for most of his life, was a professional criminal, and was on unpaid leave of absence from the Mafia. The idea for the field-grade commission probably came from Johnny, who must have coveted the rank and the uniform as signs that he had, at last, made it in the world to which he so yearned to belong.

  The Church Committee report said that in late summer 1962 the CIA was preparing to send in another three-man team to penetrate Castro’s bodyguard. Harvey saw Rosselli in Miami on September 7 and 11, 1962, although no record indicates that Bill went to Johnny’s base in the Keys then. Johnny told Harvey that the lethal pills for Castro were ‘still safe’ in Cuba. “Harvey testified that by this time he had grave doubts … and told Rosselli that ‘there’s not much likelihood that this is going anyplace, or that it should be continued.’”

  The October missile crisis intervened, and in its midst, Harvey was officially removed from Task Force W. Bill’s handwritten marginal note on the committee report at that juncture says, “Actually, the termination [of the operation] started, then was expedited 11/62,” after Bill was removed from Cuban operations. The final, official termination of the CIA’s contact with Rosselli came in February 1963. But that was in no way the end of the relationship between Bill and Johnny.

  For all the reasons cited earlier, there is almost no paper on Johnny’s activities, or on the Johnny-Bill relationship. Harvey would not have written memoranda for the record to himself. His superior, Helms, did not want to know much about ZRRIFLE. And Scott D. Breckinridge and Kenneth E. Greer had to depend on interviews with CIA officers when they put together the IG’s report for Helms.

  The Church Committee report bends over backward to underline that Rosselli conducted all of his activities for CIA out of his own pocket, so no accounting records exist. “He paid his own way, he paid his own hotel fees, he paid his own travel…. He never took a nickel. He said, enigmatically, ‘No, as long as it is for the Government of the United States, this is the least I can do, because I owe it a lot.’ [Harvey’s note: ‘True!’] Edwards agreed that Rosselli was ‘never paid a cent,’ and Maheu testified that ‘Giancana was paid nothing at all, not even for expenses, and that Mr. Rosselli was given a pittance that did not even begin to cover his expenses.’”

  The committee, perhaps a bit prissily,
added, “It is clear, however, that the CIA did pay Rosselli’s hotel bill during his stay in Miami in October, 1960. The CIA’s involvement with Rosselli caused the Agency some difficulty during his subsequent prosecutions for fraudulent gambling activities and living in the country under an assumed name.” Harvey noted, “Inaccurate,” next to this item but provided no further comment.23

  Harvey spent the 1962 Christmas holiday, after Director of Central Intelligence John McCone had relieved him of command of Cuban operations and after the rapid termination of the Rosselli Cuba operation, in Florida. Bill saw Johnny “several times” while he was there. He gave Rosselli $2,700 to be passed on to the three “militia men.” Rosselli probably spent the holidays with his sister at Plantation Key, outside Fort Lauderdale; he and Harvey discussed the operation on the phone several times between January 11 and 15, 1963. They agreed that “nothing was happening. As far as Harvey knows, the three militia men never left for Cuba. He knows nothing of what may have happened to the three reported to have been sent to Cuba.”24

  Harvey was in Miami again February 11–14, 1963, well after he had been officially removed from Task Force W. He left a message for one of the Cubans that “it now looked as it if were all over.” With Helms’s approval that Rosselli be terminated as a CIA asset, Harvey flew in February or March 1963 to Los Angeles, where the pair “agreed that the operation would be closed off.” Rosselli would remain in loose contact with the principal agent, Varona. Thereafter, Harvey told the investigators, he had a couple of phone calls from Rosselli, who, because of the time difference, called Bill in the evenings at home.

  During another set of meetings in Florida in April, Harvey and Rosselli agreed on official termination and Johnny signed a quit claim. Bill and Johnny went out to sea in a chartered boat on two consecutive days, April 18 and 19, 1963, during which time they presumably discussed matters of mutual interest under circumstances that made surveillance of any kind almost impossible. During this period the pair had dinner with a third person, perhaps Johnny’s sister, Edith Daigle, or perhaps someone else. The dinner was official enough business for Bill to charge it, something he would not have done merely to recoup an out-of-pocket expense.