The Outfit

by Russo, Gus

  One night in 1926, while tuning the home piano of Capone (who had become like a father figure), young Kohlert was invited to stay for a spaghetti dinner. “We’re having a special guest,” Big Al informed the young man. At the dinner, Joe Kennedy showed up, and Kohlert watched as Capone and Kennedy struck a deal wherein Capone traded his whiskey (from his Canadian distillery) for a shipment of Kennedy’s Seagram’s brand. The exchanges were to be made in Lake Michigan, off Mackinac Island.

  Years later, when Kohlert was arrested in Britain (on stowaway charges - he had escaped Nazi Germany, but had no passport), he got a message out to the now ambassador to Great Britain, Joseph Kennedy. The note said: “I hope you remember me from that spaghetti dinner in Cicero . . . “ The next day, Kennedy came to the prison and saw to Kohlert’s release. In 1944, when Joe introduced Haig & Haig whiskey to Chicago, his agent was, according to FBI files, Tom Cassara, a Miami gangster who was shot dead soon after arranging the deal with an operative from the Outfit.

  Curly Humphreys also remembered Joe Kennedy from the Volstead era. Years later, Curly Humphreys’ daughter, Llewella, recalled her father speaking of his distrust of Kennedy, explaining that one of Curly’s hijacked booze trucks was hit by bombs tossed by Kennedy’s bootleggers, an apparent double cross by Kennedy, the details of which were not clarified for the family. Jeanne Humphreys also has vague memories of Curly speaking about a booze theft by Joe Kennedy’s forces. Kennedy’s interest in Al Capone’s liquor business was buttressed by Washington Post reporter and Joe Kennedy biographer Ronald Kessler, whose sources indicated that Joe promised a Chicago friend that “if he got Al Capone’s business, he would give him 25 percent. The man got the business, but Joe then fired him and hounded him so he could not find another job.”

  Curly Humphreys was also said by his family to have connected with Kennedy when the Irish patriarch moved in on the film business and eventually plundered the stocks of operations such as the Pathe newsreel company. Kennedy was a major player in Tinseltown in the 1920s when he purchased Film Booking Office (FBO) and Radio-Keith-Orpheum (RKO). While his family stayed on the East Coast, Joe lived in Beverly Hills for three and a half years producing seventy-six mostly forgettable films for FBO, and conducting a much publicized affair with actress Gloria Swanson. After his 1931 appointment by President Roosevelt to be the first chairman of the Securities and Exchange Commission, Kennedy intermittently returned to Hollywood, most notably to mediate a dispute in the boardrooms of Paramount Pictures, an uproar referred to as a corporate “civil war.” This was during the same period that the Outfit, through Johnny Rosselli, controlled most of the craft unions and received kickbacks, or extortion, from most of the major studios.

  Still other Outfit leaders crossed paths with Joe Kennedy. Johnny Rosselli told the Church Committee years later that he, like Curly Humphreys, remembered Joe Kennedy from his robber-baron, bootlegging, stock-plundering days. Rosselli testified that he knew Joe as far back as his 1930s Hollywood era, when the two used to golf and play cards together. According to Dade County (Florida) police files, Rosselli maintained his acquaintance with the elder Kennedy for the rest of Kennedy’s life, and that in a 1960 golfing chat, Papa Joe expressed his concern to Rosselli about his sons’ problems with women. Rosselli gave a similar recounting to D.C. police detective and mob expert Joe Shimon.

  Joe Takes Charge of the Backrooms

  Joe Kennedy had coveted the Oval Office for three decades, first for himself and then for his namesake son, Joe, Jr., who was killed in World War II. All those who met his second son, Jack, however, readily saw that he had the requisite charm, charisma, and intellect to succeed where the father had failed. It is now clear that Joe Kennedy concluded that for Jack to gain the Oval Office, the cooperation of all was necessary - and Joe meant all. As the patriarch himself said, “There are no accidents in politics.” He thus informed Jack, “I will work out the plans to elect you president.” Joe Kennedy biographer Richard Whalen summed up the ensuing electoral atmosphere: “Jack’s campaign had two separate and distinct sides. On display before the voters was the candidate, surrounded by clean-cut, youthful volunteer workers, the total effect being one of wholesome amateurism. At work on the hidden side of the campaign were the professional politicians whom Joe had quietly recruited. In his hotel suite and other private meeting places, they sat with their hats on and cigars aglow, a hard-eyed, cynical band, brainstorming strategy.’

  Early on, Joe set his sights on the massive labor vote. Likely unaware of the deal already cut between Nixon and Hoffa, Joe Kennedy attempted to forge a Kennedy alliance with the very man his son Robert was railing against in the McClellan hearings. The senior Kennedy called old family friend Frank Sinatra, asking him to first arrange a meeting with liberal Teamster leader Harold Gibbons. Gibbons met with Joe at the Kennedy compound in Palm Beach, whereupon Joe assured him that Bobby’s anti-Teamster vendetta had been put aside. ’Well, Mr. Gibbons,” Kennedy advised, “I don’t think there’s much of a war going on between the Kennedys and Hoffa. I hardly hear the name Hoffa in our house anymore.” Although the Hoffa-baiting Bobby was certainly not on the same page as Papa Joe regarding the Teamster overture, there is evidence that his more accomrnodating brother Jack was indeed. Jimmy Hoffa’s strong-arm Joe Franco was present when John Kennedy phoned Hoffa to offer a truce. Hoffa was entertaining the idea when Kennedy then had the temerity to ask Hoffa for a campaign contribution. According to Franco, this sent Hoffa into a screaming tirade against the brother of his nemesis, Bobby Kennedy. Joe Kennedy, however, would continue to assuage the fears of other Teamster leaders throughout the 1960 election year. He became fast friends with Gibbons, often sharing a table at Miami Beach’s Eden Roc Hotel, according to Gibbons’ secretary and PR director, Jake McCarthy.

  Even before the 1960 primary season commenced, Joe Kennedy began his plan to undo the damage caused by his firebrand son, Bobby. John L. Lewis, head of the United Mine Workers Union, related a story to the Chicago Tribune’s Walter Trohan. According to Lewis, Joe Kennedy flew in to see him soon after Jack’s announcement, asking for help in the important primary in West Virginia - a state overflowing with mine workers. Lewis told Kennedy to relax - he already had the state won. Lewis was well aware of the agents Joe Kennedy had dispensed throughout the state, dispersing cash to county assessors, judges, party chairmen, etc. The average payoff was said to be $4,000 to $5,000. It was understood that much of this was undertaken without Jack Kennedy’s knowledge. Lewis recalled, “His agents would say, ’Joe Kennedy is very interested in this state and he would like to help you out.’ He never mentioned Jack.”

  By the time Senator John Fitzgerald “Jack” Kennedy declared his candidacy for the 1960 presidential nomination, his father had determined that the electoral-rich state of Illinois had to be guaranteed. However, many experts feel that, given the strong Irish Catholic labor tradition in that city, support for Jack Kennedy was already a lock. Nonetheless, in his desire to acquire the state’s twenty-seven electors, Joe decided he couldn’t leave anything to chance, his own knowledge of the inner workings of that city having come from his long history as a businessman who had to keep Chicago’s local pols, unions, and hoods happy. As early as 1952, according to numerous accounts, Joe Kennedy had sent Kenny O’Donnell, a Harvard friend of Bobby Kennedy’s and an early member of the “Kennedy machine,” to Chicago to sow the seeds for young Jack’s eventual campaign for the presidency. O’Donnell would become the patriarch’s liaison to Chicago mayor Richard Daley. Joe Kennedy and Richard Daley were longtime political cronies, who lunched together often at Joe’s Merchandise Mart. So close was their relationship that Daley was seemingly cleared to spend Joe’s money as he saw fit. On one occasion, when candidate Kennedy was speaking in Chicago, Daley wanted the event televised nationally, at a cost of $125,000. The mayor instructed an aide: “Go over to Mr. [foe] Kennedy at the Merchandise Mart, and he’ll give you the check.” Which is exactly what happened.

  In truth
, Richard Daley had a selfish motive in getting out (or inventing) Chicago’s Democratic vote. Within the last year, Republican Ben Adamowski, the state’s attorney who was on the Republican slate, had announced major indictments against members of Daley’s infrastructure.9 Most disconcerting for Daley and the Outfit was the rumor that the recent charges would be the tip of the iceberg should Adamowski, who was personally protecting Morrison, win another four-year term. Among other looming problems was Adamowski’s investigation of Daley’s city commissioner of investigations, Irving “Sweep It Under the Rug” Cohen. According to Adamowski’s chief investigator, Paul Newey, “It was Cohen’s purpose to keep all the book joints going, but under wraps so that the media wouldn’t make an issue of it during an election year. Daley knew it was wide-open.”

  “Gee, the mayor is fit to be tied, Curly,” Pat Marcy informed Humphreys one day at Celano’s. “He’s letting the Polack, Adamowski, rib him, and he shouldn’t do that,” Humphreys replied. Humphreys then suggested that the “boys” should attempt to have a more friendly police commissioner installed to take the heat off of Daley. But all Humphreys’ local politicking was soon to be dwarfed by a new assignment emanating from Hyannis Port, Massachusetts.

  With the pundits predicting a virtual toss-up in the November election, the Kennedy patriarch had decided he needed the support of the Chicago Outfit, which was legendary for its ability to marshal foot soldiers to get out the vote locally and was known to be in control of many of the labor unions across the country. Papa Joe, knowing that Jimmy Hoffa would never endorse Bobby Kennedy’s brother, concluded that the key players would also have to include the non-Teamster labor unions so often infiltrated by the likes of Curly Humphreys. Kennedy intimates make it clear that Joe intended to embark on his own to run the election show, dealing with these less savory elements, hopefully in ways that would not become public knowledge. Those who knew Joe could hardly be surprised at just how low the Old Man would go to fulfill his dream. Jack’s aide-de-camp Kenny O’Donnell later acknowledged, “If Jack had known about some of the telephone calls his father made on his behalf to Tammany Hall-type bosses during the 1960 campaign, Jack’s hair would have turned white.” “You know, the old man is hurting you,” a friend warned Jack. To which Kennedy responded, “My father is working for his son. Do you want me to tell my father to stop working for his son?” Former Speaker of the U.S. House of Representatives from Massachusetts, and longtime Kennedy family friend, Thomas P. “Tip” O’Neill recalled, “These things happened, although Jack didn’t always know about them. But the Old Man made his own arrangements over and above the campaign staff. Jack certainly knew that his father was spending a lot of money.” A stock joke of Kennedy’s on the campaign trail had candidate Kennedy quipping, “I have just received a wire from my father. It says, ’Don’t buy one more vote than is necessary - I’ll be damned if I’ll pay for a landslide.’”

  Clearly, the candidate was not always aware of the details, but those very details, just now emerging, would later force the Kennedy family to play coy when the investigators into Jack’s murder, three years hence, were desperate for a motive.

  The decision reached, Joe began his secret liaisons with the Outfit, and many believe it was not a new occurrence. Joe Kennedy’s alleged dealings with Capone notwithstanding, the patriarch had surely reached accommodations with Chicago’s gangster element on other occasions. Chicago, after all, was the scene of one of Kennedy’s greatest financial triumphs, the purchase of the enormously undervalued Merchandise Mart for $12.5 million, of which he was rumored to have put up none of his own money. (It was reputed to be worth five times that much, and by 1969 it was valued at $75 million.10) With the Mart located in the heart of Chicago’s business district, it is virtually inconceivable that the Outfit-controlled unions did not have a vise grip on most if not all of the service and concession contracts that supported the behemoth. Joe Longmeyer, a veteran independent Chicago labor organizer, remembers one day when Curly Humphreys came into the furniture store where Longmeyer was working. “Humphreys arranged for the store owner to have entree at the Mart,” Longmeyer says. Such an opening allowed merchants to purchase wholesale goods in the Mart. “Since Humphreys had some kind of relationship with the management of the Mart, he got my boss in,” Longmeyer added. Few old-time Chicagoans doubt that Kennedy, either by choice or necessity, formed some sort of alliance with the Outfit to guarantee the Mart’s smooth running. As one of Giancana’s drivers recently remarked, “Nobody does real business in Chicago without knowing Mooney. Joe [Kennedy] knew where the power was.”

  Joe Kennedy’s first known election overture to Capone’s heirs was the luncheon at Felix Young’s, which Joe had had Johnny Rosselli arrange. However, when that summit produced no agreement, Joe Kennedy decided to approach the day-to-day boss, Mooney Giancana, separately. After all, they shared a mutual friendship with Frank Sinatra, whom Joe could use to press his case with Mooney.11 One other commonality practically defied belief: Mooney Giancana, Johnny Rosselli, and Joe’s candidate son all shared a girlfriend, Judy Campbell.

  Joe and Mooney

  In 1997, Meyer Lansky’s best friend and close associate, Vincent “Jimmy Blue Eyes” Alo, consented to a first-ever interview in which he recalled his knowledge of Joe Kennedy’s efforts to approach Mooney Giancana on behalf of his son:

  Joe came to me very early. Joe Kennedy and I had a mutual friend, Phil Regan, the actor and singer from Brooklyn. Joe sent Phil to see me.12 We met at the Sea View in Bal Harbour [Floridaj. Phil told me that they had it [the electoral vore] figured out to the last detail. Even that early they knew that Chicago would make all the difference. I don’t know how they knew it - this was before computers. The point is that they knew I knew Sam Giancana. Joe Kennedy wanted me talk to him about helping Jack in Chicago. I turned him down. I wasn’t in the habit of interfering in elections. The next thing I hear is that they went to Sinatra.13

  Although the Lansky faction, according to Jimmy Alo, had declined to serve as Joe’s liaison to the Outfit, Joe had far from given up. As Alo later heard through the mob grapevine, Joe Kennedy indeed called on Frank Sinatra, one of the best friends of Joe’s son-in-law actor Peter Lawford.

  When Lawford wed Jack Kennedy’s sister Patricia in 1954, he introduced the rakish Kennedy to the world of his fellow Rat Packers, which included Frank Sinatra, Dean Martin, Sammy Davis, Jr., Joey Bishop, and Lawford. Throughout the fifties, young Senator Kennedy trysted with his new pals in Hollywood and Las Vegas. Not long after his announcement to run, Jack Kennedy celebrated at the Sands in Las Vegas with Sinatra and the Rat Pack, who were there filming Ocean s Eleven. An FBI airtel memo from local agents to Director Hoover noted, “Showgirls from all over town were running in and out of the Senator’s suite.”

  Joe Kennedy knew that Sinatra had a special kinship with Mooney Giancana, an influence that might now be used to convince the Outfit to support the Kennedy master plan. Sinatra had been chummy with Mooney at least as far back as the early fifties, when Rosselli and the Outfit had given a push to the singer’s stalled movie career. The two exchanged pinkie rings, and Sinatra often closed his shows by singing “My Kind of Town (Chicago Is)” as a tribute to Mooney. Fellow crooner and friend Eddie Fisher remarked, “Frank wanted to be a hood. He once said, T’d rather be a don of the Mafia than president of the United States.’ I don’t think he was fooling.” However, in real mob circles, Sinatra was often derided as a “wanna-be.”

  In 1997, the author undertook new research for an ABC News film project that coincided with the release of the Seymour Hersh book The Dark Side of Camelot. One key task was to attempt to learn more about Joe Kennedy’s election appeal to the Outfit. What was learned added much detail to the long-rumored Sinatra contact. Although Frank Sinatra had previously refused all interview requests concerning his contacts with members of the underworld, that silence would be broken in 1997. After speaking with her father, Tina Sinatra was authorized to relay the following ac
count:

  A meeting was called [between Joe and Frank]. Dad was more than willing to go. It was a private meeting. I remember it was over lunch. I believe it was at Hyannis. Dad said he was ushered in. He hadn’t been to the house before. Over lunch Joe said, “I believe that you can help me in Virginia and Illinois with our friends. I can’t approach them, but you can.” Joe wanted Frank to approach the union leader with the most influence, which was Sam Giancana. Sam could rally his people - to make certain that neighborhoods were encouraged to get out and vote.

  It gave Dad pause. I know that it did that because he said that it did that. But it still wasn’t anything he felt he shouldn’t do. So off to Sam Giancana he went. Dad calls Sam Giancana to make a golf game and told Sam of his belief and support of Jack Kennedy. And I believe that Sam felt the same way.

  Apparently, Joe Kennedy decided that communicating with Mooney Giancana via Sinatra was unsatisfactory. Perhaps not trusting the crooner to make the case for Jack as strong as he could, Joe pressed to meet Mooney face-to-face. For years the talk of such a meeting has persisted in Chicago. Veteran Chicago Tribune Washington bureau chief Walter Trohan recently recalled what he had been hearing from ace police reporter (and two-time Pulitzer Prize winner) George Bliss: “He told me that in the course of seeking the presidency against Nixon, Joe Kennedy was dealing with Giancana. I couldn’t believe it at the time.” Former sports promoter and bookie Harry Hall, who knew Joe Kennedy, Mooney Giancana, and other luminaries, has a similar memory: “I spent a lot of time with the Kennedys in the Biltmore Hotel. Joe knew all the racketeers. I had heard he made a lot of promises to the Outfit for their support.” Recent interviews seem to, at long last, put some teeth into the reports Bliss and Hall were receiving.