Joseph Kennedy, the wealthy financier and Wall Street jackal, had been a partner of Diamond Joe Esposito during the days of Prohibition; together the two men had made a fortune smuggling sugar and mash into the East Coast and trans-continentally. Momo was never partial to the toothsome fellow, disliking the smiling hypocritical facade of the Irish Catholic businessman hiding a thieving pirate. "If there ever was a crook it was Joe Kennedy," he told his brother and confidante, Chuck. "Old man Kennedy made over a million bucks selling the market short before it fell. He manipulated the whole damn Depression."

Kennedy's son Jack was the shining star senator from Massachusetts who, many said, was eyeing the White House and who, because of his daddy’s bucks and influence would inevitably reach his goal. In the early 50s, Momo had pulled strings for the old man to have his son's career-threatening-marriage to a lower-class girl annulled and all legal documents eradicated.

Joe Kennedy now had come to Chicago for another favour to ask, and when he strolled into the East Ambassador Hotel that evening in mid-1955, under cover of disguise, he bore a desperate frown. He needed to get out of a scrape. Frank Costello, the New York boss, had put a contract on his life for refusing to perform a number of owed favours for the Syndicate. Kennedy explained to Momo that he had meant no insult, but that he was just maintaining a distance from Costello should the Kennedy name be re-linked to the rackets and ruin his son's career. "You know how it is," he told Momo, shrugging apologetically.

Giancana made him squirm a little until, panicky, Kennedy blurted out what Momo wanted to hear. "If my son is elected President he'll be your man. My son, the President of the United States, will owe you his father's life. He won't refuse you, ever. You have my word." Within the week, Momo talked to Costello. With the promise that they would have their own man in the White House, the mob called off the hit on Joe Kennedy.

When in January, 1957, 31-year-old Bobby Kennedy helped form the McClellan Committee to investigate mob activity, Momo thought it was just for show, as Joe Kennedy wouldn't dare let his sons seriously threaten the mob -- not after the recent bail-out. But, then the committee started making headlines by dragging the Outfit boys in front of television cameras for questioning, Momo was anxious.

Bobby, who served as chief counsel to the Senate Select Committee on Improper Activities in the Labor or Management Field, seemed to be playing his part to the hilt. He arranged to have the spun-off McClellan Committee's proceedings air live so that the American public could hear for the first time what the phrase "organized crime" was all about. Over the next several months, top mobsters -- Momo among them -- were served subpoenas to appear before the committee. And throughout the process, Joe Kennedy kept insisting that this was all a masquerade. In fact, he announced, Jack was going to throw his hat into the 1960 Democratic Party Race and, since he was considered the front runner, would then require Momo to drum up the unions to cast him their hefty votes for Presidency.

Momo agreed, but inwardly remained skeptical. His appearance before the McClellan Committee on live TV did not soften his apprehension. Charade or not, Chief Counsel Bobby seemed to take genuinely sadistic pleasure in ridiculing Momo on a million American TV screens. Despite it, Momo maintained his cool and answered every insinuation with the words he recited from habit: "I refuse to answer on the grounds it may incriminate me."

Momo worked overtime to prepare a defense against possible Kennedy treachery. Jack was known within underground circles as a lecherous womanizer, so it didn't take long, with the help of mob whoremasters and local police on Momo's payroll, to collect incriminating evidence. As he confessed to his brother, "I got enough evidence to ruin two political careers. I've got pictures, tape recordings, film, you name it. The American public would be real happy to see their President being serviced by three women!"

Celebrities like Frank Sinatra and others whose careers were Outfit-dealt also were used as tools to frame the Democrat's white knight nominee. They introduced Jack to a glittering array of ambitious women for whom he would quiver like an alley cat in heat. One was Marilyn Monroe, the seductive-voiced curvaceous bombshell; another was Sinatra's former girlfriend, social climber Judith Campbell. Momo himself bedded both these women and from them learned Jack's most intimate secrets.

The Presidential Campaign now in full swing, Momo decided to measure the Kennedys' loyalty to him before he contributed further support. He had had his union men in the field for months promoting Jack and had yet to spot a visible benchmark of their appreciation. A barometer was necessary. He asked Joe Kennedy to yank his son Bobby from that ridiculous witch-hunting committee. Surprisingly, Joe obliged. Bobby resigned without a whimper and turned his full-time attention to managing Jack's campaign. Momo was encouraged.

John F. Kennedy, after a series of television debates versus challenger Richard Nixon -- the most historical political face-offs since Lincoln argued Douglas -- became the 35th President of the United States on November 8, 1960. It had been a scrappy fight, for in the end he beat Nixon by only one-tenth of a percent, so close that the Republicans demanded a recount. The obvious was undeniable: Without the Outfit's forced union votes (which came in strongly for Kennedy) as well as the strong Illinois vote (which Momo begifted, thanks to threats of broken necks and often double- and triple-voting techniques) the race would never have been won.

During the election, the Kennedy campaign had pinpointed certain areas of the country that could go either way in the election, and they need help securing these areas. The word was passed from Kennedy’s father, the powerful and ambitious patriarch of the Kennedy clan,Joseph Kennedy, to Sinatra: Ask your “friend” in Chicago to help us with West Virginia and Cook County, Illinois. This deal with Giancana would guarantee that he would arrange to rig the presidential election in Illinois and ensure that his son John would become president.

Judith Exner, girl friend of Giancana, acted as a courier, shipping satchels of money between the Chicago boss and John Kennedy which was used to help Kennedy the underdog defeat Hubert Humphrey, who was the favourite.

Giancana was willing to oblige, delivering his home turf as well as West Virginia where his outfit had enough sway to influence the election. The Mob had agreed to help, but obviously expected something in return. When Kennedy won, Giancana expected the new administration to show its thanks by getting the feds off his back. He expected that the new president would lay off key mob figures and that investigations into organized crime, focusing on these figures would be put to rest.

Named the new Attorney General, Bobby resumed his attacks on the mobs, more vehemently than ever. It all became clear to Momo; he told his Outfit, "The Kennedys are still out to erase all obligation to us" as, Bobby Kennedy's commission handed to the press their list of the top 30 mobsters in America. The name Sam Giancana headed the list. Without giving time for this incident to cool, Bobby ordered FBI surveillance on Momo. He spotted the agents everywhere - behind him at the bank, they were around him at the ballpark, they trailed him when he drove his car. And when he traveled and partied with his new girl friend, Patty McGuire, of the singing McGuire Sisters, they were there, too, at the airports, the restaurants, the hotels.

The usually tight-lipped Momo who never revealed what he thought -- about anything -- lost his calm one afternoon. In front of a crowd at a busy airport, he approached one of the bloodhounds and, with a threatening finger in the man's chest, shouted, "Screw your boss Hoover and his boss, Kennedy! I have the lowdown on all the damn Kennedys and one day I'll tell everything. Then the whole world will know what hypocritical bastards they really are!"