For the most part, Joe Kennedy was insecure about Jack's political wherewithal. To balance the scale in Jack's favor, he set out to prepare the way for his son. He determined that Massachusetts was the best place for Jack to seek office, but it was still unclear what he would run for. Joe's first step was his acceptance of Massachusetts Governor Maurice Tobin's offer for a chairmanship over a planning commission assigned to survey the state's economy. In this position, Joe was able to rub elbows with powerful people in government and the media.

Developing Speaking Skills

In the meantime, Jack set out on his own campaign to gain visibility. Among the various public speaking opportunities was an American Legion meeting on September 10, 1945. The speech, which focused on postwar Europe, was a huge success. It was played on the radio and he received numerous requests for copies.

However, not all of Jack's speeches were as successful. Often, according to observers, he was wooden and serious, and he stuck closely to his prepared text. By all accounts, his public speaking ability was poor, especially when it came to extemporaneous speeches on local issues. Jack found that he was most comfortable when speaking about international politics.

As was often the case after a bad speech, Jack lamented his failure. Even so, his father was often by his side afterward to build him up. It was common for Jack and Joe to ruminate over the speech. They discussed all aspects of the address, from the delivery to the content. According to Jack, his father had confidence in his abilities and provided encouragement. Joe Kennedy used a combination of subtle criticism and positive reinforcement to direct Jack.

Jack's quiet style differed from the usual Boston politician. His grandfather John Fitzgerald was a prime example of the style of old Boston politics. His boisterousness and Irish charm had taken him a long way. Jack lacked this same type of charm and was noted for his aloofness. Often, instead of staying around to meet voters, Jack was one of the first to leave after a speech. His shyness was sometimes interpreted as snobbishness.

Candidacy Attacked

Initially, Joe desperately wanted Jack to run for lieutenant governor, but Joe listened to advice from his cousin Joe Kane. Kane pointed out that Jack's youth — he was only twenty-eight years old — would expose him to questions about his lack of experience in a run for lieutenant governor. On the other hand, a run for Congress in a democratic district would protect him from these types of questions. Kane also observed that as a Congressman Jack would be asked to give speeches and would remain in the public eye. In the position of lieutenant governor, Jack would essentially remain ignored.

In late April 1946, Jack and his father finally decided that he should seek election to the open congressional seat in the Eleventh District. In fact, Joe had already paved the way. James Michael Curley held the seat in the Eleventh District, but he had recently been convicted of fraud for his participation in mailing wartime government contracts. Joe Kennedy was able to convince him not to seek reelection by helping Curley pay off his debt with a generous donation of $40,000. Curley decided to run for mayor of Boston, and Joe Kennedy's contributions to that campaign set him back another $100,000.

Jack was happy with the choice. He still preferred national and international politics over local issues. Regardless of his preference, he soon learned that winning the election was going to take a lot of work. Joe Kane was wrong about one thing: as a congressional candidate, Jack still became the target of attack. He was running against nine other candidates in a district that included Boston, Charlestown, Somerville, and Cambridge, all of which were working-class areas. Jack had two things going against him. He was the son of a millionaire, and he had never lived in the Eleventh District except in his early childhood and college years.

His opponents could hardly forgive Jack for these failings. Even before he announced his candidacy, Dan O'Brien, an influential Cambridge undertaker, warned Jack he would lose, precisely because he was a carpetbagger. Other opponents pointed out that Jack was a rich kid who lived at a hotel, lacked political experience, and knew nothing about the needs of his potential constituents.

Even the newspaper the East Boston Leader had an opinion about Jack. In one column the newspaper declared: “Congress seat for sale — No experience necessary — Applicant must live in New York or Florida — Only millionaires need apply.” According to one columnist, Jack was a “rich kid,” had established a “phony” residence, and had done nothing that entitled him to win any votes. Jack was dismissed as an opportunist who sought to win based on his family connections.

Support from the Catholic Church

There was some truth to the press statements. Joe Kennedy had maintained close ties to Boston's Catholic church, especially Bishop Richard Cushing. Just as Joe knew how to work the political system, he was no stranger to getting exactly what he wanted from the church. Cushing hoped to be a cardinal one day, and he hoped Joe's contacts with the papacy might help him secure the position.

When Jack decided to run for Congress, Joe Kennedy knew he had Cushing's support. Over the years, financial donations to the church had paved the way for this type of sponsorship. In August 1946, the Catholic newspaper featured a photo of Jack and his mother handing a $600,000 check to Cushing for the construction of a hospital in Joe Jr.'s memory. Over the course of the congressional campaign, the Kennedys made more donations to various Catholic foundations that included St. Mary's Hospital, Christ Child Society, and the League of Catholic Women. Cushing invariably shared his favorable opinion about Jack when asked.