JFK's Grandfather: Patrick Joseph Kennedy

It was in this environment that Bridget Kennedy sought to support her family. She eventually landed a job at a stationery store. As the children grew older, she was able to buy the business and later expand it to include a grocery store. With the money earned from the store, P.J. was sent to Sacred Heart, a Catholic school. P.J. dropped out of school at age fourteen to work full-time as a stevedore.

Financial Success for P.J.

By the time P.J. reached adulthood, he was a large, confident man whose handlebar mustache and big blue eyes distinguished him from Boston's other Irish residents. P.J. followed in his mother's footsteps and took a chance on a business. He dipped into his savings and borrowed money from his mother to buy a floundering saloon in East Boston's Haymarket Square when he was twenty-two years old.

Although P.J. did not drink, many of Boston's Irish laborers did. With such a large clientele, P.J.'s saloon soon became a booming establishment, as he developed a rapport with customers. He was a trusted confidant who provided laborers with tidbits about job opportunities. As his capital grew, he acquired two more saloons and established a retail and wholesale liquor business.

Pursuing a Career in Politics

After his success in business, P.J. entered the political arena. At the time, politics was one of the only avenues of power for the Irish since the Brahmins guarded the world of business. In 1884, P.J.'s popularity among Boston's Irish helped secure his victory for a state-house seat where he served for five years.


“From his grandparents on his father's side, he inherited a certain self-possession and dignity of bearing which his father never achieved. Like P.J. Kennedy, John Kennedy commanded respect and attention from all who came in contact with him.”

— Doris Kearns Goodwin, The Fitzgeralds and the Kennedys: An American Saga

P.J.'s new success opened up his prospects with potential wives. Among his choices was Mary Augusta Hickey. She was the daughter of a Boston contractor who, like P.J., had achieved success despite the anti-Irish environment. Mary was more educated than P.J. since she had attended the Notre Dame Academy, a private Catholic school. Her social standing made her a good match for P.J., who sought to raise his own stature in the East Boston community. Shortly after their marriage in November 1887, Mary gave birth to Joseph Patrick Kennedy on September 6, 1888, and later to two daughters.

In the meantime, P.J. quickly learned that Massachusetts politics was a messy business. He managed to stay out of the limelight of corruption, but ballot stuffing, financial perks, and favors were all part of the business. After serving in the state house, P.J. won a seat in the state senate, where he served for six years.


The Brahmins did not give up their political clout willingly, but the Irish emerged as a strong political opposition in 1885, when Irish-born Hugh O'Brien was elected Boston's mayor. By 1914, the city's growing Irish population reached 39 percent. It became increasingly difficult for the Brahmins to win an election against an Irish candidate.

Enjoying a Powerful Position in Boston

By the time of his exit from the senate in 1895, P.J. had established himself as a powerful man in the community. From an office in his saloon he arranged job interviews, made recommendations, and once again, dabbled in politics. This time it was at the local level. He was appointed elections commissioner and fire commissioner, served in Boston's Democratic Party Board of Strategy, and secured a position as Boston's Ward Two boss. It was as ward boss that he wielded the most power. Along with other ward bosses for the North and South End and the Charlestown area, he had a hand in choosing candidates for state offices. Political clout also helped ensure P.J.'s financial success. He eventually acquired a coal company and held a notable amount of stock in the Columbia Trust Company, a Boston Irish — owned bank.

Serving alongside P.J. was John F. Fitzgerald, the North End Ward boss, a politician by nature, and a nuisance to P.J. He was everything that P.J. disliked. He was boisterous, flamboyant, he could bellow “Sweet Adeline” at a moment's notice, and his pride was insufferable. His physical stature was just as dissimilar to P.J. as his personality; he was a small man with dark brown hair. P.J. Kennedy, however, would eventually have to learn to tolerate Fitzgerald. Unbeknownst to P.J., their personal lives were destined to intersect.

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