Town & Country: The Surprising True Story of How the Kennedy's Political Dynasty Began

[This excerpt appeared in Town & Country on Feb 22, 2022]

The Surprising True Story of How the Kennedy's Political Dynasty Began

The family has given us senators, ambassadors, and a president—but their rise started in a most unexpected way.

BY NEAL THOMPSON

In the early 1870s, a series of fires leveled swaths of East Boston and entire streets were rebuilt, breathing new life into the neighborhoods around Maverick Square, where Bridget Kennedy lived with her son and three daughters.

Making the most of this renewal, Bridget moved into an apartment in a rebuilt three-story home at 25 Border Street and moved her small grocery store into a new street-level space, sometime in 1875. After so many years of moving from place to place—at least a dozen relocations over the years—Bridget had finally settled in the place where she and her shop could stay put. Border Street would remain Bridget’s home for the rest of her days.

Her son P.J. and daughters Mary and Margaret lived with her above the shop, while daughter Joanna and her husband lived next door. As always, the memory of her dead husband Patrick was never far. Her new address was mere steps from their first apartment, just uphill from the docks where they’d arrived 25 years before, having fled the famine that decimated their homeland.

P.J. Kennedy, the grandfather of John F. Kennedy, got his start in local Boston politics in the 1880s—and began a family tradition that continues today.

When a chimney fire damaged the house next door, and the tenant moved out of 23 Border Street, Bridget rented that building too. Bridget now held the lease for the two adjacent properties, 23 and 25 Border Street; she began living at number 23, while her grocery/variety store/bakery occupied the ground floor at number 25. She sublet the upstairs apartments of both houses to her children and other boarders, mostly incoming Irish relatives and other immigrants.

The widowed shop owner was now, improbably, a business owner, a landlady, and, in time, the rare female property owner. She would eventually take out a $1,000 mortgage to buy 25 Border Street outright.

Thus grounded, her shop expanded and grew. By the late 1870s, family members helped with chores; young ones ran in the aisles and played in the back alley. When he wasn’t down on the docks working as a longshoreman and stevedore, 18-year-old P.J. would stop by to stock shelves and deliver parcels.

As a local businesswoman, Bridget came to be known as a “strong, cheerful woman . . . liked and respected,” with “a generous heart” and “a deep native shrewdness . . . a determined woman.” As in most Irish tenement neighborhoods, there was plenty of liquor being sold, too—two dollars for a gallon of port or sherry; California wine for 40 cents a quart; “Pure Rye Whiskey” for $2.50 a gallon. Bridget’s shop became a destination for local biddies, cooks, and seamstresses to gather and gossip—and sometimes tipple.

Her shop on Border Street would clearly have an influence on her son.

He never knew his father and didn’t have a brother. He was raised by the tough-minded women in his life, by sisters, aunts, nieces, and cousins who knew how to make a dollar, and by a strong and resourceful mother who introduced him to the business that would make him rich: slaking islanders’ thirst for liquor.

By his twentieth birthday, having discovered that he wasn’t cut out for the back-breaking life of a longshoreman or stevedore, P.J. tried his hand as a brass finisher at an East Boston machine shop. He soon decided factory life wasn’t for him, either. It was just a stop along the way. Not until he stood tall behind a brass-railed mahogany bar would he find his true calling.

His first foray in the liquor business was a shabby bar on south Washington Street called Haywards, which he bought in 1879 for $3,000, with a loan from Bridget. An agent from R.G. Dun & Co. said P.J. the saloonkeeper was “respectable” and “paid his bills so far as known,” but he was dubious about the saloon’s future—“chances for success are not considered very promising.”

Saloon life suited P.J., and he went looking for more investments. He bought a beer hall on Elbow Street in East Boston, then a longshoremen’s hangout near the East Boston docks. Later, he’d buy a saloon and liquor retail shop on Border Street, up the road from his mother’s grocery shop. Partnering with another first-generation immigrant’s son, he and J.J. Quigley opened Kennedy & Quigley, which would become a Border Street fixture for decades to come.

While many Bostonians still considered saloonkeeping less than honorable, P.J. had embarked on an enterprise with a seemingly limitless stream of customers, one that would provide income for his family for many years.

At some point, though, he sensed that spending every night behind a bar wasn’t quite his life’s work, either. He was ready for something more than serving suds to dockworkers. Maybe the business and social skills P.J. had developed could be used elsewhere? That’s what some of his more upscale patrons apparently suggested to the young man, who, as a trusted ear, had learned the ins and outs of East Boston, its whims and secrets, its inclinations and alliances. “He hears the best stories,” a years-long study of 1880s saloon life said of men like P.J. “He is the first to get information about the latest political deals.”

In the early 1880s, he effectively swapped his barman’s apron for a suit. Wisely, he chose to keep the Elbow Street saloon, which was conveniently located beside the Democratic Committee Headquarters for East Boston’s Ward 2. The saloon became P.J.’s own personal headquarters as he made a pivot from delivering drinks to delivering votes.

East Boston’s ward bosses kept hearing the name P.J. Kennedy, seeing it in newsprint for reasons other than the required public listing for a liquor license application.

There were the boat races in which P.J. led East Boston’s rowing crews to victory against other wards. There was the work he and his roommate, Nick Flynn, had been doing for the Excelsior Associates social club, assisting with concerts, literary talks and grand balls at Maverick Hall. At one such affair, P.J. served as assistant director and watched proudly as a hundred couples danced at “one of the most agreeable affairs of the season,” said the Boston Globe.

Some ward leaders got to know P.J. at his beer hall, where he’d still tend bar, talking politics as he poured them lagers. Or they saw him marching with other Democrats in the St. Patrick’s Day parades or working the streets and docks at election time, reminding people to vote—and for whom. Some had gotten to know P.J. at his mother’s shop, where she surely talked up her hardworking son.

These men opened their doors, welcomed P.J. in. They invited him to speak before local dignitaries at Lyceum Hall, where he stood nervously at the podium and “read some resolutions” before the evening’s activities, according to the Boston Transcript. He was not the most inspiring of public speakers, he and his mentors would learn. His skills shined brighter behind the scenes, as a community organizer and people manager.

These and other civic and political activities had a few things in common: they occurred within a block of P.J.’s saloons on Elbow Street and Border Street, they aimed to rebuild East Boston’s less-than-dominant Democratic Party, and they were tied, directly or spiritually, to the crusade for Irish independence.

Perhaps it was inevitable that P.J.’s entry into politics, his introduction to political audiences and newspaper reporters, would be linked to the injustices still grinding down on his parents’ homeland, Ireland.

After serving for years as a loyal Ward 2 soldier—as captain of his voting precinct for the Democratic Ward and City Committee; as chair of the Ward 2 caucus, charged with nominating Democratic candidates for Boston’s Common Council; as secretary of the Suffolk County Democratic Convention—P.J. the barman became P.J. the loyal Democrat. William Howard Taft would later highlight the political influence of men like P.J., advising other aspiring politicians to get to know “the proprietor of the social club of his neighborhood.”

Irish saloonkeepers like P.J. were becoming a major influence in urban politics. He and other brewers, distillers, retailers, and wholesalers parlayed their business success into politics, making steady inroads as council members or aldermen. A common thread woven through the published biographies of Boston lawmakers of the 1880s was “born in Ireland” and “engaged in the grocery and liquor business” or “engaged in the saloon business.” As investigative journalist Lincoln Steffens would later joke, the fastest way to empty a city council chamber was to yell, “Your saloon’s on fire!”

In 1884, when Grover Cleveland became the nation’s first Democratic president in 28 years, it boded well for Boston Democrats, who later that year put forth Hugh O’Brien, a wealthy newspaperman and former alderman, as candidate for mayor. O’Brien was elected as the first Irish-Catholic mayor of Boston, opening the door for other Irish candidates.

Suddenly, men young and old awoke to the idea that they didn’t necessarily need a Harvard education or a law degree to run for office. The Irish gift for gab turned out to be a powerful political asset. So did a saloon. By 1885, P.J.’s political patrons decided that their loyal, well-connected soldier was ready.

By now, the route was well-established: an aspiring pol would get involved with his local ward, make a name for himself, and run for the Common Council. In rare cases, he might aim for the more exclusive Board of Aldermen. P.J. opted for neither. Instead of starting local, he looked past his island wards and set his sights on the statehouse on Beacon Hill, the historic home to the Massachusetts General Court that he’d visited as a schoolboy, in the heart of Brahmin Boston.

He was just 27 but decided to run for the Massachusetts house of representatives. Did he discuss the idea with Bridget? Did she encourage him to take a chance, just as she had? Did she leverage her community connections? Did he get the okay from the ward leaders he’d served well in recent years? Probably all of these. In mid-1885 he began his run for the office of state representative.

P.J. was an earnest and hardworking candidate, good with names and eager to help “our kind”: Ward 2’s Irish Catholics. He met with constituents and talked about his support for the labor movement. He favored the new East Boston soup kitchens, which fed the persistent flow of hungry incoming immigrants.

Bridget no doubt played a role in spreading the word that her once rascally son was running for office, gushing about the upcoming election at her shop and after Sunday mass. It had been 20 years since she’d opened her first store. She knew her customers well, and they knew and trusted her. If she suggested to longtime neighborhood shoppers that they consider P.J. Kennedy for the statehouse, her customers (especially the Irish ones) surely listened.

On November 3, 1885, turnout was heavy in Ward 2. Voters crowded the streets and alleys around polling places, most of them within a block of P.J.’s saloon, which was packed with P.J.’s precinct lieutenants and other ward soldiers. Polls closed at 8 p.m. and ballots trickled in until 10. As the count began—with P.J.’s friend Nick Flynn, as ward secretary, tallying votes—one ward leader began taking bets, placing hundreds of dollars on P.J. for the win.

At 11:15, the results were announced: Kennedy had defeated the Republican and Prohibition slates to become the new state representative for Ward 2. He’d done it—leapfrogged over all the men his age (and older) with similar political aspirations. Sadly lost to history is his mother’s no-doubt proud reaction. Also lost: whether P.J. celebrated by allowing himself one beer.

On January 6, 1886, a week before his 28th birthday, P.J. was sworn in as a member of the 107th Massachusetts General Court. At his orientation session he received a copy of the fat Manual for the Use of the General Court. He was assigned to the House Printing Committee. He met the longtime house doorkeeper Captain Tucker (a well-known temperance activist) and was assigned his seat, number 85, near the back of the cavernous house chamber, which thirty years earlier had been full of Know Nothing legislators.

As one of 67 Democrats who’d serve alongside 143 Republicans, he began his legislative career under a Republican governor, a Republican speaker of the house, and a Republican senate president.

P.J.’s hard-fought victory placed him at the nexus of his city’s Democratic engine, which was slowly gaining steam, propelled by urban and saloon politics.

A year later, P.J. was reelected—“Genial and popular,” said the East Boston Argus-Advocate, he won his 1886 election “by an extremely large and flattering vote”—on his way to five straight terms as state representative.

The baby of the Kennedy family was now 29. He’d started to make real money: $650 a year from his legislative salary alone (roughly $18,000 in 2020 dollars), plus expenses, on top of steady profits from liquor sales. He met at 81 Border Street each Monday night with brewery salesmen and liquor importers and made rounds to his businesses. (P.J.’s beer supplier, James T. Fitzgerald, lived above the Border Street saloon; his older brother John F. Fitzgerald was at the time considering his own run for elected office, in the North End.)

In 1887, as P.J. began his second term, he found himself surrounded by in-laws, aunts, cousins, nieces and nephews, the unmarried patriarch of the Kennedy clan. He still lived on Border Street, less than 500 feet from his birthplace, in an apartment above his mother’s shop. His saloon farther up on Border Street, plus his duties representing the neighborhood where he was born and raised, kept him anchored to his family and community.

It’s that East Boston community that soon introduced him to the daughter of another Irish immigrant couple, a good Boston-born Irish woman, six weeks older than him, who would become his wife.

Among their peers, P.J. Kennedy and Mary Augusta Hickey were far from alone in deciding to marry on the verge of thirty. P.J.’s political contemporary (and sometime rival) Martin Lomasney would not marry at all—“never had a romance, never attended a wedding,” he’d crow—and another upcoming Irish politician, James Curley, would roar that he had “no time for girl friends.”

Men like P.J. and Lomasney were hyperfocused on the game: the caucus meetings amid cigar smoke, the rattle of beer glasses during strategy sessions at the ward office, the obsession with votes, votes, votes.

Sensing that the first move would need to be hers, Mary Hickey chose and pursued P.J. Kennedy—not the other way around, as she would later boast. She’d watched him walk the streets of East Boston, sometimes right past her window, on his way to and from his liquor shops, the ward office, and the ferry, bound for the statehouse downtown. He seemed so determined and self-assured, and Mary decided one day to “set her cap” for the young mustachioed legislator.

They married on a brisk Wednesday, November 23, 1887. The wedding was front-page news in the East Boston Argus-Advocate, which described pews filled with “friends and prominent people,” dozens of dignitaries, city councilmen, clerks, the postmaster, Democratic committee leaders and legislators. Everyone gathered afterward at the Hickeys’ house for a reception, where P.J. gave his bride a pair of diamond earrings to celebrate their union.

That afternoon, P.J. and Mary boarded a train for New York, the start of a honeymoon that would take them to Washington, D.C., where P.J. met with Democratic leaders to discuss party affairs. A honeymoon to the nation’s capital was typical of P.J.’s focus on politics, and his like-minded bride would not have been surprised by a tour of the US capital instead of a romantic beach resort.

In time Mary would become a true partner—in P.J.’s work, his politics, and his liquor businesses. She’d lay out his clothes each morning and in the evening make him eat a bowl of chowder before going to meetings, so he didn’t come home hungry and grouchy. A granddaughter would later call Mary “very firm and very severe,” and another dubbed her “the power behind the throne.”

Though their union was never described as passionate or especially loving, the newlyweds shared a common goal, the goal of all immigrants’ kids: a better life than their parents’, and a child that lived past infancy.

Ten months later, on September 6, Mary and P.J. welcomed their first child.

"At some point, P.J. sensed that spending every night behind a bar wasn’t quite his life’s work."

At Most Holy Redeemer church, in the sanctuary where P.J. had been christened, the newest Kennedy was baptized. Friends, relatives, and P.J.’s business associates and ward comrades visited the Kennedys’ apartment to bestow congratulations, deliver flowers, and catch a peek at the baby dressed in a lacy oversized christening gown. Instead of naming him Patrick of P.J., Mary chose a less Irish and more American-sounding name. A boy named Joseph, she believed, was less likely to rile up anti-Irish sentiments.

P.J. was reelected that fall, as voters sent him back to the statehouse for a fourth term. “The contest was the most exciting for many years,” said the Boston Globe, calling it “a Waterloo for the Democratic Association.”

Weeks later, on a stormy December night, friends threw a party for Mary and P.J. to celebrate their first anniversary, the arrival of their first child, and P.J.’s victory. They showered the couple with toasts and gifts, including a large reclining chair for P.J. Late into the night, friends sang and gave bawdy speeches. The place was filled with state senators, city aldermen, and police officers.

Bridget wasn’t able to make it to her son’s party, though. She’d been feeling unwell, tired and struggling to walk, spending more time in bed. (Some accounts claim she was suffering from arteriosclerosis and heart trouble and was confined to her apartment above the store.) On December 18, a week before Christmas, she suffered a stroke. It’s unknown whether she was taken to a hospital or spent her final days at home. The end came quickly. Bridget Murphy Kennedy died on December 20, surrounded by her weeping family. She was 67.

A wake was held at her home, the place busy with Bridget’s grandkids and her sisters, her nieces, nephews, and neighbors. Services followed at Most Holy Redeemer. The snow had melted and the temperature reached sixty degrees. In the church, Bridget’s casket was mounded by floral wreaths and bouquets. A large crowd gathered, a chorus sang hymns, and Father Lawrence McCarthy, who’d recently baptized P.J. and Mary’s boy, praised Bridget as a good mother and a devout Catholic who was loyal to the East Boston community.

Bridget was laid to rest at Holy Cross Cemetery, five miles north in the town of Malden, a resting place developed twenty years earlier for Boston’s Irish Catholics. Days later, the East Boston Argus-Advocate praised her as “a well-known and charitable lady” while the Boston Globe called her “a woman of many noble and charitable traits and her loss will be deeply felt by the community.”

Did she have cut-glass tumblers or a crystal water pitcher? Lace curtains in her windows at Border Street? A parlor room for guests? These benchmarks of success were among the lofty hopes of the immigrant Irish, but Bridget left no evidence as to whether she’d achieved the dreams of so many Famine survivors. She’d at least lived to see her son’s success, or the start of it. His name was now preceded by an honorific: the Honorable P.J. Kennedy.

She managed to leave behind something for her kids, an actual estate, the likes of which might have seemed unimaginable when she first stepped off the coffin ship forty years earlier. After P.J. met with his lawyers to settled Bridget’s affairs, his mother’s business—the store fixtures and furniture, the mortgage for 25 Border Street—were tallied up and valued at $2,200 (about $60,000 in 2020 dollars). She wasn’t rich. But she didn’t die poor.

Within a week of her funeral, an ad appeared in the Boston Globe that read like a coda to the life of the former maid, Bridget Murphy Kennedy. Perhaps posted by one of Bridget’s daughters, it read: “Wanted: strong girl, plain general housework; also small girl to take care baby. 25 Border St., East Boston.”

The shop would stay open for another year, though it’s unclear who ran it during that time. Seven months after Bridget’s death, a squad of East Boston police officers raided 25 Border Street and arrested a couple, Winifred Preston and Thomas Daly, charging them with violating city liquor laws and seizing “a large quantity of malt liquors.” Then P.J. liquidated the place.

Adapted from THE FIRST KENNEDYS by Neal Thompson, published by Mariner Books. Copyright © 2022 by Neal Thompson. Reprinted courtesy of HarperCollinsPublishers.