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How the Kennedy dynasty began in East Boston, with an Irish immigrant widow and her restless son

The roots of the family’s political and liquor fortunes start before Jack and even Joe, with Bridget Kennedy and her saloonkeeper son.

P.J. Kennedy and a partner bought a liquor store on Washington Street, at the edge of the North End.The Boston City Archives

Part 1: P.J. the Bartender

In mid-1879, The Boston Globe advertised the auction of Hayward’s saloon on Washington Street, a run-down South End joint with a sordid back story.

It had been an illegal groggery, the owner arrested a few years earlier. Another owner mismanaged the place and struggled to keep it afloat. Then came the night a 58-year-old man, drinking and playing pool with friends, went down to the cellar and put a gun in his mouth. His drinking buddies heard the shot and rushed to find “the lifeless body of their friend, who, a few minutes before, had been in the full enjoyment of life,” said the Globe. The owner decided to sell.

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Weeks later, a man named P.J. Kennedy, the restless son of Irish immigrants, paid the city $125 for a liquor license and bought Hayward’s for $3,000. His widowed mother, Bridget — with profits from her East Boston grocery store — had likely loaned her only son the funds that initiated his life as a liquor man. Except for some whiskey Bridget may have sold at her shop, Hayward’s would turn out to be the Kennedy family’s first real (and licensed) foray into the liquor business that would ultimately make their fortune.

On his first day behind the bar, P.J. made sure the front windows were open to the street, as required by an annoying new “screen law” that prohibited blinds, shutters, or curtains that might prevent beat cops from getting an easy view of his patrons. P.J. couldn’t even display bottles, casks, or barrels, per the constraints of the “foolish” and “cowardly” screen law, as the Globe called it.

P.J.’s start as a bartender and saloonkeeper coincided with a sharp shift in how Boston — politically, legislatively and culturally — viewed and treated the sale and consumption of alcohol, and the taxing and licensing of its buyers and sellers. The late 1870s into the 1880s saw Bostonians welcome the full return of saloon life after decades of limited or prohibited barrooms. Yet the fiery anti-alcohol forces of the day, and the remnants of Boston’s Puritanical past, meant there was no guarantee the days of happy tippling in America’s fifth-largest city would last. Smart saloonkeepers learned to diversify.

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More than 30 years after his parents fled famine and risked their lives to reach America, and more than 20 years past his father Patrick’s death by consumption, P.J.’s humble start in the liquor business would soon lead him toward politics and public service, and set his family on a remarkable ascent.


P.J. Kennedy in 1878, age 20, roughly a year before he bought his first saloon.From the John F. Kennedy Presidential Library and Museum, Boston

With Hayward’s up and running, P.J. turned his sights to a new business opportunity on East Boston’s Elbow Street, a short side lane named for its bent-arm shape. P.J. met with the landlord, a cabinet maker and prominent landowner named Treadwell, who gave him a tour of a ground-floor saloon located just doors away from P.J.’s old elementary school, the Lyman School. P.J. signed the lease, which would turn out to be one of the smartest, or luckiest, decisions of his life.

P.J.’s unnamed saloon — one friend called it simply P.J.’s “Elbow Street store” — sat just off Maverick Square, a few streets up from the waterfront and a stone’s throw from the herds of pedestrians commuting back from Boston proper by ferry and foot, ideally located for a quick nip on the way home. The narrow, angled street sat just outside the fray of downtown East Boston. With its unassuming entrance, the saloon was a dim-lit and quiet place for men (no women allowed) to shuffle across sawdust floors for nickel beers and peanuts after a long day on the docks.

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Such saloons played an increasingly important role in the lives of Boston’s immigrant Irish, a shared social space — not home or work or church — a place to learn about news from back home, to hold a party, a meeting, even a funeral. A place for a meal, to talk politics, to find a job. And sometimes, if the owner was willing, a place to sleep.

As a barkeep, P.J. was a generous and empathetic, willing to offer a free drink to someone with empty pockets, some food to a street kid hanging around outside, a few dollars to someone down on their luck. It was a practice he’d maintain the rest of his days. There on Elbow Street, a new kind of life began. Like his mother, he was an entrepreneur and a neighborhood fixture.

Towel over his arm, apron around his waist, P.J. pulled drafts behind the bar. He was about 5-foot-10; “well-muscled” and, from his days as a longshoreman and stevedore, “somewhat larger than the ordinary man.” Blue eyes and fair skin; dark reddish-black hair atop a “well-shaped head.” His most distinctive feature, adopted around this time and sported the rest of his days: a handlebar mustache that grew thicker as he aged, nearly exploding beneath his nose and curling at both ends.

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During lulls P.J. would don thin-framed glasses and bury his nose in a book or newspaper. He had a soothing voice but was more listener than talker. Rejecting stereotype, he was the rare Irish teetotaler, or at least a modest drinker and “rarely seen lifting a glass containing anything stronger than lemonade,” one family historian would claim. Another said P.J. had seen the dangers of drink as a longshoreman and “only on the most festive occasions” would allow himself a single glass of beer.

Just as his mother the widowed grocer attracted glowing compliments from patrons, P.J. the fatherless bartender seemed universally well-liked and trusted. He was a natural behind the bar, listening to stories and telling a few of his own, remembering names and asking about family members, soaking up and protecting neighborhood secrets.

P.J.’s future daughter-in-law, Rose Fitzgerald — her father John “Honey Fitz” Fitzgerald was also raised by a liquor-selling grocer — later said that her father-in-law’s spot behind the bar positioned him on the front lines of East Boston’s “news, gossip, celebrations, hopes and fears, troubles and tragedies.”

“He was a good listener, knew how to keep confidences, and had a compassionate spirit,” Rose said. “He helped people with loans, gifts, and advice. Often he passed the word onto somebody that so-and-so needed this or that, and P.J. Kennedy would appreciate it, asking nothing in return but goodwill. Everyone knew that he was an honorable man, and everyone respected him.”

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Whether it was coincidence or by design, P.J.’s Elbow Street shop happened to share an address with the Democratic Committee headquarters for East Boston’s Ward 2 district. There, P.J. Kennedy became a familiar and friendly face. And as Rose Kennedy would later put it, “Predictably, he became a political force in East Boston.”


Part 2: P.J. the Legislator

In 1882, having gained the notice of East Boston’s political elders, P.J. was elected to Boston’s Democratic Ward and City Committee, the start of his decades-long tenure as one of Boston’s most trusted and hardest-working Democratic leaders. He was 24.

He oversaw a crew of street-level lieutenants who registered voters, made sure Democrats in his precinct voted, while going door to door and checking names off his list. If a street had 50 voters, P.J. was expected to deliver 50 votes.

Bit by bit, his old life — fatherless stevedore, Irish bartender, grocer’s son — began to mesh with his upstart political life, as if he’d planned it that way.

P.J.’s progression from barman to statesman occurred at a transitional time for Boston politics, when the party of Lincoln dominated and the Protestant descendants of the city’s founders still held sway. In the immigrant wards — the lower half of East Boston, the North End, the South End, the West End — Irish voters favored the Democrats. But Democrats were the underdogs. Republicans held the majority on the Common Council and Board of Aldermen, and this dynamic — old vs. new, native vs. immigrant — was on full display in East Boston, where wealthy Republicans lived in big houses in tonier Ward 1 neighborhoods, literally looking down onto the tenements and saloons of mostly Irish Ward 2.

One lingering point of contention between the parties was P.J.’s business: booze. Republicans tended to favor Prohibition, and Prohibitionists were a powerful bunch. By the early 1880s, a new Prohibition Party had formed and regularly demonized men like P.J. for plying the immigrant classes with liquor, decrying the growing influence of saloons in politics. Yet men like P.J. had become “a social force in the community.” As The Nation had put it in 1875: “the liquor dealer is the immigrants’ guide, philosopher, and creditor. He sees them more frequently and familiarly than anybody else, and is more trusted by them than anybody else, and is the person through whom the news and meaning of what passes in the upper regions of city politics reaches them.”

In short, Irish saloonkeepers like P.J. were becoming a force in urban politics. As upcoming investigative journalist Lincoln Steffens would later riff, the fastest way to empty a city council chambers was to yell, “Your saloon’s on fire!”

The 1884 election of Hugh O’Brien as Boston’s first Irish-Catholic mayor opened the door a crack for other Irish candidates. And in 1885, P.J.’s political patrons decided their loyal, well-connected soldier was ready.

While most aspiring pols would run for Common Council or the more exclusive Board of Aldermen, P.J. Kennedy opted for neither. Displaying the same rebellious quality that once drove his mother crazy, he set his sights higher: on the State House on Beacon Hill, in the heart of Brahmin Boston.

At 27, he ran for the Massachusetts House of Representatives, and won.

He was the top vote-getter among East Boston’s candidates and, citywide, only a dozen of the 127 House candidates received more votes. He was headed to the historic red-brick State House, designed by Charles Bulfinch, who’d built the church where his parents had married, on land once owned by John Hancock, beneath a dome that had been sheathed in copper by Paul Revere.

He began his legislative career under a Republican governor (George D. Robinson), a Republican speaker of the House, and a Republican Senate president. He was one of 67 Democrats who’d serve in 1886 alongside 143 Republicans. P.J.’s victory placed him at the nexus of the slow-building success of his city’s Democratic machine, propelled by the influence of Irish and saloon politics.

The handlebar mustache that Kennedy wore for the rest of his life. from the John F. Kennedy Presidential Library and Museum, Boston

If the first election taught P.J. about the nuances of coalition building, the intricacies of caucuses, ward factions, dealmaking and horse trading, the next election — on his way to an unprecedented five straight terms in the House — would teach him about what was required to attain political longevity: friends, favors, trust and cash.

P.J. and a partner, J.J. Cotter, bought a liquor store at 12 Washington Street, at the southern edge of the North End near Haymarket Square, tucked beneath a carpet warehouse, beside a cigar and barber shop (15 cents a cut, 10 cents a shave). Above the door they installed a new sign, their names in 2-foot-tall letters in gold relief: COTTER & KENNEDY.

Months later, P.J. and another partner, J.J. Quigley, opened a liquor store and saloon on Border Street in East Boston, just a block from his mother’s grocery shop. Kennedy & Quigley would become a Border Street fixture for the next 20 years.

In 1887, as P.J. began his second term, with two profitable new ampersand-ed businesses to his name, he met his spouse-to-be, a woman who shared his history, his faith, his culture. A good Boston-born Irish Catholic woman, six weeks older than him, raised by immigrants who’d worked their way upward, from shanty Irish (father a laborer, mother a maid) to respectable. A proper woman who enjoyed music and theater, devotedly attended Mass — Catholic “bordering on the puritanical,” one chronicler would later say. He called her “Mame.” She called him Pat.

Mary Augusta Hickey was the eldest of six, three boys and three girls, born to James and Margaret, who went by Martha; they’d come from Cork a few years after the famine.

We don’t know how P.J. and Mary met, though one of Mary’s brothers once told her P.J. was “going to be a marvelous success.” Her father gave his blessing, his mother Bridget gave hers, and the couple married on November 23, 1887. On that cool Wednesday morning, the wedding became front-page news in the East Boston Argus-Advocate, which described pews filled with “friends and prominent people.”

Mary and P.J. welcomed their first child a year later. Instead of adding yet another Patrick to the Kennedy family tree, Mary decided to break the chain — “no little P.J.’s running around this house,” she insisted — and they settled on Joseph Patrick. She wanted her son to sound more American. Everyone called him Joe.

P.J. Kennedy’s children Joe, Margaret, and Loretta circa 1902.from the John F. Kennedy Presidential Library and Museum, Boston

Part 3: P.J. the Boss

After five years in the state Legislature, P.J. decided to step back and focus on his businesses.

P.J.’s mother had died in late 1888 — The Boston Globe called her “a woman of many noble and charitable traits” — and he’d lost his passion for the bedlam of front-line electioneering, the annual circus of caucus battles and campaigning, mobilizing voters, and late-night ballot sessions. That is, until the machine pulled him back in — and, before he knew it, he was up for a promotion. “I assure you that I shall strive to deserve your confidence,” he said, before being somewhat reluctantly elected to the state Senate in 1892. “My hope is that nothing I shall do can be construed as a betrayal of the trusts you have placed in my hands.”

Two years later, P.J. left the Senate with a reputation as a party loyalist, nonconfrontational, generous, patient and thoughtful. Colleagues called him “salt of the earth,” “a good man” and “a decent man.” He never hesitated to reach into his pocket for someone in need (though for anything more than a few dollars, he kept a ledger to track loans). Wrote one East Boston reporter: “He is genial and popular and, with a heart as large as an elk’s, is a friend to all.” And if someone asked how they might thank him in return, he’d reply, “Just say a prayer for my mother.”

But the life of a public servant could be exhausting. “We never sat down to dinner but what the doorbell would ring, and it would be someone down on their luck, coming to Papa for help,” P.J.’s daughter Margaret later said. Joe too would recall such incidents — his father’s empty chair at dinner, his mother’s wince and a plea to “tell them we’re eating” — though with a bit of disdain. “All I could see was their predatory stare,” Joe told a friend, remembering the “incessant demands” on his father. As Joe would later observe, after years of tagging along with P.J. to ward meetings and caucuses and fund-raisers, “Never was there a single moment when someone didn’t want something from him; never was there a single stretch of peaceful time when he could thoroughly relax and totally enjoy a good meal or a good book.”

Across seven years on the General Court, P.J. looked out for his constituents while also voting in his own self interest, ensuring that his post-legislative career would thrive.

P.J. emerged from the Senate with his liquor businesses intact, if under constant assault. Such threats had prompted him to start planning for a future that didn’t rely solely on liquor profits. Thus, a personal capstone to his legislative career was shepherding the passage of House Bill 420. After crossing the governor’s desk, the legislation gave a group of 16 men the authority to create a new bank they called the Columbia Trust Co., headquartered on Meridian Street in East Boston, about 50 yards from P.J.’s old saloon and the Ward 2 headquarters.

The bank would become integral to P.J.’s life, a source of income, loans, and prestige, along with headaches and investigations, a blessing and a curse. The bank would account for some of the highs and lows of his post-politics career — and, in time, of his son Joe’s career. Columbia Trust would be just one of many lucrative new private ventures, some of them controversial, all requiring a tiptoe around potential legal minefields.

Though some friends and benefactors had envisioned a different future for P.J. — viewing his days in the state Legislature as a step toward higher office — P.J. didn’t care to move to Washington to serve in Congress, or even across the harbor from East Boston to Boston to take a shot at mayor. P.J. harbored “no aspirations to leadership,” a colleague would later say. He seemed content to stay on his island, make some real money, playing the role of adviser to mayors, governors, congressmen, liquor men, and businessmen. Like politicians across time, P.J. the steadfast and quiet one would continue to capitalize on all he’d seen and heard at the State House, deftly navigating and manipulating a system he’d helped shape.

Nearing 40, in a master stroke of misdirection, P.J. the party loyalist ducked out of the limelight, stepped off the stage, and headed for safer waters: back to business, slyly building a modest, respectable empire.

There, he’d find far more political power than he’d ever held as an elected official.

P.J. photographed in the 1920s, a few years before his death. from the John F. Kennedy Presidential Library and Museum, Boston

In the waning years of the 19th century, P.J. hit an impressive stride, throwing himself into new ventures, both financial and social. Unconstrained by the limits placed on an elected official, he launched one moneymaking endeavor after another, investing in the same concerns that he’d voted for (or against), working with some of the same men he’d met (and helped) at the State House. As a family, they entered a new social stratum — undeniably high Irish and fully lace curtain. As P.J. got busier (and wealthier), they could even afford to hire domestic help, taking on a rotating staff of housemaids and cooks, including an Irish immigrant maid named (like his mother) Bridget Kennedy.

P.J.’s elevated status won him more invitations to exclusive clubs and, in turn, more business opportunities. An established member of the typical Irish organizations — the Ancient Order of Hibernians, the Knights of Columbus, the Elks — he was also asked to join the Redberry Club. Founded by vacationing “gentlemen” at Old Orchard Beach, Maine, the club was dominated by Boston’s Irish politicians, who fled their steamy city each August for weeks of song and drink, epic baseball games, fireworks, concerts, clambakes, and dances. Through his Redberry membership, P.J. became better acquainted with a former state Senate colleague, John F. Fitzgerald.

It was at Old Orchard Beach, wearing their matching Redberry swimsuits and singing their Redberry song, that the fates of P.J. Kennedy and “Honey Fitz” Fitzgerald became entwined. To the initial discomfort of both men.

With such similar backgrounds — immigrant parents from County Wexford, sons of a grocer and liquor seller, devout Catholics — they should have been friends, could have been soul mates. Like P.J., Fitzgerald had grown up poor, roving his Irish neighborhood barefoot and looking for trouble. “My playgrounds were the streets and wharves busy with ships from every port of the world,” Fitzgerald said. Like P.J., he’d discovered a path to success in politics — “the only field where I could get influence and opportunity.”

As two of the city’s top Democrats, working together was unavoidable. But they were in many ways opposites, Fitzgerald as voluble and extroverted as P.J. was reserved and introspective. “I suppose they must have grated on each other’s nerves at times,” Fitzgerald’s daughter, Rose, would write. “But they had many things in common: their immigrant background, the early deaths of their fathers, the personal determination, foresight, and hard work that raised them to their positions, and, of course, their sophisticated understanding of politics. I’m sure they understood each other and each in his way liked and admired the other.”

"The First Kennedys" is set to be released February 22.Handout

As Irish Catholic politicians, their primary bond was the fight against WASP-y forces still aligned against their kind. In 1895, during Fitzgerald’s first term in Congress, riots broke out in East Boston after the secretive anti-Catholic group the American Protective Association paraded through town on the Fourth of July, ranting about Irish Catholic “aliens” and “enemies of the state.” Rioters fired shots at a group of spectators on Border Street, hitting at least four men. A longshoreman named Wills, the father of seven, was shot in the back and killed. A Boston Globe artist’s rendering of the scene shows P.J.’s liquor store and saloon in the background, beneath a sign advertising lager beer sale. One of the shooters was arrested next door to Kennedy & Quigley.

Not one for speeches, P.J. asked Fitzgerald to visit and calm things down. At a fund-raiser for the murdered longshoreman, Honey Fitz addressed the “intense hatred of everything Irish and Roman Catholic” that still persisted, and he blamed radical, faux-patriotic men’s groups for trying to “monopolize all the Americanism in this country.”

“We are one people and owe the same duty to our country,” Fitzgerald told the crowd. “Why, then, this desire to set one class of people against another?”

Weeks later, the two men joined up at Old Orchard Beach, during the summer that would be remembered as the first time P.J.’s son and Fitzgerald’s daughter met. Joe was 7 and Rose was 5. A group photograph captured them sitting on the steps of a hotel.

As teenagers, Joe and Rose would fall in love, and Rose would credit their mutual attraction to those festive summers at Old Orchard, “a magical place.” The couple would marry in 1914, and eventually have nine children.

Even in his wildest dreams, P.J. the saloon man turned politician couldn’t have imagined that three of those grandchildren would reach the pinnacles of American political power. Or that in 1960, less than a century after this son of Irish refugees bought his first saloon, his grandson John F. Kennedy would become president.


FREE EVENT: On February 28, Thompson will read from “The First Kennedys” at the Massachusetts Historical Society. To learn more and to register for the event, which has in-person and virtual options, visit masshist.org/events.


Neal Thompson is a Seattle-based journalist and the author of five highly acclaimed books, including “A Curious Man,” “Driving with the Devil,” and the memoir “Kickflip Boys.” This story has been adapted from his forthcoming book, “THE FIRST KENNEDYS,” published by Mariner Books and set to be released on February 22. Copyright © 2022 by Neal Thompson. Reprinted courtesy of HarperCollinsPublishers. Send comments to magazine@globe.com.