This book is a sweeping and revealing insider look at court history and the life of William Brennan, champion of free speech and public access to information, and widely considered the most influential Supreme Court justice of the twentieth century.

Before his death, Brennan granted coauthor Stephen Wermiel access to a trove of personal and court materials that will not be available to the public until 2017. Wermiel also conducted more than 60 hours of interviews with Brennan over the course of six years. No other biographer has enjoyed this kind of access to a Supreme Court justice or to his papers.

Justice Brennan makes public for the first time the contents of what Jeffrey Toobin calls “a coveted set of documents,” Brennan’s case histories, in which he recorded the strategizing behind all the major battles of the past half century, including Roe v. Wade, affirmative action, the death penalty, obscenity law, and the constitutional right to privacy.

Revelations on a more intimate scale include how Brennan refused to hire female clerks even as he wrote groundbreaking women’s rights decisions; his complex stance as a justice and a Catholic; and new details on Brennan’s unprecedented working relationship with Chief Justice Earl Warren. This riveting information—intensely valuable to readers of all political persuasions—will cement Brennan’s reputation as epic playmaker of the Court’s most liberal era.

"This sweeping biography of one of the most influential justices ever to serve on the Supreme Court of the United States invites the reader to witness the details of William J. Brennan Jr.'s personal life, the darker moments, as well as those that shine. It seats the reader in Brennan's chambers to listen to his conversations and see the memoranda exchanged with other justices and his law clerks ... In sum, the biography is an intimate account of Brennan's life, especially his 34 years on the Court."--Newark Star Ledger

"The book offers an intelligent and interesting account both of Brennan's decades on the Court and of the broader developments in American life that intertwined with the Court's work."--Ed Whelan, National Review Online

"The book takes care to place decisions and opinions in the context of Brennan's personal history, judicial philosophy and larger societal factors. It's deliciously gossipy when discussing how certain justices voted and what their opinions were of each other, but that information's also vital when understanding how the court operated."--Dan Herman, Pacific Northwest Inlander

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BILL'S SON

Newark, New Jersey, seemed cloaked in mourning on May 16, 1930. The sudden death two days earlier of City Commissioner William Joseph Brennan Sr. had eclipsed even the economic disaster enveloping the city in the early months of the Great Depression.
 Thirty-eight years had passed since Bill Brennan arrived by steamship in the United States at the age of twenty, just another poor, anonymous Irish immigrant. An estimated forty thousand citizens—equivalent to 9 percent of the city's entire population—lined up through the night for a chance to enter the rotunda of City Hall, where his body lay in state. Standing vigil nearby was an honor guard of labor, police, and firemen Bill had led as head of the stationary firemen's union and during four terms as city commissioner. The next morning, six police horsemen and a marching band led off the parade of two thousand political, business, and union leaders accompanying the hearse. Three New Jersey National Guard airplanes dipped low overhead, dropping flowers on the mile-long funeral cortege. Throngs of somber onlookers lining Broad Street lifted their hats as the hearse passed by on its way to St. Patrick's Cathedral.
 Seated in a carriage behind the hearse was William J. Brennan Jr. The younger Brennan, twenty-four, had rushed home by propeller plane from Massachusetts, where he was finishing his second year at Harvard Law School, when it had become clear that his father would not survive a sudden bout of pneumonia. But he had arrived too late to say goodbye to the man who, for decades to come, would dominate his view of the world and the course of his career.
 In life, Bill, who stood nearly six feet tall, had overshadowed his still boyish-looking namesake, five feet eight, in every way. Brennan's classmates at Barringer High School teased in their yearbook that the commissioner's son got by thanks to “Dad's reputation” and predicted his ambition was “to follow dad.” Brennan had dutifully taken his father's advice and enrolled at the University of Pennsylvania's Wharton School and then Harvard Law, an Ivy League pedigree that far outshone the six grades of school Bill had completed. Brennan, soon to begin his first summer job as a lawyer, probably could not have imagined as he looked out on the massive funeral procession the extent to which he would exceed his father's professional achievements as well. Bill, however, had always expected nothing less from his oldest son.

William J. Brennan Sr. had bloomed late, his first quarter century in Ireland and America filled with far more failures than successes. Born on December 26, 1872, in Roscommon, a poor rural county on the border between central and western Ireland, about fifty miles north of Galway, Bill was the oldest of six children of Patrick Brennan, an illiterate tenant farmer from the tiny village of Cloonshanville, and Elizabeth Kelley, of Leggatinty, an equally small nearby town. Patrick Brennan had “married into” the Kelley farm, moving there and eventually taking over the tenancy. Bill's grandparents likely made do with a couple of cows, sheep and pigs, and some hens, just enough for them to survive the Irish potato famine that devastated Ireland a quarter century before his birth. Bill's parents, born just after the famine, stuck it out in Ireland even as millions of others fled.
 Life for Bill, as for his ancestors before him, did not extend much beyond the nearest town of Frenchpark, where farmers gathered on Friday market days to sell animals and produce and to exchange gossip. Bill, who attended primary school intermittently when he was not helping his father on the farm, decided he wanted out. At the age of sixteen he traveled to England to work as an apprentice in an uncle's pottery business at Longton, Staffordshire, near Newcastle. Bill lasted only three years in the position before concluding that neither England nor his uncle's business was for him. In 1892 he set out for the United States. Family lore has it that he landed first in Boston, although Bill ultimately chose Trenton, New Jersey, as his destination.
 Trenton, capital of the nation's pottery industry, was a natural choice, given his apprenticeship in the trade. But Bill's timing could not have been worse. The Panic of 1893 soon plunged the nation into a deep depression. Trouble in the pottery industry had started even earlier. Orders dried up, and factories-including the Maddock plant where Bill worked-shut down. With little education and no skills other than in pottery, Bill next followed the path traveled by earlier waves of Irish immigrants in New Jersey: manual labor. He found a job as a laborer on a gravel train on the Philadelphia and Reading Railroad and quickly worked his way up to brakeman on the Lehigh Valley Railroad, although he soon lost that job too, during a strike in 1893. The victim of economic depression, free trade, and a broken strike in just his first months in America, Bill's loyalties would forever lay with the workingman.

Leaving Trenton in the summer of 1894, Bill headed to Newark, a brawny industrial boomtown fifty miles to the north. Although the city was overshadowed by New York, its more cosmopolitan neighbor just a few miles to the east, Newark's civic boosters exaggerated only slightly when they claimed its factories built every product sold in the United States. Downtown, smokestacks dominated the skyline above factories producing everything from beer and chemicals to patent leather and hoisting engines. Webs of telegraph wire and trolley cables ran above its cobblestone streets.
 Newark seemed a place of limitless possibilities to immigrants like Bill, who boosted the city's population by a third, to 246,070, during the 1890s. With its population and industry growing rapidly together, however, Newark was also a place of considerable squalor. Nowhere did opportunity and poverty entwine more than in the industrial section of town along the Passaic River known as Down Neck, or the Ironbound, a reference to the railroad lines surrounding the neighborhood. Succeeding waves of new arrivals crowded into dilapidated houses adjacent to the neighborhood's many factories.
 By the time Bill arrived in Newark, the children of the Irish immigrants who had first come to the city in large numbers during the famine era had begun to ascend toward middle-class respectability. Bill had to start at the bottom, right alongside the new immigrants from southern and eastern Europe. He laid tracks for the B. M. Shanley Company, then converting streetcars from horse to electric power, and shoveled coal at a licorice factory, a job that made him detest the taste or even the smell of licorice thereafter.
 Then, around the dawn of the new century, Bill finally found steady employment at the forty-acre riverfront P. Ballantine & Sons brewery. As a stationary fireman, Bill worked inside the brewery's power plant, where enormous coal-fed boilers belched out the steam powering all the chutes and slides, fermenting vats, and mashers from which poured barrel after barrel of lager. Watching the boiler pressure gauges and repairing them when they broke put Bill in the middle of the boiler-room hierarchy, above the coal shovelers yet below the operating engineers who supervised the power plant. Coal dust filled the air. Temperatures rose well above 100 degrees in the summer. Still, Bill surely preferred the smell of beer to licorice. He enjoyed the camaraderie among the mostly Irish stationary firemen and may have had one of his coworkers to thank for introducing him to his wife.
 Family accounts differ about how Bill, handsome, with wavy dark-red hair, met his slim dark-haired wife, Bridget Agnes McDermott. One version of the story suggests that Bill boarded at the same house on Plane Street in Newark as Agnes, as she preferred to be called. In the alternative account, Bill accepted an invitation to have dinner one night at the home of a colleague, and Agnes, the host's niece, joined them at the dinner table. Either way, Bill would have known that they came from the same part of Ireland as soon as he heard Agnes's flat midlands brogue. They soon learned they shared an even closer connection. Agnes, born in 1878, had grown up in Castlerea, a town less than ten miles from his hometown. Given their narrowly circumscribed lives, they almost certainly would never have met back in Roscommon.
 Although her father was an illiterate tenant farmer like Bill's, Agnes had finished more years of school than Bill, later telling her children that she scored so high on a national entrance exam, the state offered to pay her way through high school. When her mother refused, based on the notion that girls did not need so much education, Agnes resolved to save up enough money working menial jobs to immigrate to the United States, which she did around 1894, moving in with her aunt in Newark around the same time Bill arrived in the city. Their children knew little about their courtship beyond the fact that Bill and Agnes were married at St. John's Catholic Church in Newark on June 17, 1903. Eight months later Agnes gave birth to their first child, a daughter they named Katherine.
 Around the time that Bill became a father, he started on a well-trod path to Irish immigrant success in early-twentieth-century America: up through union ranks and into politics. A member of Local 55 of the International Brotherhood of Stationary Firemen, Bill initially sought a leadership role in the organization because he thought it was poorly run. Members paid their dues to a saloonkeeper who kept no account of their money and doled out jobs as he saw fit. Bill successfully ran for office, becoming the local's business agent. As a union officer he displayed the qualities that later made him a popular politician: honesty, transparency, and a gregarious personality.

On April 25, 1906, attention in Newark, as in the rest of the country, was focused on San Francisco, where a devastating earthquake had struck exactly one week earlier. Agnes Brennan's thoughts were closer to home that day. Inside the Brennans' wood-frame house at 357 New Street, an unpaved road just beyond downtown, past the Morris Canal and right behind the Daly Hat Company, she went into labor with her second child. Agnes later remembered that someone flagged down the family doctor, named Haggerty, who was on his way to a wedding at nearby St. Joseph's Church and showed up at the house wearing striped pants and a cutaway morning coat. At 1 p.m. Agnes gave birth to her first son, whom they named after Bill.
 As if making up for lost time, Agnes, who was twenty-six when her first child was born, spent more than half of her first sixteen years of marriage pregnant. She gave birth to eight children in all and also suffered two miscarriages. The two following William Jr. were also boys: Charlie, born in 1907, and Tom, born in 1910. Then came two more girls, Betty and Peggy, by the time young William was nine. The Brennans moved frequently, outgrowing their modest lodgings. The future Supreme Court justice spent his infancy in three different rentals around the edge of Branch Brook Park, a multiethnic section of Newark that was a step up from Down Neck. The first house he would remember was at 212 Parker Street, in a predominantly Italian neighborhood just across Bloomfield Avenue from Newark's most affluent section, Forest Hill.
 Despite his union position, the elder Brennan found it difficult to support his ever-growing household, and his long hours proved exhausting. After briefly considering the more lucrative job of operating engineer, Bill ultimately decided to stay in the stationary firemen's union, where he rose to become national vice president and leader of both the Essex County and state labor federations. He began traveling around the country on union business, finding time on one such trip in 1911 to write Agnes a playful postcard from Milwaukee. “Well kitten, I hope yourself + kidlets are well. Will be home Tues. p.m. if allowed, Your Hubby.” That same year, Bill sat behind union president Timothy Healey as he testified on a foreign trade bill before the U.S. Senate Finance Committee.
 Living on the edge of affluence, William Jr. was nevertheless acutely aware of inequality and class differences. As a youngster he was put to work carrying orders for a butcher and recalled being struck by the gap separating the working-class families on his side of Bloomfield Avenue and the upper-class residents of Forest Hill, who lived in stately Victorian and colonial mansions.
 At the age of five, Willie Brennan, as he was then known, went off to school at the Sacred Heart Roman Catholic School. Bill and Agnes sent him to parochial school either out of devotion to their faith or mere convenience, given that Sacred Heart was located on Parker Street, just a couple of blocks from their home. Brennan distinguished himself from an early age as a bookworm, much to his parents' satisfaction. They hoped all of their children would obtain the schooling they never had, which they viewed as the key to advancing beyond their station in life. As the oldest son, Brennan carried the heaviest burden of expectations, although with his high grades he generally had no trouble pleasing his father.
 Bill dominated the household and brooked no dissent from his children. Brennan and his siblings knew to quiet down as soon as their father walked in the door each night. Inspiring respect, Bill resorted to physical punishment only sparingly. Brennan most vividly remembered the instances where he expected to get punished and did not, such as the time he and his younger brothers hit a baseball through a neighbor's window and the neighbor complained bitterly to Bill. “Boy [my father] did tell us off about watching out for people's property,” Brennan remembered. “But that was the end of it.” Brennan feared his father most when Bill drank. Although he could enjoy a beer or two with friends without incident, Bill was inclined to drink alone at home when something upset him at work. “He'd get himself potted, and when that would happen, he was not a very pleasant person to have around,” Brennan recalled. “We'd just stay out of his way.” Those nights of his father's drunken belligerence, seared in his memory, were a troubled foundation for Brennan. Never a problem drinker himself, alcoholism would follow him in his family life.

The elder brennan stood in several inches of slush at the corner of Belmont and Springfield on the night of April 8, 1916, in a downpour of rain mixing with snow. The dreary weather perfectly reflected the dark mood of Bill and his fellow labor organizers as they set out to demonstrate on behalf of striking trolley-car conductors and motormen. Two weeks had passed since a small number of trolley workers had walked off the job, seeking higher pay and a nine-hour day. The Public Service Corporation still refused to recognize the strike. Newark's police department sided with the powerful company, which also controlled the city's gas and electric utilities. Police officers broke up demonstrations and deployed en masse to prevent picketing outside the car barns where trolleys were housed. Union men retaliated by sabotaging at least one trolley car and throwing stones at those operated by nonunion men.
 The Newark police had finally granted the union permission to march, but smothered the parade with squads of mounted police. Almost every last police captain, lieutenant, sergeant, and patrolman in the entire department lined both sides of the parade route. Bill, as secretary of the strike committee, would have harbored no illusions at this point about the strike's prospects. Weeks after the march, Newark began a massive celebration of the city's 250th birthday, but Bill was feeling more anger than civic pride that spring as he was elected president of the Essex County Trades Council. He had learned a bitter lesson about how government power could be turned against the workingman.
 The trolley workers' strike had failed, but Newark politicians recognized organized labor's growing political strength. In early 1917, seeking a labor representative on the board overseeing the police department, Mayor Thomas Raymond offered the post to Bill, who was viewed as a palatable choice to both the unions and the city's business elite. Bill accepted the offer, although his tenure on the police board was brief. Newark overwhelmingly voted in October of that year to replace its mayor and city council with a five-member city commission vested with both executive and legislative power. A month later, Bill ran as the labor candidate in a crowded field of eighty-six candidates under the slogan “Civic representation for working people.” On election night, the 15,736 votes the elder Brennan received was the third highest of any candidate, thus assuring him one of the five seats on the commission.
 Under the new government structure, each commissioner oversaw a separate part of the city government. Bill chose to run the city's fire and police departments as director of public safety. He was as strict a lawman as he was a father. He pledged to vigorously enforce closing times for saloons, dance halls, and cabarets, and docked an officer thirty days' pay for public drunkenness. Yet he also exhibited the same capacity for tolerance he showed with his children, once forgiving a patrolman who stopped him for a driving infraction and then in his zeal insisted on taking Bill to the police station.
 Although there was the potential for corruption in the departments he oversaw, Bill himself, by all accounts, stayed honest. But he was not above enjoying the perks of the job, including the use of a city-owned cabin beside Newark's Pequannock Watershed, which some neighbors criticized as an unnecessary extravagance. He had a chauffeur-driven car at a time when few in the middle class could afford to buy their own automobiles. The job also afforded Bill frequent opportunities to travel. He headed off to annual union and police-chief conventions from Montreal to New Orleans, and took at least one vacation each winter in Bermuda, Cuba, or Miami, Florida. Conscious of his appeal to the common man, Bill took pains to portray these trips as low-cost affairs. Newspaper stories typically described the tropical getaways as an opportunity for the commissioner, who suffered frequent bouts of pleurisy, to recuperate from the health problems that plagued him.
 Bill is not easily defined according to the labels traditionally affixed to Irish Catholic politicians of the time. He was a loyal Democrat, yet avoided close association with the city's party apparatus. Unlike the stereotypical Irish machine boss of the era, he showed little interest in accumulating power or siphoning off a fortune. Bill's campaign slogan during subsequent reelection campaigns, “A square deal for all, special privileges to none,” evoked Teddy Roosevelt's progressive presidential agenda. Once in office, Bill did exhibit liberal tendencies. He warned that police officers who struck defenseless suspects deserved to be dismissed from the force. And he earned the respect of the local chapter of the civil rights group the Urban League by appointing three additional black patrol officers at a time when there was only one African American on the force.
 Bill was a progressive in the mold of the Catholic theologian John A. Ryan, a forceful advocate for social justice who would come to be dubbed the New Deal's priest. Ryan's 1906 book, A Living Wage, argued that workers deserved an income that allowed for a comfortable living, a workday of reasonable length, and insurance that protected them against accidents, illness, and unemployment. Although there is no evidence that Bill read any of Ryan's books, he echoed Ryan's rhetoric when he explained to reporters why he endorsed a pay increase for police and firemen: “This was only a living wage, and I think the men were entitled to it.”
 Bill's liberalism did not extend, though, to his attitudes toward civil liberties. He pledged full cooperation with efforts to suppress the sale of magazines and other publications deemed morally objectionable. His tenure as commissioner coincided with a national crackdown on foreign radicals and suspected Communists, a movement he joined without qualms. He declared that any police officer who did nothing in the face of an insult to the American flag did not deserve to wear the uniform. His union sympathies did not extend to allowing radical labor agitator William Z. Foster to speak in Newark in 1924, and he forbade a protest on behalf of the Italian American anarchists Nicola Sacco and Bartolomeo Vanzetti, who were executed in 1927.
 Bill's most notable crackdown on free speech came in 1926, when he prohibited the showing of The Naked Truth, a silent film in which a father instructs his son about the dangers of venereal disease. The board of censors appointed by Bill had barred Newark's Capitol Theatre from exhibiting the film, concluding that it was not suitable for commercial distribution and could be appropriately shown only free of charge as a public health service, at a YMCA, school building, or church. Bill, who declined an invitation to view the film, threatened to revoke the theater's license and to arrest anyone involved in its exhibition. The decision won praise from Newark's Episcopal bishop, but a state judge issued an injunction barring the commissioner from interfering, on the grounds that he lacked any authority to engage in such censorship.

Not long after joining the police board, Bill had relocated the family to Vailsburg, a suburban neighborhood on Newark's far western edge. Just a few years earlier most residents of downtown Newark considered Vailsburg a place apart, as a destination for leisurely daytrips to the Electric Park amusement park or Velodrome outdoor bicycle track. Vailsburg had recently proved an appealing residential area for upwardly mobile immigrants relocating from the Ironbound. Many of the newcomers were city workers like Bill and the police and firemen he oversaw, who were required to live within the city's borders. The Brennan family moved into a triple-decker house on Alexander Street, their most significant step yet out of the urban ghetto.
 The move to Vailsburg coincided with the end of the younger Brennan's parochial school education. He began attending a public school just up the block from his family's house on Alexander Street. Bill had no intention of circumscribing his children's education to satisfy his church. William Jr. and five of his seven siblings later attended public high school. Only Tom and Betty, viewed as the wild ones, were sent to parochial high schools.
 Like so many other immigrants, Brennan's parents had complicated feelings about their ethnic identities. Bill subscribed to the Irish World newspaper, joined Irish fraternal organizations such as the Friendly Sons of Saint Patrick and the Ancient Order of Hibernians, and treated Saint Patrick's Day as an important holiday. But while he enjoyed putting his feet up on his desk in his City Hall basement office and regaling visitors with tales of growing up in Ireland, Bill divulged little about his childhood to his own family. Agnes was even more ambivalent about her roots. She insisted that her children attend Sunday Mass but told at least one son she did not believe in the Church doctrine of papal infallibility. Agnes bought every one of the Irish tenor John McCormack's Victor Red Seal records, featuring songs such as “My Wild Irish Rose” and “When Irish Eyes Are Smiling,” on the day they went on sale. But she did not want to be known as Bridget, a name closely associated in nineteenth-century America with Irish domestic workers. She was so self-conscious about her Irish brogue that she rarely spoke in front of strangers. And if Bill slipped into Gaelic when talking with friends in their house, she would cut them off by snapping, “You are Americans now!”
 Both Bill and Agnes wanted to retain some links to their Irish roots, but not at the expense of their children identifying fully as American. Brennan internalized his parents' desire to live in both worlds. On the one hand, he insisted later, his identity was inseparable from “the kind of family I was born into and the kind of society,” which he described as “blue collar, Roman Catholic, [and] Irish.” At the same time, he remembered attending Mass as “an agony we went through every Sunday whether you liked it or not.” Having left parochial school at a young age, Brennan retained a relatively unsophisticated understanding of Church doctrine. While he continued to attend Sunday school, he had happier memories of playing pool in the church's recreation room for teenagers.
 Barringer High School, which Brennan attended beginning in 1920, was a prestigious public school and a magnet for the children of Irish, Italian, and Jewish immigrant parents like Brennan's with big ambitions for their first-generation American offspring. Brennan excelled academically, joined the science and Spanish clubs, wrote for the school newspaper, the Acropolis, and, in the first hint of an interest in law, chaired the Constitution Day committee. For much of high school, Brennan was accompanied at Barringer by Charlie, the brother to whom he was closest. They had always shared a bedroom growing up as well as a common sense of mischief, throwing pillows at their sister Betty to get her out of bed in the morning. During Brennan's high school years, the family relocated a couple of blocks to their second home in Vailsburg, a single-family house on North Munn Avenue. Brennan and Charlie went to work together each morning at a dairy farm across the street. Brennan pulled rank as older brother, forcing Charlie to work the earlier shift milking the cows at Martens Dairy while he delivered the bottles later, on his way to school. The family's finances had improved considerably after Bill became a city commissioner. But Brennan continued working after school and on weekends, delivering newspapers, making change for passengers boarding trolley cars downtown, and gassing up cars at a neighborhood filling station. Brennan kept whatever he earned for spending money, allowing him to splurge on his wardrobe. He had developed a taste as a teenager for nice suits and well-shined shoes.
 On Sunday nights, Brennan and Charlie invited friends over for dinner. The house on North Munn was crowded enough even without the additional guests, particularly after the arrival of Brennan's paternal grandmother, who emigrated from Ireland, and the birth of his two youngest siblings: Helen in 1917 and Frank in 1919. Meals at the Brennan household were boisterous affairs where siblings vied to talk about everything from international politics to local high school basketball scores. The girlfriend of one of Brennan's brothers later remembered reading the newspaper from end to end in order to keep up with the conversation. Adding to the lively atmosphere might be Bill's two brothers who lived in New York: Patrick, a firefighter with bright red hair, and Tom, a chauffeur. Still, Agnes never complained. She cooked ham, potato salad, and sheet cake for twenty or more people. After dinner, they rolled up the rug and danced.

Brennan was fifteen years old when his father ran for reelection in 1921, old enough to participate fully in a political campaign for the first time. He witnessed all the theatrics then typical of Newark's city-commissioner campaigns. There were torch-lit parades and raucous rallies at the Newark armory, where the walls shook from the sounds of marching bands and thousands of cheering attendees. Along the way, Brennan also observed his father's ample political skills—the way Bill remembered names and faces and could fit in so comfortably at a firehouse or corner tavern. Bill's up-by-his-bootstraps rise appealed to voters, and every September beginning in 1921, Bill shored up his image as a man of the people by hosting picnics for thousands of city residents, featuring free soda, hot dogs, and ice cream and lollipops, plus merry-go-rounds and toboggan slides. A savvy student of Newark's changing demographics, Bill realized he could not just rely on his kinsfolk at a time when Italians and Russian immigrants outnumbered Newark's Irish residents. He bought ads in the city's Jewish newspapers and touted his Jewish appointments. In subsequent elections, he also reached out to Newark's small black population.
 But Brennan, who spent his adolescence as the son of one of Newark's most famous and closely scrutinized figures, also observed an uglier side of politics. Bill's popularity and political skill could not protect him from harsh attacks by critics unhappy with the less than fervent way he enforced Prohibition. Bill, who had never lived outside the urban “wet” Northeast, had misjudged the support Prohibition enjoyed, particularly in the Midwest and South. In January 1918, even as the first states started ratifying the Eighteenth Amendment outlawing the manufacture, sale, and transportation of “intoxicating liquors,” Bill assured a gathering of liquor wholesalers in Newark that American soldiers fighting in Europe would not tolerate such restrictions on their liberty when they returned home. A year later, just two months after World War I ended, the thirty-sixth and final state needed to ratify the amendment did so. The amendment and the Volstead Act, which spelled out penalties for its violation, went into effect in January 1920.
 There is a certain irony that the elder Brennan, a former brewery worker, wound up with the thankless task of helping U.S. Treasury agents enforce Prohibition. Bill had no intention of forsaking alcohol himself. He could no longer enjoy a beer or two at his favorite tavern around the corner from his house, but he continued to drink alcohol in the privacy of his own home, where, unfortunately for his family, he was more apt to become belligerent when drunk. It would not be until 1927 that Bill publicly confessed at an Elks Club lunch that he would finally give up alcohol, but only on his doctor's orders.
 Bill had much to lose politically by cracking down on illegal alcohol consumption. Prohibition proved unpopular among Newark's working-class immigrants, the owners of hundreds of saloons where they drank, as well as with the city's vital brewing industry. Production had ceased at the Feigenspan Brewery, but its rooftop sign reading “P.O.N.”—an abbreviation for “Pride of Newark”—still lit up every night like a beacon for Prohibition's repeal. Prohibition spawned new forms of lawlessness throughout the country, and particularly in Newark, which earned a reputation as a bootleg capital. Speakeasies sprung up around the city, and speedboats raced out to freighters loaded with bootleg whiskey lingering just off the coast, beyond the three-mile territorial limit.
 Bill had little enthusiasm for Prohibition, but there is no evidence that he was among the countless New Jersey police officers and politicians who took bribes from bootleggers like Newark gangster Abner “Longie” Zwillman. However, this was one issue where Bill could find no middle ground that might satisfy everybody. Protestant church groups and the local chapter of the Anti-Saloon League came down hard on Bill for lax enforcement, insinuating that he was a drunk. In February 1922 members of a coalition of church groups heckled Bill and other city officials at a City Hall meeting and demanded that he resign. Brennan read about the attacks on his father's character and took them to heart. At sixteen, he turned away from politics. “I saw what it did to my father, and I wanted no part of it,” Brennan recalled. “What a filthy business the whole thing was.”

At the time Brennan applied to college in 1923, most American Catholic students attended church-affiliated colleges. He could have walked to Seton Hall, located two miles from the family's house up South Orange Avenue in neighboring South Orange, New Jersey. But Agnes and Bill had their sights set elsewhere for the first member of either of their families to attend college. Both wanted Brennan to head to the Ivy League.
 Agnes thought Bill should go to Princeton, the top school in New Jersey and training ground for the state's Protestant elite. Princeton accepted Brennan, and his high school yearbook even listed it as his destination. But Bill had other ideas. On the eve of the stock market boom that came to define the Roaring Twenties, the loyal union man envisioned his son's future squarely on the side of Wall Street. Knowing little about such matters, Bill relied on the advice of James W. Costello, his close friend and Newark's chief city engineer. Costello had graduated from the University of Pennsylvania, and convinced Bill that that was where his son should go. Bill encouraged Brennan to apply to Penn's Wharton School of Finance and Commerce, as it was known at the time. Having deferred to his father's wishes throughout his childhood, it did not seem to occur to Brennan that he might have a say in the matter.
 It was the fulfillment of Bill's ambitions, if not necessarily his own, when Brennan arrived at the University of Pennsylvania in the fall of 1924 as a freshman in the College of Arts and Sciences. (As a sophomore, Brennan transferred to Wharton, where he was soon joined by his younger brother Charlie.) Only ninety miles separated Vailsburg from the Penn campus in Philadelphia, but the distance must have seemed much greater as Brennan moved into one of the Tudor Gothic-style dormitory houses designed to evoke the campuses of England's Oxford and Cambridge. Yet this grandson of an illiterate Irish tenant farmer had little trouble fitting in at the university founded in 1749 by Benjamin Franklin. Brennan spent less time at the Newman Center, where Catholic students congregated, than at the Delta Tau Delta fraternity he joined, where members with names like Brennan and O'Hara remained a distinct minority. He lived in the Delta Tau Delta house for three years, Charlie joining as well. The Brennan brothers blended easily among the three dozen fraternity brothers who posed for a yearbook picture, looking like underaged bankers in their three-piece suits, striped ties, and neatly folded breast-pocket handkerchiefs. Much to his father's delight, Brennan's grade cards were filled with “distinguished” and “good”—the two highest levels.
 Each summer, Brennan returned to Newark, where he was employed inspecting a city contractor's street-paving work. He could thank his father's friend James Costello, the city engineer, for the job. It paid well-forty dollars a month, in Brennan's memory, which allowed him to indulge in his preferred high-priced “collegiate” style of dress. He bought $75 custom-made suits and a $105 overcoat he particularly cherished.
 Brennan probably wore one of his fancy handmade suits in December 1926 when he attended one of the big events of Newark's Christmas social season: a cotillion at the East Orange Women's Club. Brennan at the time was a boyishly handsome twenty-year-old, with a thin face and hair neatly combed and smoothed with pomade. His most notable feature was his bright green eyes. Brennan noticed a slim blue-eyed brunette he had never seen before and got up the nerve to approach her. Nineteen-year-old Marjorie Leonard had come to the cotillion with another young man as her date, but added Brennan to her dance card. Brennan was slighter in build and shorter than the lifeguard types who typically pursued her, but Marjorie thought Brennan was handsome, intelligent, and a good dancer. They also shared common Irish Catholic roots and grew up only a couple of miles apart, although Marjorie's childhood had been markedly different from Brennan's.
 Marjorie's American-born parents came from Belfast, a small town in western New York State best known as where the Irish boxer John L. Sullivan had his training camp. Her father, Hugh Leonard, became a protégé of Sullivan and his trainer, and began wrestling professionally at age sixteen. By the time Marjorie was born, Hugh had become a famous coach at the elite New York Athletic Club and author of an illustrated handbook on wrestling. But when Marjorie was seven years old, Hugh was killed at his summer training quarters in Belfast, struck by lightning when he ran outside during a storm to take a flag down. Her mother, Rose O'Boyle, died when Marjorie was a teenager, leaving Marjorie an orphan under the care of her three older sisters. After graduating from Orange High School, she went straight to work in a clerical job at the New York Insurance Company and lived in an apartment in Orange with Irene, the sister roughly fifteen years her senior who had become her surrogate mother.
 Brennan, the Ivy League fraternity brother, was instantly smitten with this vivacious, independent, and strong-willed young woman. He soon began writing Marjorie almost every day. She visited Philadelphia when his fraternity hosted formal parties. Eventually, Brennan brought Marjorie home to meet his family. Having had a different experience of family life growing up, Marjorie seemed uncomfortable at the Brennans' animated dinner table. But she could certainly hold her own with Brennan. During their courtship, Brennan gave Marjorie a fraternity pin, an expensive symbol of commitment. In the middle of an argument they had on a Newark trolley car, she threw it out the window. They looked at each other, equally in shock at what she had done, and got off the trolley at the next stop to search for the pin, which was nowhere to be found.
 There was little question about what Brennan would do after graduating college, at least in his father's mind. Long after he had become a successful attorney, Brennan remembered his father encouraging him to pursue a legal career as early as high school. In fact, Bill had envisioned a business career for his oldest son when he encouraged Brennan to apply to Wharton. But, as with Brennan's college choice, Bill's thinking about Brennan's career was heavily influenced by a friend's advice. Jerome Congleton, Newark's city counsel and then mayor, suggested that, as a graduate of a top law school, Brennan could easily find work as an attorney on Wall Street. Brennan finished college in the spring of 1928 at a time when stocks soared to unimaginable new heights every day, and the entire country seemed caught up in a speculative fever. Once again, Brennan's own preferences about his future seemed immaterial.
 Brennan, most likely with Bill's considerable input, chose as his destination Harvard Law School, the oldest continually operated law school in the country and, by the time he applied, also the nation's preeminent one. Gaining admission to Harvard Law was not quite as singular an achievement in Brennan's day as it became later. Applicants needed to present little more than a diploma from a reputable college and a deposit toward the $400 annual tuition. The tough part, as these newcomers learned, was the culling that occurred following exams at the end of the first year. Roughly a third of students who arrived under this open admissions policy received letters the summer after they took their first exams telling them not to come back.
 Five weeks before graduating college, Brennan engaged in the first rebellious act of his life. He and Marjorie decided to elope. They traveled to Maryland, which had no waiting period for a marriage license and required only a church ceremony. William Mackessy, the priest they approached at a Catholic church in Baltimore, seemed suspicious. “Why aren't you getting married at home?” Brennan recalled Mackessy asking. Brennan, then twenty-two, and Marjorie, twenty-one, did not want to tell the priest that they feared Bill would disapprove of the marriage. Brennan suspected his father would say they should wait until after he graduated law school and could afford to support a wife.
 But after a year and a half of dating, neither of them looked forward to being apart for three more years without any formal commitment. Marjorie was the more devout Catholic, having turned to her faith for solace during her traumatic childhood. But she was not about to let the priest interfere with their plans. So when Mackessy wavered, they threatened to head to one of the private chapels in Elkton, a small town in the northeastern corner of Maryland, at the time considered the elopement capital of the East Coast. The priest finally relented and married them, after rounding up as witnesses a couple of women praying at the church. Brennan's first rebellious act was an incomplete one, however. At the age of twenty-two, he still could not openly defy his father, and opted to keep the marriage a secret. Brennan graduated college on June 20, 1928, his family having no idea that he was a married man.

Marjorie stayed behind in New Jersey when Brennan headed to Cambridge, Massachusetts, in September 1928 to begin his first semester at Harvard Law School. He was as unaccustomed as the rest of his roughly seven hundred classmates to the unique style of instruction they encountered in the school's amphitheater-shaped classrooms. A half century earlier, Dean Christopher Columbus Langdell had abandoned textbooks and lectures in favor of having students read legal opinions collected in casebooks and answer questions in a Socratic dialogue, using close questioning to tease out the facts of the case and relevant rules of law. This case method helped burnish Harvard Law School's reputation and made it a model for legal education throughout the country. The curriculum had changed little in the intervening years. First-year students were divided into four sections, and enrolled in civil procedure, contracts, criminal law, property, and torts. For Brennan and his classmates the system had one advantage: with a class size of 168 students, no one could get called on too frequently.
 Brennan found lodging at a nearby boardinghouse in Harvard Square along with a group of other students. As at Penn, he had no trouble fitting in among his classmates. He became close friends with his fellow boardinghouse residents, including fellow New Jersey native Bill Lord, a graduate of Dartmouth College whose father was president of the Scribner publishing house. But not even his closest law school friends knew Brennan was married. They knew Marjorie only as the girlfriend to whom he wrote long letters while the rest of them went out on dates. During her occasional visits, Marjorie stayed at a Boston hotel for the sake of appearances.
 For Brennan and his law school friends, studying took up much of their time. The pressure was intense, perhaps explaining why Brennan smoked cigarettes heavily during his Harvard years. His work paid off. In his second year, Brennan scored high enough to qualify for one of the three organizations reserved for top students. The Harvard Law Review, a prestigious student-run journal, invited the highest-scoring dozen or so students; the Board of Student Advisers took the second-best group; and the third batch qualified for the Legal Aid Bureau, which Brennan was invited to join when he returned in the fall of his third year.
 Founded in 1913, the student-run Legal Aid Bureau helped Cambridge's poor with landlord-tenant disputes, domestic relations, and personal-injury cases. Brennan was exposed for the first time to real-world legal problems and the plight of the poor. He later credited the Legal Aid Bureau with opening his eyes to law's “compassionate aspects-helping confused and worried little people over problems of rent and family and small inheritances-problems of little or no significance in the large, but which can assume terrifying proportions for the people concerned.” Membership in the Legal Aid Bureau put Brennan a notch or two below the top of his class, although the hands-on nature of the work probably suited him better than the more academic-minded Law Review anyway. Brennan never showed much interest in theoretical debates or the schools of legal thought developing at the time. He was not anti-intellectual, but he largely considered his education at Wharton and Harvard Law School a means to an end rather than an intellectual exercise to be enjoyed for its own sake. He later recalled his college auction-bridge games in much more vivid detail than any books or authors he read in college or law school.
 It was his father who had always had the most influence on Brennan. He had learned to sympathize with the underdog as he watched his father's struggle as a labor leader at a time when, Brennan recalled, society “wanted no part of organized unions.” He had soaked up his father's concerns about government power being employed against individuals, as it was during the 1916 trolley workers' strike, and he also saw how government could be a force for good during the thirteen years his father served as a city commissioner. But unlike his father, Brennan's liberalism extended beyond economic matters to issues of civil liberties. And that enlarging upon his father's views may well have begun at Harvard Law School, in a course taught by Professor Zechariah Chafee.
 Shaken by the government-sanctioned repression of speech during World War I, Chafee responded by writing Free Speech. Published in 1920, the book became a must-read for lawyers grappling with how to strike the proper balance between liberty and the sorts of restraints imposed on speech during emergencies such as wartime. Brennan recalled that it was in Chafee's class on equity during his second year in law school that he first thought seriously about what sort of protections the First Amendment afforded. (Brennan did not enroll in constitutional law, an elective class taught by the renowned scholar Thomas Reed Powell, although he recalled sometimes sitting in on the lectures.) In one class, Chafee spoke excitedly about an unusual free speech case he had come across. Brennan did not realize until the end of the discussion that Chafee was praising the New Jersey state court decision overturning his father's prohibition of the film The Naked Truth. Brennan recounted the story to Bill during his next visit home. His father was not amused.

The depression caught Bill—like most Americans—completely by surprise. He had campaigned for a fourth term on the city commission with the slogan “Continued Prosperity” in the spring of 1929. Everything began changing after the stock market crashed that October, although the devastation was relatively slow to reach Newark. It was not until early 1930 that employment and wages began to decline steadily. Bill's government job meant that the Brennan family did not have much to worry about in the first winter of the Great Depression. They were more concerned about Agnes, who underwent surgery to repair an intestinal blockage in January 1930.
 Bill, now fifty-eight, his red hair long since gone gray, continued to struggle with health issues as well. He had been plagued with kidney stones for at least a year, and after the latest attack in May, Bill's doctor had suggested a few days of quiet recuperation. Bill retreated to his city-owned cabin at the Pequannock Watershed for a week, but wound up catching a cold. When a fever he developed worsened, his doctor retrieved him from the cabin, and Bill was admitted to the hospital on May 12.
 The next day, the Newark Star Eagle reported that the commissioner was in “very serious condition” with pneumonia in both lungs. His doctor predicted Bill would “pull through,” but overnight his condition worsened, and he lapsed into a coma early on the morning of May 14. After receiving a call in Cambridge from his family, the younger Brennan frantically tried to find a way back to Newark. His law school friend Bill Lord drove him to the train station, but too late for the departure. He then missed the next available flight out of Boston, and by the time he finally arrived home by plane, it was too late. Bill had died at Newark's Presbyterian Hospital at 10:23 a.m., surrounded by family, including his seventy-seven-year-old mother, Elizabeth, as well as his wife and two of his oldest children, Katherine and Charlie. That night, Bill's body was returned to the Brennans' Munn Avenue home, where he remained overnight. Fourteen years after Bill had marched through the streets of Newark surrounded by hostile mounted policemen, officers escorted Bill's casket through the streets to City Hall, where he lay in state. On May 16, as the funeral Mass began, flights at Newark's airport and traffic downtown halted to observe a moment of silence in his honor.
 The outpouring of affection and grief reflected Bill's extraordinary popularity and reputation for honesty. He died at his peak politically, perhaps fortunate not to live long enough to see the city government he helped lead become the target of public anger. Voters were to cast out all but one of his fellow city commissioners in the next election in 1933 amid accusations that several had bought parcels of land later sold to the city at inflated prices. Nor did he live long enough to see his greatest ambition realized: three of his sons accumulated a total of five Ivy League degrees, and two of his daughters attended college too.
 A month after Bill's death, the family suffered another loss when Bill's mother, Elizabeth, died. Bill had left Elizabeth $2,000; the remainder of his estate went to Agnes, who could use whatever financial help she could find. Four of Brennan's siblings still lived at home at the time. Betty and Peggy were in high school, and Helen and Frank were still in grade school. Charlie was still in college at the University of Pennsylvania, and Brennan had a year remaining in law school. The City of Newark offered some assistance, and Brennan's older sister, Katherine, who was working at Prudential, chipped in too.
 Prior to his death Bill had used his connections to land his oldest son a summer clerkship at one of Newark's leading law firms. Despite high grades at a top law school, Brennan was not the type of candidate the firm of Pitney, Hardin & Skinner usually selected. John O. H. Pitney and John R. Hardin, two Princeton graduates born in 1860, had founded the firm in 1902. Pitney's brother, Mahlon, was a justice on the U.S. Supreme Court, and two of his sons had helped build the law practice into the firm of choice for New Jersey's top corporations and banks. Like its founders, every Pitney Hardin partner had graduated from Princeton. And none were Catholic. But Bill's colleague on the city commission, Mayor Congleton, had intervened on Brennan's behalf at the firm, nicknamed “Pluck'em, Hook'um & Skin'um” in reference to its aggressive representation of corporate clients.
 Congleton's request came as a surprise, according to one of the firm's partners, Waldron Ward. The partners did not necessarily agree with Bill's politics, but Ward recalled they regarded him “as a rugged, honest and able man.” Left unstated was the potential future benefit of doing the mayor a favor. Brennan was offered a summer position. He later remembered little about the summer except that it went well enough that eventually he received an offer to join the firm upon graduation.

Brennan faced the challenge of financing his final year of law school without his father's help when he returned to Cambridge in the fall of 1930. He obtained a scholarship from the school and got a job waiting tables at a boardinghouse, although his standard of living remained high enough that he soon felt free to quit the job. Most people did not have that luxury in Newark, where employment at major manufacturers had fallen 25 percent and residents who could not afford to heat their homes filled wheelbarrows and any available conveyance with cords of wood given away at a city firehouse. Brennan, by contrast, could still afford to see plays and lectures in Boston or dine at his favorite restaurant downtown, Durgin Park, with his law school friends.
 Every Monday and Tuesday, Brennan headed to Langdell Hall at 11 a.m. for a course called Public Utilities. The name was a bit of a misnomer, since the instructor felt free to lecture about whatever he pleased, with tangents into politics, economics, philosophy, and history. Five hours of class elapsed before the professor even turned to the first case, examining how the Interstate Commerce Commission regulated railroads. Then he lingered on that one case for a month and four days, dissecting it in such depth that students nicknamed the class “The Case of the Month Club.” Felix Frankfurter was trying to show the two hundred assembled students how law was shaped by outside forces rather than something to be studied in isolation.
 This forty-eight-year-old professor's biography was as unique on the Harvard faculty as the course he taught. In 1894, at age twelve, he had immigrated to the United States from Austria with his parents and five siblings, settling among other Jewish newcomers on Manhattan's Lower East Side. Despite being a latecomer to English-language instruction, he managed to graduate from City College by the age of nineteen and then to enroll at Harvard Law School, where he was first in his class all three years. His success explains why Frankfurter developed what he admitted was a “quasi-religious” attachment to Harvard Law, which to him embodied the American ideal of meritocracy. Frankfurter did not feel the same way about the New York law firms that would not consider him for a job because he was Jewish. He returned to Harvard Law School as a professor in 1914 and remained active in liberal politics. Frankfurter emerged during the 1920s as a leading crusader on behalf of civil liberties. He was denounced as a radical for his vigorous defense of Sacco and Vanzetti, the Italian American anarchists for whom Brennan's father refused to allow even a protest meeting in Newark.
 Brennan, like so many of Frankfurter's students, found both the charismatic professor and his class fascinating. But he was not in the elite circle of top students Frankfurter took under his wing in this era, ranging from Brennan's classmate and future Harvard Law professor Paul Freund, to Dean Acheson, the future secretary of state, to Alger Hiss, later accused of being a Soviet spy. Frankfurter invited these favored few to enroll in his more intimate seminars and to join him for Sunday-afternoon teas at his Brattle Street home near campus. In his domineering way, Frankfurter remained absorbed in his disciples' lives long after they graduated. Brennan, at the time, was unworthy of Frankfurter's attention and forgotten as soon as he graduated in June 1931.

Close to graduation, Brennan finally came clean about his secret marriage. He'd had no trouble telling his law school friends; the difficulty was in explaining things to his mother. Brennan had dug himself into a deep hole by hiding the marriage for so long. So instead of admitting the truth, he schemed to cover it up by arranging a second wedding ceremony.
 Brennan informed his mother that he intended to wed Marjorie, neglecting to mention that they were already married. The trouble started when Brennan went to St. Joseph's Church to pick up a copy of his baptismal certificate while his mother waited outside. “What do you want this for?” asked the skeptical priest, a longtime friend of his father's. Brennan feigned innocence in explaining his intention to wed. “What'd you do with the wife you married in 1928?” the priest replied.
 Unbeknownst to Brennan, Father Mackessy, the Baltimore priest who had performed his and Marjorie's wedding, had sent a copy of the marriage certificate to the churches where Brennan and Marjorie had been baptized. Caught in his lie, Brennan left the church and sheepishly admitted the truth to his mother. “That day was a long, long day,” Brennan recalled. The priest at Marjorie's church proved more understanding and offered to go ahead with the ceremony. Agnes would not hear of it. “No more skulking around!” she ordered. His mother had taken up the mantle of family monarch after Bill's death, and Brennan had no intention of arguing with her. So instead of a second ceremony, a wedding announcement noting the “secret marriage” ran in the Newark Evening News on June 20, 1931. That morning, Brennan and Marjorie set out for a honeymoon in Canada with a stop in Belfast, New York, where Marjorie's parents had grown up.