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  There was, however, a man in town who caught her eye, a thirty-seven-year-old bachelor named Charles Prentiss Bentley. He was a long-faced, jug-eared man with a strong chin and intelligent eyes. The son of a Baptist minister, he was the direct descendant of a dissident English clergyman who had arrived in Boston Harbor in 1637. His ancestor had preached from the pulpit of the church attended by Mary Charlotte’s ancestor Roger Tyrrell.

  Charles Bentley had spent his early adulthood trying to distinguish himself in a career outside the church. He was still trying. He had worked in New York City for a number of years, moving from one dry-goods establishment to another, while also serving on the staff of the Dry Goods Economist, the leading trade paper in the industry. At the end of 1900, he moved to New Milford to take over management of C. H. Booth’s store on Bank Street. Booth had been selling everything from clothing to carpets, hats to “fancy crockery,” from a small establishment just off the town green for more than forty years. It was time, he told his customers in a letter published in the local newspaper, to “lay aside some of the care and responsibility of business.” In January of 1901, the store was renamed Booth & Bentley Company, with Charles the junior, but more active, partner.

  The schoolteacher and the merchant wed in the spring of 1907, setting up their home in one of the well-kept, clapboard houses on Terrace Place, a lovely, tree-lined street near the center of town. The homes were not grand, but the street was one of the most respectable in town, home to a number of long-time New Milford residents. It was here, on January 1, 1908, almost exactly nine months after their wedding, that Mary and Charles welcomed their first and only child, a daughter, whom they named Elizabeth Turrill Bentley.

  Mary’s life, still lived in the comfortable confines of her home-town among her large, stable family, nonetheless changed dramatically. She had been a self-supporting career woman. Now she was a mother and the wife of a man who was fast becoming, or trying to become, one of New Milford’s leading citizens. Charles had taken on civic responsibilities, acting as a committee chairman for the town’s bicentennial celebration during the summer before his daughter’s birth. He donated, with some fanfare, a large American flag that was ceremoniously hoisted up a new eighty-foot flagpole constructed on the town green for the occasion. He worked hard at Booth & Bentley, using his knowledge of jobbers and manufacturers in New York City to bring new merchandise to the store. He advertised aggressively, tempting customers with inventory sales, Christmas sales, spring sales, and half-price sable fox neckpieces. But Booth & Bentley was one of a half dozen dry-goods stores serving the area, and there just wasn’t enough business to go around. Old Mr. Booth was quite old by then and, although Charles had taken over the daily operation of the business, Booth didn’t want the responsibility of ownership in his dotage. When Elizabeth was just about to start grade school, the store was sold to a Danbury businessman, leaving Charles temporarily unemployed.

  But Charles Bentley was a man accustomed to the vagaries of employment. Early in 1914, he signed on as business manager of a new weekly newspaper, New Milford Times, which promised to serve “every man, woman, boy and girl in the community” and run competition to the already established Gazette. “Tell It to the Times; We Tell It to the People” was the spirited motto. The paper seemed to flourish under Charles’s management, offering a lively compendium of local news with a healthy dose of advertising. But less than a year and a half after taking the position, Charles left, and in 1915, when Elizabeth was eight and just finishing second grade at Center School, the Bentleys moved to Ithaca, New York, where Charles had apparently secured a position at another store. Elizabeth would leave behind not only her school companions and Terrace Place neighbors but also her grandparents, her many aunts, uncles, and cousins—the entire Turrill clan. It would have been a difficult move for any little girl. But for Elizabeth, who had inherited her mother’s quiet temperament and studious ways, it was especially so. It was not easy for her to make friends, and the sudden move to a new town in a different state didn’t help. Ithaca, it turned out, was only the first of many moves that would disrupt her childhood.

  The Bentleys lived in western New York for barely two years before the peripatetic Charles, always looking to better himself, moved the family down to Poughkeepsie and then, three years later, in the summer of 1920, to McKeesport, a western Pennsylvania steeltown. While Charles was alternately finding and losing his occupational footing, Elizabeth attended four different grammar schools in five years. It was a lonely childhood spent reading books and following the stern dictates of her mother, who, regardless of where they lived, focused on giving her daughter an old-fashioned New England upbringing. Elizabeth may have chafed under the rules, but her mother was her role model. From as early as she could remember, Elizabeth Bentley wanted to be a schoolteacher.

  Life in McKeesport, just south of Pittsburgh, couldn’t have been more different than her first seven years in peaceful, prosperous New Milford. McKeesport in 1920 was in the throes of a post–World War I depression, with steel mills shut down, hundreds of men out of work, and families homeless and hungry. Evidence of poverty was everywhere. Even if it were possible for a twelve-year-old bookworm to miss what was going on around her, Elizabeth was made directly aware of the problems of McKeesport when her mother began volunteering at a small, private relief agency in town. Every afternoon, Mary would come home weary and grim after a day of visiting tenements, listening to sad stories, and dispensing the little aid made available to the agency by local donors.

  One evening she returned white-faced and shaken. She had spent the afternoon investigating conditions at a filthy tenement whose rickety stairs had collapsed and injured one of her clients. Back at the agency office, Mary discovered that the owner of the building was a leading citizen of the community, a wealthy man who sat on the executive board of the relief agency. With one hand, he had donated money to the agency. With the other, he had extracted rent payments for deplorable housing from families who could barely afford to feed themselves.

  How could anyone be so greedy for money that they’d make it that way? Mary asked her daughter. A rock-ribbed Republican, Mary made a connection for Elizabeth that the girl would not forget: the greed of the wealthy tied to the poverty of the working class. But Mary was not a political person. She dealt with the problems she saw in quiet ways. She worked for the relief agency until it ran out of money. She invited people into her home to eat hot meals. She nursed the sick. Meanwhile, Elizabeth finished eighth grade in McKeesport, graduating first in her class and earning the top award, the Golden Eaglet, in Girl Scouts. She started high school, but at the end of her sophomore year, the family moved again, for the fourth time, to Rochester, New York.

  In Rochester, Charles Bentley finally found a stable—and quite lucrative—position as general superintendent of McCurdy & Company, a large, fashionable, downtown department store. Mary took a job as an eighth grade teacher. The family moved to a new home on East Avenue in a respectable neighborhood south of downtown. All along East Avenue, a half-mile to the north, were the mansions of Rochester’s elite. This is where George Eastman, of Kodak fame, lived. The Bentleys were not of this class, but Charles’s new job meant they were living better than they ever had before. Elizabeth enrolled for her final two years in East High, a big, imposing school with a junior class larger than the entire eight grades of New Milford Central. It would have been easy for her to get lost there, a new girl, quiet and bookish, wandering the long corridors of the massive three-story building. But she made an effort to become involved in high school life. She played field hockey during her junior year and also joined the swimming and riding clubs. As a senior, she joined the Literary Club and worked on The Orient, the school’s yearbook. She tried hard, but she remained essentially a loner. She had a nickname, “Terry,” a playful, lighthearted name that belied the serious, almost dour young woman she had become. She stared out from her senior picture, her eyes guarded under heavy brows. Her dark brown
hair hung short and straight. Her lips formed a thin, taut line. She looked both resolute and unhappy.

  Partway through her senior year, Elizabeth decided to cut back on her extracurricular activities. She wanted to concentrate on academics, raise her already laudable grades so that she could qualify for a college scholarship. She wanted a good college education, one that would prepare her for a position teaching school, like her mother. She set her sights on Vassar, in Poughkeepsie, New York, an elite school with an elite price tag. Tuition and residence fees totaled $1,000 a year, a sum that exceeded the financial wherewithal of her parents, even with their respectable jobs. She studied hard her senior year, shunning both school activities and any social life she might have had. In the spring of 1926, the good news came. Vassar would award her a scholarship covering half her yearly expenses. She would enroll in the fall.

  Chapter 2

  Sad Sack

  OUT OF THE one million babies born in 1908, it is the happy fate of 337 to attend Vassar [as the] class of 1930,” the esteemed Professor Mills told Elizabeth Bentley and her classmates when they gathered in the college chapel for the fall 1926 convocation. The faculty took places in the choir, dressed in colorful academic robes. The senior class marched in procession to the side pews, in premature caps and gowns. The freshmen, wide-eyed and white-gloved, sat in front listening to the professor exhort them to live their lives not as “Flaming Youth”—a reference to the lurid, “Roaring Twenties” depiction of their generation—but as “youth aflame with zeal for all that is self-sacrificing, beautiful, noble, spiritual.”

  You are a privileged group, Professor Mills told the Vassar girls. And he was right. Few girls went to college those days, and fewer still were admitted to what was considered to be one of the country’s most elite women’s colleges, an institution that prided itself on delivering an education equal to the best of the men’s Ivy League, a school that called its graduates “a breed apart.” But with the privilege of going to Vassar, the professor was careful to remind them, came a great obligation, an obligation to live a meaningful life.

  The college was a lovely, brick-and-ivy place. Just seventy-five miles north of Manhattan, it was in a rural, Hudson River Valley world of its own, with a graceful, grassy, old-fashioned campus established in the years before the Civil War. The library looked like an English cathedral. A number of the buildings, impressive, Elizabethan structures of brick and stone, were courtesy of Vassar’s most famous and generous trustee, John D. Rockefeller. Although its reputation for rigorous intellectual pursuits was well established, Vassar was, in other ways, a typical aristocratic female academy, patrician, mannerly, and genteel, with rules and regulations, proscribed behavior, codes of etiquette. Every Thursday afternoon, from four to six, the president and his wife hosted a formal tea at their campus home for the freshman girls. Every evening after dinner, there was mandatory chapel. After seven, no girl could be seen in the company of a man unless the couple was escorted by an approved chaperone. There was no riding in cars, no smoking in public, no inappropriate dress, no indecorous behavior, no unladylike language. Yet under the surface, Vassar brimmed with female intrigue, intense friendships and intense rivalries, confidences sought and betrayed, shifting allegiances, competition and jealousy, relationships both platonic and otherwise. There was a rich emotional texture to life at Vassar for those who lived it fully.

  College life meant rites and traditions, proms, plays and parades, grand marches, the selection of class trees, the ice carnival, Founder’s Day, the passing of Chinese lanterns. In a popular spring ritual, twenty-four of the most popular girls, dressed in white heels, white pleated skirts, and long-sleeved white blouses, paraded across campus with a one hundred–foot garland of daisies draped over their shoulders. Vassar girls could participate in any number of activities from the drama club to the field hockey team, from the debate society to the birdwatching league. There were foreign-language clubs, political clubs, glee clubs. There were opportunities to write for the college newspaper, the college magazine, the yearbook. There were opportunities, every day for four years, for the girls of Vassar to build a close, female society, to form the friendships and the attitudes that would define the rest of their privileged lives.

  Elizabeth Bentley started her life at Vassar in a room on the second floor of Lathrop House, one of a matched set of four dormitories built around a grassy quadrangle. Her room, a single, faced north away from the quad, away from campus and into the dark woods. The light coming through the windows was thin and weak. Elizabeth kept to herself. She made no close friends and shunned the rich mix of rituals and activities that made up campus life. She joined only one club during her four years at Vassar, and that for just a few months. She played no sports. She attended neither her junior nor her senior proms. She majored in English and minored in Italian, also taking a number of French classes. But if she spent her solitary time at Vassar studying, it was not reflected in her grades, which were steadfastly mediocre. Elizabeth Bentley, the scholarship student, the brainy girl who had graduated first in her eighth grade class, was a C-plus student at Vassar. At various points in her college career, she received Ds in English, Italian, and Latin. In studies as diverse as chemistry, history, and drama, she was a C student. She excelled at nothing.

  The work was undoubtedly challenging, and competition from classmates at such an elite school could have been fierce and intimidating. But Elizabeth’s lackluster performance at Vassar probably also had something to do with her general mental health, with the energy and enthusiasm she was unable to muster in living her everyday life. Perhaps her solitary, standoffish ways were a symptom of depression or maybe they were a result of it, but either way, she was not a happy person. At Lathrop House, she was known simply as “Bentley,” probably a function of the fact that there were twenty-six Elizabeths in the class of 1930 but also perhaps an indication of the distance she kept from others. There would be no engaging nickname for her, as many of the girls had. She was, in the eyes of one of the other Elizabeths, a girl who lived across the hall from her during freshman year, a plain, dull, lonely girl, listless and pitiable, a sad sack who, the other Elizabeth was quick to point out, didn’t have a single boyfriend.

  But even Elizabeth Bentley, for all her reclusive ways, could not have been unaware of the maelstrom of provocative ideas circulating around Vassar in the late 1920s. Underneath its finishing-school veneer, with its teas and proms and daisy parades, Vassar was alive with the progressive ideas of the decade. College president Henry Noble McCracken, a liberal thinker and an ardent women suffragist, promoted the notion that political indifference was a “mental defect” and made sure that the intellectual foment of the time found full expression in the lecture halls on campus. During Elizabeth’s freshman year, there were campus lectures on the Equal Rights Amendment, the World Union movement, and “Racial Understanding for Negroes.” There were mass meetings to discuss world issues like the British coal strike and the China “situation.” In her junior year, the president of the American Federation of Labor headlined a weeklong roster of “Economics Week” speakers. In her senior year, there were lectures by social critic Lewis Mumford, historian Will Durant, and Socialist Party presidential candidate Norman Thomas, who had also visited campus the year before Bentley enrolled. Civil rights leader W. E. B. Du Bois came to speak on racial segregation. Socialist and pacifist Scott Nearing lectured on Soviet Russia. And, amid the Granddaughters Club (open only to those girls whose mothers were Vassar graduates), Le Cercle Français (French Club), and the Classical Society (which featured productions by students of Greek and Latin) was the campus chapter of the League for Industrial Democracy (LID), a left-wing, reformist group whose motto was “production for use not for profit.” The campus group, which was small but active, was home to student progressives, socialists and communists alike.

  Although she felt no affinity to any particular left-wing party and did not consider herself a political person, Bentley joined the Leag
ue. Its philosophy—that greed and profit-grabbing underlay much of the suffering of the world—was the view espoused by her own mother, the hard lesson Mrs. Bentley had learned working with the poor in McKeesport. This did not seem like radical or revolutionary thinking to Elizabeth. It was common sense. It was what her mother told her. But she quickly lost patience with the group’s endless discussions of social ills. Everyone seemed to know what was wrong with the world, but no one knew what to do about it. She found her LID compatriots to be impractical dreamers with no plan, no goal, and no vision. Later, she would say that her years at Vassar had served to expose her to so many social injustices that she came away feeling that democracy had failed. She was, she said, left high and dry, not believing in anything.

  But some who came to speak at Vassar did have a vision. They talked about what was considered by many forward-thinkers to be the greatest social experiment of the day, a political philosophy that redefined the individual, reordered society, and revolutionized everyday life. The Bolshevik Revolution was not even ten years old when Bentley started college, and both the causes of the uprising and its outcome were topics of intense interest and debate. Russian counts and barons came to Vassar to give talks about pre-and postrevolutionary education, philosophy, and legislation. Homegrown socialists touted the ultimate triumph of communism over capitalism. Three Vassar professors who had recently visited Russia came back to report improved education for peasants, improved conditions for factory workers, and, as Professor Drake told his youthful audience in the fall of 1928, “a seriousness of purpose, a widespread earnestness.” To drama professor Hallie Flanagan, Russia was a living stage upon which a mighty social drama was being enacted. She called it a struggle against disease, dirt, poverty, and ignorance. More than anyone else at Vassar, Hallie Flanagan was a true believer. She opened many eyes at Vassar, including those of Elizabeth Bentley.