CHAPTER TWO WESTCHESTER 
1966–1977
Carolyn, with her older twin sisters, Lisa and Lauren, had set the kitchen table with a bright multicolored tablecloth, perfect for the cake—lemon, Carolyn’s favorite. Surrounding the table were boxes upon boxes that Ann, the girls’ mother, was still sealing as she found the candles and located the ice cream. The room was bedecked with birthday decorations in the garish primary colors of the late seventies, in marked contrast to Ann’s elegant furnishings. She had refined taste, eschewing the muddy brown and avocado green then overtaking homes across the United States. As soon as the celebration was over, she would start packing again.
It was January 7, 1977, Carolyn’s eleventh birthday. Ann was worried about a move in the middle of the school year. She had been a single mother for a lot of their childhood. Her three girls had enormous reserves of strength, humor, and care—but still. The twins loved to dote on Carolyn and her friends, and with their help the cheer of birthday festivities might help distract her youngest from the fact that this was also a goodbye party.
Carolyn’s whole class had been invited because Ann was the type who knew that the chaos incurred by hosting twenty children on a sugar rush was preferable to hurting the feelings of a child who might otherwise not have been invited. This was one of the lessons she taught her daughters: Never forget about those who are left aside.
Only as the guests departed did it sink in for fellow eleven-year-old Jane Youdelman that this was more than the end of a party. Eleven is an age where you can still ignore the inevitable outcome of certain actions—a house full of boxes means it will soon be vacated—until the moment is thrust upon you. After Carolyn had blown out the candles, the cake had been eaten, and the sun had begun to set, Jane stomped and cried around the perimeter of the Bessette home that was perched on a corner hilltop in White Plains, New York. The day, the year had ended, and her best friend was moving away. Was Carolyn as upset by the move as Jane? Was she excited about living in Greenwich, full stop, or did she feel slight apprehension mixed with joy at the lark of a new adventure? Carolyn, a child who usually bounced with exuberance, held a placid smile on her face amid the shouts of birthday and bon voyage wishes, her emotions concealed behind calm composure.
Jane and Carolyn shared a sense of freedom and joy in their young lives. Over the six years they had been friends, they’d run wild and free around their small White Plains neighborhood. Carolyn always made Jane feel welcome at her home and stood by her in the school hallway to stave off barbs coming from Jane’s older sister, who wasn’t as kind as Lauren or Lisa. Jane found herself writing in her third-grade diary, more than once, “I wish Carolyn was my sister.” The sentiment was widespread among friends; Carolyn was sensitive and highly attuned to her peers.
Yuma Euell, who noticed Carolyn’s kind nature early in their days at school, was also at the party. “I wasn’t in Carolyn’s class that year,” recalled Euell. “But she went out of her way to invite me. She made sure you knew she was your friend.
“She was beautiful and strong, emanating a kind of light around her, but at the same time delicate,” Euell said. “Mrs. Bessette was a substitute teacher at Richard J. Bailey School and friends with my mom. She had called my mother to say Carolyn wanted to ensure I was there because they were leaving the next day. My mom briefly sobbed when Mrs. Bessette told her the news. She always said that Carolyn and Mrs. Bessette were wonderful people.” That the move surprised a few of their friends perhaps had to do with Ann having just sold her half of the house to her ex-husband.
INITIALLY, THE FAMILY LIVED in an apartment at 16 Fieldstone Drive in Hartsdale in Westchester County, New York. Then, on July 1, 1969, when Carolyn was three and a half, they bought the modest three-bedroom house at 12 Old Knollwood Road in White Plains, a ten-minute drive from Rex Ridge.
Neither Hartsdale nor White Plains was a bastion of affluence. In 1960, Hartsdale was a small, unincorporated area located within the township of Greenburgh, which had a population of around 76,000. Hartsdale covered about eight square miles when Ann and her daughters lived there. Historically, Greenburgh was predominantly Black. Many laborers had moved there during WWI, and, after WWII, middle-class Black families and large Jewish and Italian populations settled in the area. Though white middle-class households had become the majority in Hartsdale by the time Carolyn was of school age, the Greenburgh township was still fairly diverse, particularly in comparison to the rest of surrounding Westchester County.
In 1968, when Carolyn was two, Hartsdale witnessed an extremely contentious school-district merger, including the Bessette sisters’ future school, Juniper Hill. The New York Times reported that some Hartsdale parents opposed on the grounds that it would compromise their children’s education by mixing them with “slower children,” apparently motivated by racial bias. Yet others lobbied on its behalf, wrote letters, and went to Albany and “pounded on the Commissioner’s door.” In August of 1968, the Hartsdale and Greenburgh school districts were merged and desegregated, resulting in a student body that was 75 percent white and 25 percent Black.
After the Bessettes moved to White Plains, Carolyn and her sisters remained at Juniper Hill School, indicating that Ann supported the merger and wanted a diverse environment for her girls. Ann sometimes taught as a substitute teacher at the school and was therefore a colleague of Carolyn’s third-grade teacher, Mary Lou Darkenwald. Mrs. Darkenwald remembered Carolyn as “a very bright, confident, attractive child. She was outgoing but in a quiet way. Juniper School now had a diverse, integrated student population. Carolyn fit in nicely. She wasn’t at all prissy.”
Carolyn’s criteria for friendship were kindness and humor. You had to be able to laugh, and even better if you could make her laugh. Yuma loved Carolyn’s bubbling, infectious laugh so much that she was willing to risk getting in trouble to hear it. “I was sitting next to her, our desks side by side. I remember wanting to make her laugh all the time because it was so fun, so nice to hear that distinct laugh,” she said. “So I did an impression of another kid who had complained that the classroom floor was dirty. Carolyn’s giggle bubbled up and out into a belly laugh. I’d do whatever I could to hear that.”
Carolyn and her classmate Jodi Savitch adored Mrs. Darkenwald, who conducted her classroom with a light touch, quieting the children with the French phrase “Fermez la bouche!” The kids thought this was very funny, but they obeyed. Carolyn and her friends braided each other’s hair while Mrs. Darkenwald read to them from The Lion, the Witch and the Wardrobe by C. S. Lewis
“Every day did feel like it meant more,” recalled Jodi. “The whole world was a wondrous surprise then. Carolyn was alive to it all, basking in words, transporting her mind through books and newfound equations, hopping on rocks, scrambling up hills, and exploring harbors. Behind Carolyn’s house was a stream, and she had these many wonderful rubber animals that were a mainstay of our play—she loved animals. We made up our own magical kingdom and took turns naming our flock. I lived just up the street, and we would play like this for days. We were underwater explorers; we were horse trainers; we were on a jungle safari.”
In fifth grade, just before moving to Greenwich, Carolyn met Howard Brodsky in her class at Richard J. Bailey School in White Plains, where she had gone after finishing third grade at Juniper. “She was so kind,” Howard remembered. “My mom had died the year before, and not all the kids were considerate. Some were worse than inconsiderate and said things like, ‘Ewww, you don’t have a mom?’ Kids will be kids, I suppose. But not Carolyn. When she heard that, she took me aside and put her arm around me. ‘Don’t listen to them. Just ignore them. They don’t know what they’re talking about.’ ” Howard developed a crush. “I lived further away and would walk the forty-five minutes to her house every chance I had, just to see if she would come out.”
“What struck me most about Carolyn,” remembered Jane Youdelman, “was that she was always full of hope. It’s an undervalued characteristic. But she moved through the world brimming with a countenance that exuded ‘What fun thing will I get to do or see today?’ It made everything around her that much more enchanting. And it wasn’t just because she was a child. It was a trait she held on to for a very long time.”
The Bessette home was always the place to be, with Ann happy to have other children over. “It was a lovely house, and Carolyn always lit up a room,” Jodi said. “She was so very sweet. Always. I remember her sisters smiling at us and helping us with snacks. Carolyn would make the most unusual flavor creations and insist I try them, too. One day we had cheese and crackers, and she held one aloft, adding a sprinkling of McCormick’s lemon and pepper seasoning on top, one of her stranger concoctions. Or at least I thought it was strange until I tried it. It was too good.”
Like Jane and Yuma, Jodi was devastated that her friends—not just Carolyn, but also Lauren and Lisa—and their warm, welcoming mom were moving away. And like Jane and Yuma, she does not remember ever meeting Mr. Bessette.
“Carolyn’s mother came in for regular teacher-parent conferences,” recalled Mrs. Darkenwald. “Her greatest concern was that Carolyn wouldn’t be adversely affected by the divorce, that she didn’t experience issues or problems because of it.”
Mrs. Darkenwald allayed Ann’s concerns about Carolyn. “She was the kind of child you wanted in your class,” she explained. “Once you provided her with a framework for a particular subject—reading, writing, or math—she took off on her own. Carolyn was never a problem child. She was well-behaved, polite, and well-brought-up. She was active and had a number of girlfriends in class.”
As continued to be the norm, her father was an outlying presence. “I don’t know what role Mr. Bessette played in Carolyn’s upbringing,” Darkenwald said. “He evidently paid maintenance and child support for his three daughters. I think he saw them from time to time.”
THE OFT-TOUTED MEDIA ASSUMPTION that Carolyn was a product of WASP privilege is laughable in light of the facts of her upbringing—Carolyn was raised in a predominantly Italian American household. Her maternal grandfather, Carl Calopero Messina, was born December 6, 1907, in Castellammare del Golfo, in the province of Trapani in Sicily. He emigrated to the United States in 1917, and by 1930 lived in Brooklyn with his younger brother, Giovanni, and his mother, Anna, while his father, Gioachino, stayed behind in Sicily. Tall with blue eyes, Carl married Jennie Venturalla, a beauty full of mirth and mischief, and the couple made their home near his mother on Bay 40th Street in Brooklyn. Jennie’s father, Dominick, had emigrated from Italy at the turn of the century, so while she sounded American, Carl’s Italian accent was strong.
Their daughter, Ann Marie Messina, was born on August 5, 1939, and her younger brother, Jack, arrived four years later. Carl was a screen printing and textiles foreman at Blum Screen Print Works, where he earned a salary of $1,600 per year while Jennie raised the children. In the mid-fifties, the Messinas moved to Ossining, another mecca of Italian immigrants in the postwar years. Carl and Jennie found employment at Printex, designer Vera Neumann’s silkscreen-printing business housed in an 1810 Georgian mansion with views of the Hudson River. Carl was again a foreman, while Jennie was a sample maker for Vera’s iconic scarves, which she began making with parachute silk after linen became scarce during WWII. Neumann’s scarves—featured in a 2010 Smithsonian Museum retrospective—were as bold and bright as Lilly Pulitzer’s, but with a New England, seasonal palette. While Vera may have been the designer, the Messinas were the artisans, their work a point of pride in the family.
To be an Italian American during the early 1900s was to be subject to appalling bigotry. A wave of nativist hostility engulfed the country during the Great Depression. Pseudoscientific racist theories claimed that “Mediterranean” types were criminal, even subhuman. From the twenties until the late sixties, Congress curtailed Italian immigration (along with restrictions on a broader range of nationalities) on racial grounds. Some prejudice subsided once immigration slowed, but tensions rose again during WWII. While the internment of Japanese Americans is well known, the US government also relocated ten thousand Italian Americans away from coastal zones to military camps throughout the United States and restricted the movements of six hundred thousand more. If Carl were to speak of Italy, where his father still lived, he could be tried for treason.
The epithets “dago” and “wop” were commonly used, even after Italian Americans had proved their loyalty to the US by their presence in the WWII armed forces. Carl signed his draft card in 1940, a year after his daughter, Ann, was born.
By 1983, the New York Times headlined an article with “Italian Americans Coming Into Their Own,” but it had been a long and painful journey to social acceptance in white Anglo-Saxon America, and prejudice lingered. Carolyn grew up in a decade when, even more so than today, non-WASPs were considered socially subordinate—a far cry from the virulent racism that Blacks and others have long experienced in this country, yet a pertinent facet of the American sociocultural landscape.
Ann attended Ossining High School and participated in the Spanish Club throughout her years there. As a senior, in 1957, she was Classes Editor of the school yearbook, Wizard, and voted Best Looking by her classmates. Like Carolyn, her beauty was unconventional for her time, more Roman, with hints of Linda Evangelista and all the more riveting for it. Under the heading “Prophesies,” where seniors made predictions for one another’s future, Ann Marie was seen as “The Pepsodent girl with the million-dollar smile.” All the seniors were pictured with their chosen pastime and ambition beneath their face. Ann Marie Messina’s senior photo listed her pastime as “Playing ‘hard to get,’ ” and her ambition as “Teacher.” Carolyn would inherit all of these traits from her pretty, intelligent mother.
William Bessette, Ann’s future husband, graduated from Crosby High School in Waterbury, Connecticut, two years earlier, in 1955. His yearbook photo shows a handsome young man whose smile suggests he knows it. Underneath the dashing photo is the caption, “Adept at all sports, Bill’s A-1 swimming skill has made him a top-notch Red Cross Senior Life Saver. Next to swimming, basketball, and bowling, girls are foremost on his list of interests. An alumnus of Middlebury’s Shepardson School, Bill will enter the University of Connecticut.”
Ann enrolled at the University of Connecticut in fall 1957, and there met the good-looking junior William J. Bessette, who was majoring in civil engineering. William, older brother to Thomas, Dorothy, and Diane, was a member of the honor fraternity Chi Epsilon for civil engineering students and the American Society of Civil Engineers, which promoted professional contacts. William was also a member of the Newman Club, which was a Catholic student organization. And he is listed as Social Chairman, though of what we are left to guess, but his busy calendar anticipates his youngest daughter’s gifts in the art of friendship.
True to her declaration in the Ossining High School yearbook, Ann was working toward becoming a teacher, determined and driven like her parents. She studied Elementary Education, becoming a member of Kappa Alpha Theta, and was again on the staff of the yearbook, The Nutmeg, where she helped write the Year in Review.
Carolyn’s uncle Thomas Bessette recalled his older brother bringing their mother and him to meet Ann’s parents, Jennie and Carl Messina, in Ossining: “I was quite young, but I was impressed by the fact that if you looked out their living room window, the prison was right there. Sing Sing in your backyard. Ann was beautiful; I loved her parents.”
The Nutmeg of 1961, Ann’s senior year, had a page covering the 1960 presidential race between JFK and Nixon, complete with photographs of each candidate. JFK’s face—handsome, though with somewhat mournful eyes, and framed by his full head of hair—and Nixon’s face, with its used-car-dealer smile, exist just a few pages away from Ann Messina’s face. While flipping back and forth between the parents of Carolyn and John, one can’t help but see the features the father passed down to his son and the mother passed down to her daughter.
Ann graduated with her bachelor of science in education in 1961. Though two years older, William, who worked throughout college, graduated in 1961 with a bachelor of science in civil engineering.
A year later they were engaged to be married. An announcement appeared in the August 30, 1962, issue of the Reporter Dispatch of White Plains. The headline read, “Miss Messina, Teacher, to Wed in Fall.” Yet the article reported, “A Spring wedding is planned.” In fact, their wedding took place the following summer, as that fall a tragedy occurred in the Bessette family.
William’s father, Alfred Bessette, was a foreman for the Connecticut Light and Power Company. On October 11 of 1962, he was conducting a routine inspection of power lines in Middlebury, Connecticut, when he was electrocuted by 115,000 volts of electricity. He fell more than twelve feet from his ladder to the ground, sustaining burns on his face, neck, both arms, and lower body, and spent six weeks in the hospital “languishing in pain,” as a family member put it. (While this private grief played out, President Kennedy, on October 22, alerted his citizens to the Cuban Missile Crisis, which sent a wave of shock and panic through the country.) Alfred died on November 9, 1962, at the age of fifty-eight, leaving his wife, Anna, a widow at fifty-three. William was twenty-six years old. His younger brother, Thomas, was sixteen.
Ann and William married on June 29, 1963. They were both two years out of college, during which time Ann worked as a school administrator and substitute teacher at Douglas G. Grafflin School in Chappaqua, New York. William was working toward his New York State certification as a civil engineer.
Then, on November 5, 1964, Ann gave birth to twins Lauren and Lisa. Carolyn arrived just over a year later, in January 1966.
William experienced these major life events in the aftermath of his father’s sudden death. Early parenthood is a time when you want your own parents to be there, if only to ask, “Am I doing this right?” But also, hopefully, to lend a hand—especially if you have twins.
At this time, Ann’s mother, Jennie, became increasingly concerned about her daughter’s marriage, and about her son-in-law in particular. Ann, she felt, had been left to care for three toddlers by herself even as she had to continue working. According to Roseann Flood, Jennie’s colleague at Vera Neumann, “Ann and Jennie were very close. All Jennie spoke about was her worry for Ann because there were problems with William. Ann wasn’t happy. Understandably.”
As with college, William’s engineering certification was prolonged. New York State requires four years of work in the field and one six-hour exam, which would have put William as earning his license in 1965. Carolyn would, years later, refer to this period as one in which her father “needed to continue his studies to be further certified.” But she said, “Apparently it wasn’t happening.”
Acquiring the license took William until March of 1967, a year after Carolyn’s birth. He went on to have a long career at Turner Construction International, where he worked on large public projects with a specialty in airports. William was a meticulous man who was, according to family members, “very, very anal-retentive,” and his work took him to Las Vegas, Qatar, and Egypt. It often required long stays on-site, often for months at a time. On May 25, 1974, Ann filed for divorce from William in Westchester County Court, when Carolyn was eight years old.
ANN AND HER CHILDREN faced many difficult transitions over the course of their lives, but none so stark as becoming a single-parent household. “Eventually,” said Roseann Flood, “Ann moved with her three toddlers to Jennie and Carl’s for a while, who helped her with the girls when Ann was at work.” Perhaps this is why Carolyn began kindergarten earlier than most children, at four and a half years old, rather than at five.
The split put the family under stress within and without—at home, the children had to make do with one parent around for day-to-day activities, and in the outside world, despite semi-liberated seventies proclamations of single mothers as superwomen, they were sometimes eyed with suspicion for breaching the norm. It was not just the mothers who felt the judgment—their children did, too.
Ann and the children moved back to Old Knollwood Road after William vacated the house in favor of an apartment elsewhere in White Plains. Carolyn intermittently asked her mother why they divorced but could never wholly wrap her head around it. William’s absences would form Carolyn’s experience of her father after her parents’ divorce. “When we went out, just the two of us, she would talk about being hurt that her father was not around,” said her friend MJ Bettenhausen. “She still wondered about all the memories, as she was so young when it happened.”
Despite having little memory of her father in the house, on rare occasions, traces of her feelings toward him surfaced. She once explained to a colleague who had asked her why she always ate so quickly. “I got in the habit as a little kid,” Carolyn replied. “I couldn’t stand the tension surrounding my father, and the sooner I finished dinner, the sooner I could get away.”
Carolyn’s emotional and psychological makeup was also significantly influenced by her maternal family and had much to do with her unwavering curiosity, drive, and insistence on authenticity—they had an aversion to pretense. A nimble strain of humor ran in the Messina family, as evidenced by Jennie’s frequent ripostes. Once asked if she was afraid to live so close to Sing Sing prison, Jennie shot back, “Sweetheart, trust me, if someone breaks out of jail in Ossining, the last thing they’re going to do is stay in Ossining!”
Jennie had demonstrated the value of community responsibility by example: She volunteered at Phelps Memorial Hospital Auxiliary. Ann herself was always active in charity work with the Boys & Girls Clubs of America and Kids in Crisis. She imparted this caring spirit to her daughters, who participated in the Camp Fire Girls, the first co-ed, nonreligious, and multicultural organization for girls in the US; its playgroup counterpart for younger ones, the Bluebirds; and the three sisters sang to the elderly in retirement homes.
Throughout Carolyn’s childhood, Ann’s steady presence was the defining feature. Teaching her girls to make their own way and cultivate a solid work ethic was of the utmost importance to Ann, who had been raised among strong women with confidence, self-respect, and ambition as inherited traits. A friend of Carolyn’s remembered Ann’s sense of humor: “She laughed as much as Carolyn but suffered no fools.”
Fortunately for the Bessette girls and their mother, a new father figure was about to come onto the scene. According to a friend, when Carolyn needed treatment for scoliosis at nine years old, Ann brought her to the acclaimed orthopedic surgeon Dr. Richard G. Freeman. Dr. Freeman was a recent widower; his wife, Marion, had died in 1975. He had three daughters of his own, Kathy, Diana, and Lori, and according to friends was an openhearted and nurturing parent.
Dr. Freeman was calm and funny—a distinct change from intense William. Ann and Richard fell in love and were married in 1977. A few months later, “at my last conference with Carolyn’s mother,” recalled Darkenwald, “she informed me that they were resettling in Greenwich.”
By January 27, 1977, when William bought Ann’s share of the Knollwood Road house, Ann was no longer Ann Bessette; she was Ann Freeman. In Greenwich, the Bessette women joined the large Freeman household on Lake Avenue, a street of rolling lawns and stately homes. Although Ann’s situation improved after marrying and moving to Greenwich (among other things, Freeman would turn out to be a loving stepfather), she never forgot where she came from—and nor did her youngest daughter. Carolyn’s beginnings—in which her Italian American mother found herself single and raising her children alone after her husband’s departure—would reverberate throughout her life.