Chapter 3 - I
I know a lot of women had a crush an him... "I know a lot of women had a crush an him, I mean 1 was just like gaga for about a year and a half or something like that. He was a very sexual person. I mean the way he looked down at some of the girls -- it would just send them. And the other part of his personality, particularly early on, was that he was what people felt was vague, Therefore when kids got to the school, they used David for whatever figure they needed to relate to. He could become the stern father, he could be the inspiring older brother, he could be the loving, forgiving father to the Queen's taste -- for lots of the girls that was true, and some of the boys -- he could be a tremendous rival, any image that needed to be filled out for those kids. He could be any kind of father that the kids wanted, particularly because he only acted it out right there in the middle of the Common Room. He never acted things out in a way that upset those fantasies in a destructive way." -- Buffy Dunker, [interview, pp 83-84]
By the time Ken Webb had fully dissociated himself from the school in June 1948, the Woodstock Country School had long since become David Bailey's school -- emotionally, philosophically, and in mundane daily practice. Ken's departure merely made reality official, the same encroaching reality that Ken had acknowledged to himself during the very first term of the school. Since both Ken and David were determined that Woodstock should be student-centered and democratic, it was all but inevitable that David would emerge as the school's dominant personality, the benign and sometimes enigmatic dictator who defined the school's essential character.
Ken was never fully comfortable with adolescents Of all the factors that contributed to Ken's leaving and David's staying, probably none was more important than the way they related to students. Ken was never fully comfortable with adolescents, he was not terribly sympathetic to adolescent problems, and he tended to prefer absolute solutions universally applied, rather than adopting a childby-child approach that was or seemed inconsistent. He worried in his diary about his relationships with students, but he was never able to resolve the problem satisfactorily, even for himself. While he certainly had friends among the students and was widely respected as a teacher, he was also a figure of fun, the butt of jokes. No headmaster, least of all a co-director with a built-in rival, can last long in such an atmosphere as other heads of the Country School would learn in later years. Little wonder, then, that Ken was drawn increasingly to his camps in Plymouth, not merely because they ran only in the summer, nor because they were dedicated to play -- serious play oftentimes, but play nonetheless -- but most of all because they were populated by younger children, most of them pre-adolescent.
David, on the other hand, liked adolescent young people. David, on the other hand, liked adolescent young people. He enjoyed their company, their struggles, their freshness, their difficulty. He revelled in the challenge ofgetting a troubled child to turn out all right, and he especially liked to think the school could do better with most kids than their parents could. For all that he played games with the students -- sports, parlor games, bridge and chess, as well as more complex mind games -- he was never trying to be one of them. He always maintained a certain distance as 'the adult, the authority-figure, the headmaster, no matter how teasing and silly his behavior might get. For many, perhaps most Country School students, David's character, with all its contradictions, surprises, inconsistencies, was a vital, pleasant, or at worst neutral center for a school experience which was more exciting and varied than most students had even thought possible. People who knew Woodstock in its best periods over 30 years commonly use words like "paradise" or "magic" to describe the experience. (Even Peggy Bailey, David's wife, who sometimes considered David's flexibility in his dealings with the children too lenient, nevertheless acknowledged that "with all his faults -- God knows we all have faults -- David had this kind of magic touch with the young," which eluded her description and remained essentially mystical.) [Peggy interview 6/16]
"David had a genius for understanding adolescents," recalls Gerry Freund, who came to Woodstock as a student in 1943, and remained close to the school for the rest of its life, serving as a trustee for most of those years. "David was not an adolescent, except that he had something of the spirit of an adolescent. He was was able to be an adult who could cool into adolescence. He played his role by playing chess in the common room and drawing people out over different moves. He played his role by being out on the soccer field, encouraging a girl who needed to wear off an enormous energy to compete just as heavily in soccer -- I think of one girl in particular, the daughter of a professor at the time, but there were many others. He blew the whistle on people, kind of literally, and figuratively who needed to have the whistle blown on them. Of course he made mistakes, here as with other things. But he was regarded by all of us as fundamentally well-intentioned and, in that sense, fundamentally fair. He was always pretty remarkably conservative, although for his time, remarkably radical."
He and his brother and two sisters grew up in a big house on Boston's Beacon Hill. David Bailey came by his contradictions honestly, from a mixed background of the restraints of old money and the provocative curiosity of visceral rebelliousness. He and his brother and two sisters grew up in a big house on Boston's Beacon Hill. His father came from an old Boston family, had gone to Harvard and Harvard Medical School, and he was a doctor, a chest specialist. David's father had rather traditional expectations of his children, especially that the boys should go to Harvard, which they did (as did David's son Peter years later). But neither of the Bailey boys accepted these traditional expectations easily. David dropped out of Harvard and floundered about for several years until he found himself in the first student body at Black Mountain College. Although his younger brother Tad graduated from Harvard, he went on to art school and a lifelong career as an artist and social activist, very much at odds with mainstream American culture, but very mannerly in his opposition.
Ruth Perkins Bailey, was a New Yorker whose natural style was already a bit much for her Bostonian circle. David's mother, Ruth Perkins Bailey, was a New Yorker whose natural style was already a bit much for her Bostonian circle. Even though she, too, came from an old monied family, had a father who had fought in the Civil War, and had been educated at an exclusive girls school, she was also an independent woman for her time. David's wife Peggy remembers her mother-in-law fondly: "She was an aristocrat and was used to having servants and money all her life. She was of an aristocratic family, but also an aristocratic inside, you know, as well. She didn't go on to college, she did the traditional trips in Europe with her mother, who was a very wealthy woman, and there she intensified her love of the beautiful and her taste for exquisite furniture and paintings and all this kind of thing which she collected greatly. She was also physically very brave, much braver than I. Once, as a young woman, when she was alone in one of the great houses that she lived in, a burglar came in and she chased him downstairs and out of the house."
From his mother, David got his independence, his love of the arts, his sociability, even his sense of humor. But his father was a taciturn man, always beautifully groomed, very courteous, with great charm -- but he rarely spoke. And he spoke even less during his long, ligering illness during David's adolescence and young manhood. Little wonder, then, that David's personal style should have been so oblique, relying as it did so much on sly humor, implication, nonverbal responsiveness, and often leaving the most important things unsaid.
Ruth Bailey was devoted to her husband, she took wonderful care of him at their home in Barnard, and after he died there in 1938 (?), she stayed on in Vermont. She took an active interest in local affairs, made friends with Elizabeth Johnson, and cheerfully contributed her decorating talents, and much of her art and furniture, to making Greenhithe elegant for the opening of the Country School. "She had a wonderful sense of humor," Peggy Bailey recalls. "Tad and David would both tease her, and she was always good humored about it. Oh she had, like all of us, she had faults. One of them of course was this extraordinary generosity which verged on extravagance. She was always giving things to people, incredible number of things. Not just to relatives, but to friends, and not so good friends, but she was just like that." [Peggy Int IV, pp 12-15]

David's education largely reinforced his independent character, particularly his years at the Shady Hill School in Cambridge. Years later at Woodstock, he would often draw on ideas and experiences from Shady Hill, adapting them to his Woodstock circumstances.

He also went to a progressive, coeducational, vegetarian, pacifist boarding school in Switzerland when he was 16 and his father was one of Herbert Hoover's dollar-ayear men trying to help Europe recover from World War 1. His brother and sisters went with him to the Swiss school, about which he recalled none too fondly, "The school was run by a Swiss pacifist -- he used to go to jail every year instead of serving his military term. My siblings and I were the only Americans in the school. We used to walk +our miles to get the school milk. We used to eat dried flowers. It was a vegetarian school." [CONT. III/4 p.4] One of the reasons David was sent to that school was the hope that the rugged mountain regimen would help his tubercular condition, which did in fact clear up. For the rest of his life he remained vulnerable to heavy colds, pneumonia, pleurisy -- and finally the emphysema that cut short his career and his life. [Peggy Int 9.82, p.6] David's increasing disenchantment with his educational experiences culminated at Harvard, where he did not do well and dropped out after two years, largely out of disinterest. About the only positive part of his time at Harvard was studying Shakespeare with Ketteridge. Otherwise, he was not getting what he wanted or needed. At the same time, his health was somewhat frail, so that in 1933, when John Rice was recruiting students for his experimental Black Mountain College in North Carolina, that sounded good to David as a fresh learning experience, and it sounded good to his father to get David into the high and dry mountain climate where his health might improve. There, as it turned out, he would also meet his wife.