Although girls were not allowed to go away on weekends until senior year, when Theodate Pope Riddle invited her younger twin cousins for a weekend at Hill-Stead, Miss Hillard let them go, explaining that she was granting the favor to Mrs. Riddle, not to the girls. In another case, when Margaret Bush was a new girl and asked her headmistress if she could change roommates, she replied, “Margaret, I have never made a mistake in the kind of a girl I’ve admitted to Westover, but I see that I have made one in you.” Margaret felt crushed, but when the term was over Miss Hillard changed her mind and let her do it. (She declined.) The young woman turned out to be a leader who was elected president of the senior class, but in her opinion she and her sister were given special privileges only because their headmistress was so fond of their father. “Not everyone liked Miss Hillard because she had favorites,” admitted another student. “I liked her because I was one of her favorites.”
Although Mary Hillard knew that it was often difficult “for a girl to leave home and learn to stand on her feet,” as she put it to her sister Emily, she was not always sympathetic toward homesickness. “The shock and surprise and excitement of it often make a young girl really ill even though she may be really enjoying it,” she theorized. This attitude is evident in the case of Jeannette Rich, who spent most of her first months at Westover in the infirmary suffering from psychosomatic aliments caused by extreme homesickness. One day when she saw Miss Hillard in the hallway on her way to New York, she timidly asked if she could go home a few days early for Christmas vacation. The headmistress snapped at the girl that she could go home and stay home because she was physically, mentally, and morally weak. The girl burst into tears and rushed off to find Helen LaMonte, who comforted her throughout the rest of the day, until Miss Hillard telephoned and softened her harsh words. Later that year, when Jeannette was in the infirmary with a sports injury, the headmistress stopped in to see her, remarking that she was glad for the accident because it gave the girl a chance “to exercise fortitude.” Although shocked by her words at the time, Jeannette never forgot them and afterward even found them helpful.
While Miss Hillard’s discipline was often erratic, either too strict or too permissive, it was sometimes relieved by her sense of humor. In the late 1920s, she used to board the bus of girls going to Taft for a tea dance to make sure no one was wearing lipstick or rouge. Once when she ordered a pink-cheeked blonde to rub the rouge off her face, the petrified girl denied that she that she was wearing any. The headmistress, the girl remembered, “stared at me for a breathless second, and then with that twinkle that occasionally appeared, she said, ‘My dear, I congratulate you.’” Another time when a student took a dare to sleep in the headmistress’s bed when she was away and was discovered upon her early return, Miss Hillard was again amused.
Her way with girls, however, did not work as well with boys, at least with her nephew, Archibald MacLeish, a son of her sister Martha. When, at Mary’s urging, Archie was sent from his home near Chicago to Hotchkiss School, a boys’ preparatory school about forty miles from Middlebury, she became as close to him as she had been to her deceased younger brother John. “I have a new young nephew come East to school,” she wrote happily to a friend. “He spent Sunday with me and kept me inwardly smiling [because] he was so dear and unconscious and so funny.” That autumn her youngest nephews were christened in Westover’s chapel with Archie and a cousin acting as godfathers and Aunt Mary as godmother. The moving service, attended by relatives, friends, students, and staff (including the handyman, maids from the West Indies, and laundresses from Ireland), made her weep. A few weeks later she described the “chapel full of those lovely girls with their angelic reverent young voices chanting the hymns,” an experience that “makes one’s heart rise up to one’s throat.” After the christening, a few girls were invited to join the older boys in the headmistress’s sitting room, where she read Romanian and Irish folk stories aloud until the bedtime bell.
One spring evening when Archie was eating at the head table on a raised platform in the dining room, a senior asked the very pretty Ada Hitchcock to fill an empty seat. Eighteen-year-old Archie was immediately infatuated with Ada, but, after learning that he was writing her every day, his aunt tried to discourage the match. She thought he was too young to be in love, but there is another less benign interpretation. Ada was the daughter of a self-made merchant in Farmington, and Mary, according to family lore, wanted her nephew to marry a girl from a more prominent family, like Esther Cleveland, the daughter of a former President. The MacLeishes welcomed Ada warmly, however, and the pair planned to eventually marry after Archie’s graduation from Yale, where he was class poet. After his stint in the army and enrollment in Harvard Law School, a wedding date was set in June of 1916. Aunt Mary slowly came around, but in such a dominating way that Archie half resented her giving a dance for them, taking over the wedding rehearsal, and putting them up at Crossways the night before their honeymoon in Bermuda. (His sister, Ishbel, graduated from Westover that spring as president of her class and winner of the John H. Whittemore award for “Faithfulness, Justice, Truth, Humility,” then followed in her mother’s footsteps to Vassar.)
Miss Hillard thought her nephew would make a brilliant lawyer, perhaps fulfilling the promise of her beloved brother John, so she also opposed Archie’s growing interest in becoming a poet. When he turned down a partnership in a Boston law firm to move to Paris and write poetry, she furiously tried to talk him out of what she regarded as a bohemian way of life. During a bitter argument, she called him a Bolshevik and he responded by calling her a reactionary. Since she had always adored poetry and had introduced him to John Masefield, whom he regarded as the greatest living English poet, Aunt Mary was in a precarious position. “I do not think even she would argue that the law as a career is more desirable than letters,” Archie wrote to his mother. Again his parents backed him, and the young couple and their child moved to Paris.
It was one of the times when Mary Hillard was wrong about what was right for a young person. Many years later the Rev. John Dallas wrote about her tendency to be willful and wrongheaded. “There was a majesty and almost a fury in her love,” he observed. She “never knew or understood how she wounded,” but afterward would try “to put together again what she felt she had broken.” And, he went on, what often looked like possessiveness was her ability to see another’s potential. “It was not to superimpose her own will upon another that made her love seem a fury. Rather it was a desire deep within her intelligence and will … to compel the recognition of the vision which consumed her soul … Fire burns. The result often hurts.” Mary was well aware of this character flaw. “I too give pain without knowing I do when if I could exercise more imagination and restraint I would not do so for anything,” she admitted to her friend Harris Whittemore. In retrospect, it appears that much of the advice she gave her girls over the years was learned from her own excruciating experiences.
MacLeish’s anger deepened after his aunt wrote him in France that she disliked his poetry and so did the editors she showed it to. After she refused to read a published book of his poetry, Archie wrote his mother that “I have definitely, and, I am afraid, not very regretfully, broken with Aunt Mary.” He asked his aunt to stop writing and trying to see him. Nonetheless, his feelings remained ambivalent and while still abroad the couple named their newborn daughter Mary Hillard MacLeish. When they returned to the United States, Archie made a tenuous peace with his aunt, but his anger lingered. When she asked him to read his poetry at Westover the year before her unexpected death, he refused. After winning the Pulitzer Prize for poetry in 1933 a year later, he did give a reading at the school, and Ada gave a performance of French songs she had learned in Paris. He returned to Westover again a decade later when his daughter was unhappily enrolled, when he gave a dramatic and disturbing talk about his youthful falling out with the woman he later called his “intelligent and experienced and lovely” aunt. It gave him a feeling of release, but he still did not understand her devastating opposition to him as a young poet.
As a result of her love of poetry and the other arts, Mary Hillard also believed that a balanced life was a cultured life. Over the years,