Dark-haired with a long nose and a penetrating look, she had very definite opinions. It was said that she had once marched down Fifth Avenue in a suffragette parade. She seemed to embody the highest ethics, indicating a slight air of scorn for what she regarded as inferior. Outspoken in a quiet way, she told girls, “when in doubt—don’t,” and urged them to be unafraid. With her twinkling eyes and wry smile, she drew to her those who were homesick, needed advice, or wanted permissions. She allowed a girl to use her office for a visit with a beau when the visiting rooms were taken, and at another time let her go to a Yale football game with him without a chaperone because his father was a well-known minister. “We opened our hearts to Miss LaMonte and adored to be near her. We could tell her our secrets and little problems, and she would always make us feel comfortable and happy. She radiated warmth and understanding and would always greet us with a smile and a word that made us feel adequate and at ease. She gave us a feeling of security and of being worthwhile,” recalled an early graduate. “And most of the time we were her heroines,” remembered Betty Choate Spykman. Miss LaMonte never thought girls did anything wrong, “and if we had a real success, whatever it might be, she rolled her eyes and clasped her hands in rapture.”
After her school had opened, Mary Hillard took more time for her private life. In fact, it was necessary for her to withdraw from time to time. It was on a Sunday in August of 1907 that she first met New York art connoisseur Augustus Jaccaci at Hill-Stead, when he was working on a book about private art collections. Mary described him in a letter to her sister, Emily, as “an Italian of aristocratic birth … very cosmopolitan, very brilliant, and with a rare simplicity and sweetness of nature which makes him one of the most delightful companions.” She soon asked him to make five hundred editions of Westover’s first catalog with gilt edges and a silk-lined slip jacket. She and the darkly handsome European she came to call “Jac” became dear friends. After he returned from a trip to Europe, she wrote him that “New York is a better place when you are in it,” and she sent him a share of stock in the Westover Corporation as thanks for his work. On her visits to New York during 1909 and 1910, they often dined and went to the theater together. “Our beloved (though sometimes misguided) principal returned from New York Saturday morning in excellent health and spirits,” observed Lucy Pratt. “She had been to concerts to her heart’s content by night and by day she had done more things than my pen knows how to write.”
Mary Hillard’s more than thirty surviving letters to Jaccaci have all the warmth, informality, and intimacy as those to her closest relatives and friends. “Dear Jac, you were such a deep comfort to me last night,” she wrote in one of them, saying how much she needed his friendship. Their closeness is indicated by her revelation of an important secret to him. “It was wonderful I could tell you what I did last night. You would know it is something I can hardly speak of—never do speak of—but I wanted to tell you Jac. For I want everything that makes you and me closer to each other. We each can help the other, we both need help. We are both generous, and generous people have especially human sympathy and affection, for they give out so much. Dear Jac, I’m so grateful to you, and I’m so grateful for what you were and meant to me last night.”
In the summer of 1910 she wrote to him in the most intimate manner, revealing that she enjoyed his manliness and felt he appreciated her womanliness. Writing from a vacation cottage in the woods, she alluded to the demands of what she called her “big ‘job,’” and asked him to imagine “what, under those circumstances, the brilliancy and cultivation of your mental powers is to me—the joy of having that in a companionship!” After he referred to her as “Mother Mary,” she rhapsodized that “you read my heart.” She went on: “You need me and I am here, and motherliness is measureless. You may be what you will—glad, grave, weary, troubled—It is all the same. It makes no dif-ference to the great deep understanding that knows you and cares. No one else could understand. But we do. We are both so simple. We both need companionship, comfort, healing, in this pathway of life which is so hard for each … you need the tenderness and the cherishing that wells in a woman’s heart. And I need the strength and courage that lives in high manhood.”
A few months later, in early January of 1911, when the man she had called her truest of friends suggested bringing visitors to Westover on a Sunday, she charmingly turned him away. “What a nice party you suggest! And how inhospitable not to say ‘Do come.’ But—dear Jac—the work we have to do here is something tremendous. It calls for all one’s wisdom to know how strength and vitality and powers of the mind can be so safeguarded as to be equal to the demands of schoolwork—and be fresh for it, and full of the joy of working. (My new secretary says, ‘I am so enjoying working here. This is such a happy place. Everyone is so happy. I love the work here.’) I have seen clearly that our hope lies in our quiet winters. Spring and Fall our friends come in great companies. We love to have them; we welcome them. Our safety lies in absolutely quiet Sundays, and in this blessedly quiet winter term. I have no right ever to go against my judgement in these things. You understand fully. So tempting as your attractive party is I know I am doing my bounden duty to Westover in asking you to wait over the Spring term. I shall love to have you all come up some day in May [if] you care to.”
She continued: “And as guests must be at times excluded from the home, so that these beautiful, living vital influences of the home may have freedom to gather and express themselves, just as flame springs from the log, and transforms the grey cold fireplace into a source of light and warmth, so the same conditions must be maintained in the life of such a kind of school as this is, that here may be that mysterious warmth and light and intimacy that comes in separation from the outer world, when the vitality within us, not taxed with social demands, may turn to the intimate daily life and the joy of that fellowship. That is what this beautiful snowbound winter term is to us. We protect it. Should we not? Even if it sometimes, as now, [it] becomes suddenly difficult to do so because one would rather not?”
After so firmly putting the mood of her beloved school above their relationship, either her letters to him ended or he no longer saved them. She continued to turn to him at times, to make memorial books for John Whittemore and Alfred Pope, for instance. After war broke out in Europe, Jaccaci returned to Paris, where he helped French and Flemish refugees. In the winter of 1915 he wrote to her with thanks for getting “the whole of Westover” involved in his cause, for which the King of Belgium later honored him. After the armistice he returned to Middlebury one more time, in 1919, when he signed the handsome leather-and-gilt school guest register he had designed many years before.
Mary had confided to “dear Jac” about her difficulties with Theodate, a member of the school’s board of trustees, who, she wrote, seemed “troubled and tremulous at the slightest suggestion of anything connected with Westover.” After the school had opened, tensions had arisen between the two strong-willed women. “Genius, and she has it, needs the kind of love somewhere that childhood needs. I give it to Theo very imperfectly because I think of myself too much (partly because the demands of daily life attack one so fiercely),” Mary wrote to him after Theo had sailed to Europe without saying goodbye. Photographs of Westover were included in an exhibit of the Architectural League of New York in 1910, and Cass Gilbert, president of the American Institute of Architects, later praised the structure as more “beautifully” designed than any girls’ school in the country. The two came up with the idea of giving her a gold medal inscribed “Theodate Pope, architect, 1910” in a leather case to help “dissolve that intangible something—we do not know what—that has seemed to send a frost through her thoughts of me.” (Theodate would finally be elected to the American Institute of Architects in 1918 and licensed to practice architecture in Connecticut in 1933.)
Problems had arisen between the two friends, because Theodate Pope would unexpectedly descend on Middlebury with a group of people to show them “her” school and receive a cool reception from Mary, who was fiercely protective of the school routine. “I think this attitude of not welcoming guests at all and every time hurts my dear Theo. I am placed in a dreadfully hard situation. But Westover does not exist as a monument to her genius, any more than it exists as an excuse for social pleasure