When Logan Pearsall Smith—brother of the future Mary Berenson—thought back to his university years in the 1880s, he observed that “the atmosphere of Harvard was at that time … richly coloured by the sense of social differences. The prestige possessed by members of the most exclusive clubs, the delight of being seen in their company, and the hope of being admitted into their select circles, these were the animating motives of life at Harvard as I knew it.”  One such organization was the literary society known as the O.K. Club (or Orthoepy Klub), which included Bernard Berenson, Charles Loeser, and George Santayana. For their early friendship with Berenson, and for their own considerable accomplishments, Loeser and Santayana deserve special mention in the “cast of characters” of Bernard Berenson’s Harvard years. Later, however, the men parted ways. In 1941, Berenson described Loeser as “my most fierce enemy-friend and would be competitor, as well as really fine collector”;  and as early as 1912 Santayana condemned I Tatti as full of “ultra-learned and judging aesthetes” and “soulful tourists and weary dilettanti.”  A fitting home, one might think, for a former member of the O.K. Club.
Charles Alexander Loeser (1864–1928; fig. CC.I.9)
Loeser was born 11 January 1864 in Brooklyn, New York, into a family of Jewish-German immigrants who arrived in the United States in the middle of the nineteenth century.  American by birth, Loeser spent the greater part of his life in Florence, in the villa Torri Gattaia on the hill of San Miniato al Monte, devoting himself principally to the study of art history and collecting. Notwithstanding his scant scholarly output, he worked at many major institutions, such as the Gabinetto Disegni e Stampe degli Uffizi in Florence and the Albertina in Vienna, to study the most important European art collections. His own collection ranged from ancient to contemporary art, with an emphasis on the Italian fifteenth and sixteenth centuries, and included various artistic genres and techniques.  Indeed, Loeser was one of the major American collectors of Italian art between the end of the nineteenth to the beginning of the twentieth century. After his death, much of the Loeser collection was dispersed due to the Second World War and through sales at auction.  A group of works of art and furniture from the Renaissance, on view at the Palazzo Vecchio, Florence, offers a sample of Loeser’s precious collection.  Loeser’s last will and testament left those works to the city of Florence in 1928 on the condition that the rest of his property could be freely exported by his heirs. He also provided for the donation of eight Cézanne paintings to the White House, and 262 drawings to the Fogg Art Museum, Harvard University, Cambridge.  No in-depth or systematic analyses have been made of Loeser, though some recent studies have focused on specific aspects of his collecting and studies, especially his knowledge of drawings and pioneering discovery of Cézanne.  Surely an important aspect of Loeser’s life and work is his connection to Berenson, which was marked by successive moments of unity and opposition.
The lively entrepreneurial spirit of Frederick Loeser, the father of Charles and a magnate in the textile industry, enabled his family to achieve economic success in the United States in a short time.  Charles was thus able to complete his initial studies at an international institute in Switzerland, where he mastered both German, his native language, and French. In 1882, he was admitted to Harvard, where he showed special interest in history and philosophy. After receiving his bachelor of arts degree in 1886, with excellent grades, Loeser continued his studies for another two years and earned a master of arts in philosophy. 
Firsthand information on Loeser’s experience at Harvard is scarce, and much of it comes from the account of his close friend George Santayana (1863–1952). A common interest in literature, art, and philosophy brought them together: the two friends met, above all, to discuss books or assist at theater and opera performances.  Their relationship was intense but desultory because of Loeser’s complicated character: young, brilliant, and generous, he was also evasive, impenetrable, and considered a loner.  Santayana interpreted this “detachment” to Loeser’s Jewish origins, a heritage he never hid. This must have made Loeser “uncomfortable” in a university context, where, at the time, most Jews concealed their background and presented themselves as Christians or atheists.  Loeser, nonetheless, did not seem to suffer because of his isolation; this resulted not from external forces but his choice to be dedicated totally and exclusively to the world of art and literature. “In America,” Santayana affirms, Loeser “floated on the surface, and really lived only in the international world of art, literature, and theory.” 
Not surprisingly, a sense of harmony developed between Loeser, Santayana, and Berenson. Berenson, like Loeser, was of Jewish origin; Santayana, a Spanish immigrant, was also considered “different.” Though Berenson was a bit younger than the others, the three quickly became friends, sharing many aspects of university life and, above all, membership in various cultural circles. They formed part of the O.K. literary society (The Orthoepy Klub), a cultural circle that provided an alternative to the athletics tradition at Harvard.  Loeser was among the first members of the Harvard Art Club, which was established in 1873, transformed in 1885, and closed in 1890.  The club, complete with a library, was open to all Harvard students interested in the history of art and offered readings and public gatherings devoted to the discussion of art-historical problems. At the first meeting, in which Loeser took part, the architectural merits of the Memorial Hall of Boston were discussed with James Russell Lowell and Charles Eliot Norton (fig. CC.I.11). 
Loeser’s interest in the art world was precocious. From his early years at Harvard he had been collecting books and paintings, and in 1887–1888, he enrolled in optional courses in art history taught by Norton.  He also appears to have attended William James’s course (fig. CC.I.7) in English philosophy and Josiah Royce’s course “Modern Discussion of the Philosophy of Nature.”  The list of books he borrowed from the Harvard library not only indicates his interests and the direction of his studies, but also the courses he attended. In 1885, he took a course on moral philosophy with George Herbert Palmer, which included the study of Kant, and another on French literature with Ferdinand Bôcher and the assistant Adolphe Cohn, which included the analysis of Jean Racine. The book loans also evince Loeser’s profound interest in theater. His main field of concentration was, in any event, philosophy, and in 1888, he traveled to Berlin  to deepen this direction of his studies. Perhaps he was influenced by Santayana, who was in Berlin between 1886 and the summer of 1888 on a Walker Fellowship.
By 1890 Loeser had moved to Florence, where he remained the rest of his life. There he maintained or established ties with many figures associated with the Harvard art world, including Norton, James, and Jean Paul Richter. Significantly, in light of his later donations to the Fogg, Loeser knew Edward Forbes, several years before the latter became director in 1910, as well as Paul Sachs, a member of the visiting committee, whom Loeser met in Italy in 1914. Loeser maintained an enduring correspondence with both, probably crucial for his decision to make a return trip to the United States between 1922 and 1923.  On that occasion, Loeser visited both the Fogg and the Museum of Fine Arts, Boston. His second and last trip in America dates from 1928. On 15 March of that year, Loeser died in New York from a pulmonary infection. His body was brought back to Italy and buried in the Florentine Cimitero degli Allori, where a memorial built by the sculptor Antonio Maraini records Loeser’s musical, literary, and artistic interests.
George Santayana (1863–1952; fig. CC.I.12)
George Santayana is considered one of the major philosophers of the twentieth century.  He was born in Madrid on 16 December 1863 from the second marriage of Josefina Borrás, the widow of George Sturgis, with the Spanish government official Agustín Ruiz de Santayana. He passed his childhood with his father in Spain, in the city of Avila. In 1872, he embarked on a trip overseas to join his mother, who had moved to Boston with the children from her first marriage. Integration into the new environment was not easy, and at first he had great difficulty communicating in a foreign language. Santayana soon overcame this obstacle, however, and later mastered the English language. Like Bernard Berenson, he attended the Boston Latin School and continued his studies at Harvard University; in 1886, he obtained a bachelor of arts degree summa cum laude and, in 1889, a PhD in philosophy.  From that point on, Santayana focused on the development and articulation of his own philosophical theory, expressed in a number of publications written in English. A prolific and versatile writer, he produced work in many genres, including philosophical texts and criticism, essays, and even poems; his first poetic work was Sonnets and Other Verses, published in 1894. His writings enjoyed considerable success, in particular his first essay on aesthetics, The Sense of Beauty (1896), and the philosophical novel The Last Puritan (1936). The most extensive and systematic works, which established his reputation in studies of philosophy, are his five-volume The Life of Reason (1905–06) and the four-volume Realms of Being (1927–40). In three significant philosophical-autobiographical texts—Persons and Places: The Background of My Life (1944), The Middle Spain (1945), and the posthumous My Host, the World (1953)—Santayana reflected on the important events of his life, describing the many people and places he encountered. He sketches memorable representations, rich in detail, of a few friendships that matured while he was at Harvard, such as that of Charles August Strong.  In 1886, the two were in Berlin on a Walker fellowship, which was offered to graduate students who wished to study philosophy in Germany. Santayana’s stay there, lasting through the summer of 1888, is documented in letters with his parents, college friends (including Logan Pearsall Smith, fig. CC.I.13), and university professors, above all Charles Eliot Norton (fig. CC.I.11) and William James (fig. CC.I.7).  James was Santayana’s most influential of Santayana’s professors at Harvard, where he also studied with Royce and Palmer. James also directed him to university teaching,  despite their different philosophical positions.
A record of Santayana’s Berlin sojourn survives at I Tatti: a small pen and ink portrait, by an unknown hand, inscribed “G Santayana / Berlin, May 24.88.” This small sketch, perhaps a gift of Santayana to Berenson, attests to the lasting connection between the two.  Nevertheless, Berenson appears rarely in the memories sketched by Santayana in Persons and Places. He was described as an “old friend” only when Santayana deals with the theme of his first trips in Italy and of Americans living in Europe. Instead, his autobiography provides useful information on less noted figures and those for whom documentary material is lacking, such as Loeser. The two shared literary and poetical interests, as well as a feeling of “isolation” from the world that made them both “different.”  The condition of the “outsider,” a term Santayana used to express his perpetual state of dissonance in Boston society and the Harvard community, remains a constant trait of his personality, as well as “philosopher-vagabond” and “external observer of the world.”  In spite of this, he found the university campus a familiar, enjoyable, and inviting place. As he wrote in a letter of 26 January 1935, “I acted in the Institute and Hasty Pudding plays at Harvard, dressed as a leading lady and a ballet dancer, I was devoted (as a spectator) to football, and had for years, after I was an instructor, many close friends among the under-graduates. I also went a good deal into what was called “Boston Society.” So that my solitude (which was real) was only latent.” 
Santayana was registered in eleven clubs in all: he was founder and president of the Philosophical Club; collaborated in drafting the Harvard Monthly, the periodical in which Berenson also had his literary debut; worked as a cartoonist for The [Harvard] Lampoon; and joined the O.K. Club.  From his father, who had been introduced to painting by a student of Goya, Santayana developed a passion for drawing. At Harvard, he even entertained the idea of becoming a painter, a thought soon undermined by the desire to continue his philosophy studies. 
For Santayana, Harvard was not only the institution where he began his philosophical training, but also the place in which he began his university career. After he earned his PhD with a dissertation on Hermann Lotze, under the supervision of Royce, Santayana was hired as an instructor, later advancing to assistant professor and finally achieving rank as full professor.  Although considered a brilliant professor, he did not particularly enjoy university teaching because it was not adaptable to his character and too bound by the conventions of the academic world. These limitations led him to break his relationship with Harvard University in 1912. In that same year, he left the United States for Europe. He stayed in England and in France, frequently visited Italy, and, in his travels to Florence, was the guest of the Berensons at I Tatti. In 1923, he established himself in Rome, and from there he maintained an occasional and irregular exchange of letters with the Berenson family. The bond between Berenson and Santayana turned cold following a meeting in Venice in 1939, when Santayana insulted Berenson for his unbounded social and intellectual ambition.  This event, which has been read as an excess of jealousy by Santayana toward Berenson’s popularity and lifestyle (“like a lord”),  compromised the subsequent relations between the two friends. Santayana’s last visit to I Tatti was in 1921. After that, particularly after the encounter in Venice in 1939, Santayana no longer frequented the salon of Berenson’s home. As for Berenson, he never really understood Santayana’s disparaging attack and continued, even in the years following, to esteem the philosopher and consider him one of his “first college companions.”  Santayana lived his last years in Rome, in extreme solitude. In 1941, he voluntarily retired in isolation to a convent run by Irish nuns at Celio, where he died on 26 October 1952.
Acton, Harold. Memoirs of an Aesthete. London, 1984.
Announcement of Courses of Instruction provided by the Faculty of Harvard College for the Academic Year 1887â€’88. Cambridge MA, 1887.
Arnett, Willard E. “Santayana and the Fine Arts.” The Journal of Aesthetics and Art Criticism 16, no. 1 (1957): 84–95.
Ashmore, Jerome. “Santayana’s Mistrust of the Fine Arts.” The Journal of Aesthetics and Art Criticism 14, no. 3 (1956): 339–347.
Bardazzi, Francesca, ed. Cézanne a Firenze: Two Collectors and the 1910 Exhibition of Impressionism. Exhibition catalog, Florence, Palazzo Strozzi. Milan, 2007.
Bosco, Nynfa. Invito al pensiero di Santayana. Milan, 1987.
Cory, David. The Letters of George Santayana. New York, 1955.
Francini, Carlo. “L’Inventario della Collezione Loeser alla Villa Gattaia.” Bollettino della società di studi fiorentini 6 (2000): 95â€’127.
———. “Palazzo Vecchio: L’Invenzione del museo.” Bollettino della società di studi fiorentini 7–8 (2000â€’2001): 131â€’143.
———. La Donazione Loeser. In Palazzo Vecchio. Officina di opere e di ingegni. Cinisello Balsamo, 2006.
Harvard College. Class Secretary’s Report. The Fiftieth Anniversary of the Class of ’86 and the Three Hundredth of the College. Boston, 1936.
Holzberger, William G., and Herman J. Saatkamp, jr. Persons and Places: Fragments of Autobiography. Introduction by Richard C. Lyon. Cambridge MA and London, 1986.
Lensi, Alfredo. La Donazione Loeser in Palazzo Vecchio. Florence, 1934.
Mannini, Lucia, ed. Le Stanze dei tesori. Collezionisti ed antiquari a Firenze tra Ottocento e Novecento. Exhibition catalog, Florence, Palazzo Medici Riccardi. Florence, 2011.
McComb, K. Arthur. The Selected Letters of Bernard Berenson. Boston, 1964.
McCormick, John. George Santayana: A Biography. New York, 1987.
Morgan, Agnes. “The Loeser Collection of Drawings.” Bulletin of the Fogg Art Museum 2, no. 2 (1933): 22â€’24.
Oberhuber, Konrad. “Charles Loeser as a Collector of Drawings.” Apollo 107 (1978): 464â€’469.
———. Old Master Drawings: Selections from the Charles A. Loeser Bequest. Cambridge MA, 1979.
Osborne, W. John. “Intellectual Jealousy: Berenson and Santayana.” Modern Age 44, no. 3 (2002): 288–291.
Patella, Giuseppe. Bellezza, arte e vita. L’estetica mediterranea di George Santayana. Milan, 2001.
Rivalta, Benedetta. “La donazione Loeser al Comune di Firenze negli anni 1942â€’1946.” La Casa dei doganieri. Rivista di libri, lettere, arti 2, no. 1 (2009): 77â€’84.
Saatkamp, J. Herman, Jr., and John Jones. George Santayana: A Bibliographical Checklist, 1880–1980. Bowling Green, Ohio, 1982.
Samuels, Ernest. Bernard Berenson: The Making of a Connoisseur. Cambridge MA, 1979.
Santayana, George. Persons and Places: The Background of My Life. New York, 1944.
———. Persons and Places: The Middle Span. New York, 1945.
SkowroÅ„ski, Krzysztof Piotr. “Santayana and the Avant-garde: Visual Art in the Context of Democracy, Norms, Liberty and Social Progress.” Bulletin of The George Santayana Society, no. 29 (2011): 14–19.
Smith, Logan Pearsall. Unforgotten Years. London, 1938.
Stiles, H. Reed. The Civil, Political, Professional and Ecclesiastical History and Commercial and Industrial Record of the County of Kings and the City of Brooklyn. 2 vols. New York, 1884.
Tordella, Piera Giovanna. “Charles Loeser, Die Handzeichnungen der königlichen Bibliothek in Turin. Connoisseurship, collezionismo, cultura della conservazione dei disegni antichi tra Otto e Novecento.” Annali di critica d’arte 5 (2009): 231â€’276.
 Smith 1938, 103.
 Letter of Bernard Berenson to Mrs. Alfred Barr, 22 April 1941, as cited in McComb 1964, 182.
 Osborne 2002.
 Stiles 1884, 1104.
 Francini 2000.
 Rivalta 2009.
 Lensi 1934.
 Morgan 1933; Oberhuber 1979; Francini 2000–2001; Francini 2006, 312–319. For a brief, updated profile of Loeser and the collection he donated to the city of Florence, see the entry by Serena Pini in Mannini 2011, 165–172.
 Bardazzi 2007.
 Stiles 1884, 1104.
 Harvard College. Class Secretary’s Report 1936, 280–281.
 Santayana 1944, 224–237.
 Ibid., 226–227.
 Ibid., 224, 230–231.
 Ibid., 227; Acton 1984, 62: “Art interested him [Loeser] far more than human beings.”
 Samuels 1979, 33–34.
 Oberhuber 1978, 465.
 Ibid., 465.
 Santayana 1944, 255.
 Announcement of Courses of Instruction 1887.
 Morgan 1933: 22.
 Oberhuber 1978: 466.
 For an introduction to Santayana’s thought and an outline of his biography, see McCormick 1987 and Bosco 1987. The literature on Santayana is vast; for those before 1980, see Saatkamp and Jones 1982. A Santayana Society, founded in 1980 in the United States, annually publishes a newsletter dedicated to the study of his thought and is responsible for the critical edition of his work.
 Santayana 1944, 253; Santayana 1945, 152â€’153.
 Charles Augustus Strong (1862–1940), a theology and psychology scholar, was a professor at University of Chicago and Columbia University. At the end of his academic career he moved to Italy, where he lived in Villa Le Balze, Fiesole.
 Santayana 1944, 249â€’254; Santayana 1945, 132â€’139.
 William James, in particular, pushed Santayana to make the best of his efforts in Germany and produce tangible results. See Santayana’s letter to William James, 3 July 1888, in Cory 1955, 30.
 Santayana 1945, 153, 166â€’170.
 Samuels 1979, 33â€’34.
 Santayana 1944, 226.
 Ibid., 186; Santayana 1945, 113.
 Santayana to F. Champion Ward, 26 January 1935. See Cory 1955, 292. Santayana’s isolation was therefore “latent” and in line with his vision of a “world explorer” both errant and cosmopolitan. See Lyon in Holzberger and Saatkamp 1986, XVIIIâ€’XXX.
 Santayana 1944, 197â€’202; Samuels 1979, 29.
 Santayana 1944, 226. In connection to this, within the elaboration of Santayana’s aesthetics, is his thought on the figurative arts. See Ashmore 1956; Arnett 1957; Patella 2001; SkowroÅ„ski 2011.
 Santayana 1945, 158â€’159.
 There is a letter from Santayana to Bernard (dated 1925), and five letters from Santayana to Mary (four dated 1904, one dated 1930) in the Bernard and Mary Berenson Papers, Biblioteca Berenson, Villa I Tatti—The Harvard University Center for Italian Renaissance Studies.
 Osborne 2002.
 Ibid., 290.