James Winthrop, son of Professor John Winthrop of John Adams' student days, served as college librarian from 1772 until 1787, when he was eased out of the position. His eccentricities, contentiousness, and overbearing manner rendered him intolerable to colleagues and students (see entry of 7 July 1787, below). John Quincy Adams was, however, quick to perceive the range of Winthrop's intellectual interests, seeing him as the only college official “who for genius and learning, would make a figure in any part of Europe.” On the other hand, he criticized the “old bachelor” for being “without one particle of softness, or of anything that can make a man amiable,” particularly for his alleged severe remarks “upon the ladies.” Once married, Adams added, “He will be more esteemed and beloved than he is now, he cannot be less.” Winthrop's outside activities in politics and the law provided college authorities with the opportunity to rid themselves of the brilliant but troublesome and intemperate man. A viiisuccession of judicial posts culminated in the chief justiceship of the Middlesex Court of Common Pleas, but his major concerns remained with learning. He was an original member of the Massachusetts Historical Society. Winthrop willed his library of over three thousand volumes to the fledgling Allegheny College in western Pennsylvania. The portrait used here is one Allegheny's president Timothy Alden repeatedly requested of Winthrop's brother and finally received “to accompany the books” (Sibley-Shipton, Harvard Graduates , 17:317–329; JQA to JA, 21 May–14 June 1786, Adams Papers; JQA to AA2, 18 May–17 June 1786, AA2, Jour. and Corr. , [3]: 116–117; Lawrence Shaw Mayo, The Winthrop Family in America, Boston, 1948, p. 251–252).