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That Herbert Simon in 1987 chose to have Richard Rappaport paint his official portrait, instead of the more famous artist Philip Pearlstein, who simultaneously paints Carnegie Mellon University's president, suggests Dr. Simon's enduring enthusiasm for the younger artist's work that reaches as far back as 1964 during Rappaport's junior year when the artist makes a lithograph of Simon's daughter Barbara and the following year when the artist paints a large Simon Family portrait.

That Herbert Simon, from the very beginning of their thirty-five year friendship, put his enormous prestige behind the then undergraduate student, explains in part, along with Rappaport's very close ties to Robert Lepper, the unusual status of the young artist, not only within the College of Fine Arts, but on campus.

And it explains the unique circumstances of Rappaport's two solo exhibitions held in the vast central hall of Skybo, the university center (since demolished) after he had graduated, when on returning to Pittsburgh in the autumn of 1966 after having painted Ship of Fools in New York City that summer, the twenty-two year old artist, just by asking, is given the privilege to hang it, Six Characters in Search, Jewess Accused, and Rose of Washington Square that November, and then again that following February 1967 to hang the just completed Oratory Mural.