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Diggins taught history at San Francisco State University until 1969, when he took up an offer at UC Irvine. There, he served as an associate professor. In 1972, Diggins began at City University of New York Graduate Center (CUNY), where he stayed for two decades, until taking over as acting director of the Graduate Center from 1996 to 1997. Diggins held for a time the chair in American Civilization at the École des hautes études, Paris, and was a visiting professor at Cambridge and Princeton Universities. Additionally, Diggins was a consultant and frequent lecturer at University of London and Columbia University.
Aside from teaching, Diggins wrote dozens of books and articles, starting with Mussolini and Fascism in which Diggins describes the popularity of the Italian leader prior to World War II. Diggins then took newly formed ideas of the American left to publish The Rise and Fall of the American Left and Up from Communism, which proposed that leftist ideals grew worldwide through a series of eruptions and events through history and were later exported to other countries, giving birth to movements such as Marxism. Diggins was also critical of the New Left and even tougher on the academic left, which that followed. He derided the trendy ideas of Michel Foucault and Jacques Derrida.
Up from Communism describes four prominent liberal doctrinaires who flipped ideologies by embracing conservatism. Diggins continued to write articles and other books on intellectual history for the next 30 years.
In his best-seller Ronald Reagan: Fate, Freedom, and the Making of History, Diggins asserted that Reagan was treated dismissively and that his virtues were indeed liberal. That was contrary to Diggins's personal experience of Reagan "standing for tear gas and police" most likely in reference of the 1960s Berkeley protests.
Diggins said that his view on Reagan changed after he had read his writings that were released after Reagan's death. Diggins concluded that Reagan was "far from conservative" and more on the liberal side of the spectrum. Instead of the previous notions about him, Diggins wrote, "Reagan was the great liberating spirit of modern American history, a political romantic impatient with the status quo."
Diggins topped off with Why Niebuhr Now? describing the shifting political loyalties of Reinhold Niebuhr; written posthumously, the book was released in 2011.
An obituary reported that Diggins "was "critical of the anticapitalist Left for seeing in the abolition of property an end to oppression" but also "critical of the antigovernment Right for seeing in the elimination of political authority the end of tyranny and the restoration of liberty." He stated, "I am left of right and right of left."
Diggins was a consultant on various films and documentaries, including "Between the Wars;" "Reds;" "John Dos Passos;" "The Greenwich Village Rebellion"; " Emma Goldman;" "The New York Intellectuals;" "The Future of the American Left;" and "Il Duce, Fascismo e American" (Italian television). Diggins also appeared in numerous interviews with C-SPAN.
Diggins's three marriages ended in divorce. As a California native, he lived in Laguna Beach, California, for years while he taught at UC Irvine. Later, Diggins lived in the Upper West Side. He died on January 28, 2009, in Manhattan after a battle with Colorectal cancer. He is survived by his companion of 15 years, the author Elizabeth Harlan; a son and a daughter, both from his first marriage; two sisters; and two grandchildren.
Diggins's interests ranged from the foundations of the United States to the postmodern world. He declared Ronald Reagan to be "one of the two or three truly great presidents in history."
After Diggins's death, the John Patrick Diggins '53 Endowed Scholarship was created in his name at Sacred Heart Prep in San Francisco
In a review of Diggins's Ronald Reagan: Fate, Freedom, and the Making of HistoryRich Lowry, editor of the National Review wrote,
Diggins seems blinded by Reagan's sunniness, which, in this interpretation, was not just a matter of temperament, but reflective of a deep philosophical and religious conviction. Reagan, Diggins maintains, sought to rid "America of a God of judgment and punishment." This is absurd. Reagan had a charitable view of human nature and a relaxed, nonjudgmental air, but there is no denying his deeply felt social conservatism. He wrote - as a sitting president, no less - the anti-abortion tract "Abortion and the Conscience of the Nation."