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Writing
In addition to his articles in Inside Philanthropy, Callahan has written articles for The Washington Post, Los Angeles Times, The New York Times, Foreign Policy, The American Prospect, and The Nation.

In 2002, Callahan wrote Kindred spirits: Harvard Business School's extraordinary class of 1949 and how they transformed American business, a history of the Harvard Business School Class of 1949. In an interview about the book with The New York Times, Callahan contrasted this earlier group of business leaders, many of whom frowned on conspicuous consumption, with later generations of business leaders more motivated by greed.

A New York Times review of his 2004 book, The cheating culture: why more Americans are doing wrong to get ahead, Chris Hedges called Callahan "a new liberal with old values." The Cheating Culture is a nonfiction work that links the rise in unethical behavior in American society to economic and regulatory trends—particularly growing inequality. He lectured widely on the book to business groups and university audiences, frequently as a keynote speaker. The libertarian magazine, Reason, criticized Callahan for placing too much blame for cheating on the rise of laissez-faire economics.

His 2007 publication, The Moral Center, which examines how a market-based economy, i.e. capitalism, with its elevation of self-interest, undermines values that both liberals and conservatives care about. The American Prospect reviewed The Moral Center."

In his 2017 book  The Givers: Wealth, Power, and Philanthropy in a New Gilded Age which looked at top philanthropists such as Michael Bloomberg and Mark Zuckerberg. The book was widely reviewed, including in The New York Times, The Washington Post, The Wall Street Journal, Financial Times, Time, and The Atlantic. Callahan also appeared on NPR's Weekend Edition to discuss the book, as well as several local public radio stations, such as WNYC. Callahan appeared at events around the U.S. about the book, including at the New York Public Library, Town Hall Seattle, and the Commonwealth Club of San Francisco.

The Givers generated wide discussion and controversy in the world of philanthropy, including in industry publications such as Chronicle of Philanthropy, Sanford Social Innovation Review, and Philanthropy magazine. In a forum on the book in HistPhil, four experts in the field wrote essays sharing different perspectives on The Givers. HistPhil called The Givers "one of the more widely anticipated and widely discussed books on philanthropy in recent memory.'" While some critics said Callahan had written too positively about today's top philanthropists, others said that Callahan's ideas for reforming the charitable sector to limit the influence of private donors would be harmful. In an event at Philanthropy New York, Callahan engaged in a debate about the book with Emmett Carson, president of the Silicon Valley Community Foundation. Callahan also engaged in an online dialogues about the book with Sean Parnell, director of public policy for the Philanthropy Roundtable. In July 2017, Callahan responded to critics of the book in a lengthy essay in Inside Philanthropy.