Eleanor Randolph finished her biography of Michael Bloomberg in June, 2019, just as the former mayor decided not to run for President. “He didn’t want to go on an apology tour,” Randolph tells David Remnick. Bloomberg knew that he would be called to answer for his vigorous pursuit of unconstitutional stop-and-frisk policing, accusations against him of sexual misconduct, and his history as a Republican. Ultimately, Bloomberg did enter the race, and he has spent more than four hundred million dollars on political ads to defeat another New York billionaire, the incumbent, Donald Trump. Randolph and Andrea Bernstein, a reporter for WNYC who covered Bloomberg’s three terms as mayor, join Remnick to discuss the candidate’s time in Gracie Mansion, his philosophy of governing, and his philanthropy. Trump’s political contributions have been unabashedly transactional, but Bloomberg’s generous philanthropy also has an expected return. “All the money that he gave to philanthropies and charities were a way of doing good in the world, sure, but they were also a way of making him more powerful as mayor,” Bernstein says. “Everything with Bloomberg, there’s a countervailing thing. Something benefits somebody: it also might benefit him, it also might benefit billionaires from Russia.”

Eleanor Randolph is the author of “The Many Lives of Michael Bloomberg.” Andrea Bernstein’s book is “American Oligarchs: The Kushners, the Trumps, and the Marriage of Money and Power.”