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 he would be called to answer for his vigorous pursuit of unconstitutional stop-and-frisk policing, for accusations against him of sexual misconduct, and for his history as a Republican. Ultimately, Bloomberg not only entered the race but has spent more than four hundred million dollars on political ads to defeat another New York billionaire, the incumbent. Randolph and Andrea Bernstein, a reporter for WNYC who covered Bloomberg’s three terms as mayor, sit down with David Remnick to discuss the candidate’s time in Gracie Mansion, his philosophy of governing, and his philanthropy. Whereas Trump’s political contributions have been unabashedly transactional, 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.”