Howard Wolfson is the former Deputy Mayor of New York City, counselor to former NYC mayor Michael Bloomberg, co-chief strategist and communications director on Hillary Clinton’s 2008 presidential campaign, and currently leads the Education division of Bloomberg Philanthropies. He joins David to talk about his mother’s battle with chronic depression, his decision to abandon journalism and pursue political strategy, the New York City media market and Donald Trump’s instinctive mastery of it, his experience working for Chuck Schumer, Hillary Clinton, and Michael Bloomberg – and the possibility of a 2020 presidential bid from Bloomberg.

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