We remember the 2016 election as one of the most bruising, knockdown, polarized elections of our time, but behind the scenes, representatives for both Donald Trump and Hillary Clinton were quietly preparing each candidate to transition into office. Today, we speak with Ann O’Leary, co-executive director of the Clinton-Kaine Transition Project, and Rich Bagger, leader of the Trump for America transition operation, about what they learned from the 2016 transition, how to prepare for a transfer of power during a polarized election cycle and what advice they would offer this year’s candidates.  

Ann O’Leary is a longtime Democratic political figure and a self-described policy wonk. She has held a wide variety of roles over the past thirty years, beginning with serving on the Domestic Policy Council in Bill Clinton’s White House in the late 1990s. She then became legislative director for Hillary Clinton’s Senate Office before spending more than a decade at the Center for American Progress. She returned to politics with Clinton’s 2016 presidential campaign, first as a senior policy advisor and then as the co-lead of her transition team. Since then, Ann has worked outside national politics, practicing law and serving for two years as chief of staff to California Governor Gavin Newsom, during which she guided his transition into office and steered his administration through the COVID-19 pandemic. She now leads the Government Controversies and Public Policy Litigation Practice at the law firm Jenner & Block. 

Rich Bagger is a born-and-raised New Jersey corporate executive, politician and government leader. A lawyer by profession, he spent the 1990s and early 2000s as a New Jersey state legislator. From 2010-2012, he served as Governor Chris Christie’s chief of staff, using meticulous planning and political savvy to spearhead several legislative successes. Rich briefly returned to the private sector until 2016, when Christie, chairman of the Trump transition team, appointed him to run its day-to-day operations.

A complete transcript of the episode can be found here.