My 500 Extraordinary Days in the Trump White House. After standing at Donald Trumps side on Election Night, Cliff Sims joined him in the West Wing as Special Assistant to the President and Director of White House Message Strategy. He soon found himself pulled into the Presidents inner circle as a confidante, errand boy, advisor, punching bag, and friend - sometimes all in the same conversation. As a result, Sims gained unprecedented access to the President, sitting in on private meetings with key Congressional officials, world leaders, and top White House advisors. He saw how Trump handled the challenges of the office, and he