To understand Obama’s legacy, walk in his shoes on the day it all began We assess Obama’s legacy by squinting into the future. Why not also look to the past? Check out this story on USATODAY.com: http://usat.ly/2iA3euJ WASHINGTON – We try to assess Barack Obama’s legacy by squinting into the murky future – debating the durability of his policies and programs, wondering what the new president will do to them.