Green hosted the nationally syndicated radio show "Both Sides Now" from 2010 to 2016. It aired on 200 stations and was recorded at IHeartMedia in New York City. The weekly program rotated such regular panelists as Arianna Huffington, Ron Reagan, Bob Shrum, Jonathan Alter, as well as Kellyanne Conway, Mary Matalin, David Frum, and Rich Lowry.. In February 2017 Green founded and ran the Twitter handle @ShadowingTrump, consisting of 21 leading national progressive scholars and former officials. It had 74,000 followers by the end of 2017.