In February 2009, U.S. Secretary of State Hillary Clinton named Bosworth a Special Representative for North Korea policy.

[8] Prior to 1984, his previous foreign service assignments include Paris, Madrid, Panama City, and Washington, D.C. where he was the State Department's Director of Policy Planning, Principal Deputy Assistant Secretary for inter-American affairs, and Deputy Assistant Secretary for Economic Affairs.

[1] Before his appointment as ambassador to South Korea, he was the executive director of the Korean Peninsula Energy Development Organization (1995–1997).

[1] He served on the executive committee of Americans Elect, a political party seeking to gain ballot access in every state in 2012.

[11][12] On January 4, 2016, Bosworth died at the age of 76 due to pancreatic cancer in Boston, Massachusetts.