Finnegan's next two books grew out of assignments for "The New Yorker". In 1986, he was sent to Johannesburg, where he followed black reporters who gathered information for white reporters during Apartheid. This led to the 1988 publication of "Dateline Soweto: Travels with Black South African Reporters". "A Complicated War: The Harrowing of Mozambique", published in 1992, grew out of a series of correspondences about the war-torn nation for the magazine, and Finnegan's own travels throughout that war-torn nation. 1998 saw the publication of "Cold New World: Growing Up in a Harder Country", which deals with the bleak lives of American teenagers in spite of the United States’ economic affluence. It was a finalist for the New York Public Library’s Helen Bernstein Book Award for Excellence in Journalism in 1999.