On June 6, 1988, Olojede joined Newsday, the Long Island-based newspaper, as a summer intern. He eventually became a special writer covering minority affairs. In 1992 he began work on loan to the paper's foreign desk, making several trips to South Africa. He became the paper's United Nations bureau chief and then an Africa correspondent, based in Johannesburg, South Africa.
Olojede later worked as a correspondent in China, then returned to Long Island where he became foreign editor of Newsday. In 2003, Olojede took an opportunity to return to Africa as a correspondent to write about the 1994 Rwandan Genocide, ten years later.
In April 1994, when the genocide broke out in Rwanda, Olojede was covering the South African general elections, the first free elections at the end of apartheid. Olojede has said that while the South Africa story was important, he has often wondered if he could have helped the situation in Rwanda if he had gone there instead.
Olojede's 2004 series on the aftermath of the Rwandan Genocide was well received. One story that drew particular attention was "Genocide's Child" about a mother who was raising a son conceived during a gang rape during the war.
In 2005, Olojede won the Pulitzer Prize for International Reporting for his "fresh, haunting look at Rwanda a decade after rape and genocidal slaughter had ravaged the Tutsi tribe." The series was viewed as a major accomplishment for black journalists. Olojede was assisted by African American photographer J. Conrad Williams, and much of the series was edited by Lonnie Isabel, another African American journalist who was the assistant managing editor for national and foreign coverage.
By the time he won the Pulitzer, Olojede had already left Newsday. The Tribune Company had purchased Newsday from its previous owners in 2000, and by 2004 were trying to trim costs. At the end of 2004, Newsday offered a round of buyouts. On December 10, 2004, Olojede took the buyout and moved to Johannesburg, where he was living when he learned he had won the Pulitzer.
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