In late 1902, exhaustion, financial distress, and the desire for a political appointment—combined with aspirations to serve as a broker for the export of African American labor abroad—led famed African American journalist T. Thomas Fortune to secure a temporary appointment with the Roosevelt administration to investigate trade and labor in Hawaii and the Philippines. In Hawaii, Fortune was fêted by the planter class, and allied himself publicly with the educational and political philosophies of Booker T. Washington. His hopes for black emigration and land ownership, however, were vigorously opposed by most newspapers connected to the oligarchy. Hawaii's robust in-language indigenous and ethnic newspapers, meanwhile, voiced their own position on black labor. In Manila, a fiercely entrepreneurial and militaristic American press attacked Fortune. Recent scholarship ties Washington's Tuskegee Institute to a kind of “Jim Crow colonialism” abroad. An in-depth look at Fortune's journey both supports and troubles such a view. Both men hoped U.S. “expansion,” and African American participation in it, might expose not only the power of race, but also its instability and vulnerability; Fortune, in particular, saw newspapers as vital to this task.