This chapter focuses on the task President Jefferson assigned Robert Patterson, i.e., to find a translator for two Arabic manuscripts written by Muslim slaves. Over a few days in late October 1807, Patterson consulted with three of the most remarkable figures he could find in Philadelphia, a triad that represented diplomacy, trade, and academia. The three men each had their own reaction, reflecting their professional interests and personal experiences, as well as individual prejudices. In October 1807, the two manuscripts constituted a type of “Rorschach test” for surprised American reviewers. Although visiting these three various men, first in Patterson’s mind was the single man whom Jefferson himself had named. In the race against time to translate Arabic writings, Philadelphia was home to an American whose years of experience in Arabic-speaking regions exceeded all others, Richard O’Brien.