This chapter examines what Trump might gain from perpetually evaluating others in his verbal interactions. The analysis presented here explores Trump’s evaluations of his guests at the 2017 Black History Month Listening Session. The political stakes of the event were high, as the President who had been repeatedly accused of racist and xenophobic remarks led a meeting of Black Americans in celebration of Black historical figures. Yet during the event, Trump repeatedly placed himself in the role of “evaluator” and positioned his guests as “evaluatees.” With each guest likely noticing that their own turn to be evaluated was soon at hand, each worked to provide Trump ample evidence of their fealty in exchange for his positive evaluation. Their demonstrations of commitment and loyalty to Trump garnered his praise only when the guests provided evidence that mets Trump’s implicit criteria, which he repeatedly modeled in his evaluation of others around the table. As a result, Trump and guests worked together on the fly to achieve his position as “Evaluator in Chief” and further solidify his public image as the “Boss.”