Although a commonly recognized pathway to the U.S. Senate is through the U.S. House of Representatives, only four African American House members have run for the Senate since the passage of the 17th Amendment, and none have been elected. We examine why so few African American House members run for the Senate. Using an original dataset that includes all House members in the 102nd through the 110th Congresses, we explore the decision of House members, particularly African American House members, to run for the Senate. Despite the fact that so few African American House members have run for the Senate, our results raise doubts about the existence of direct race-based explanations. Instead, we demonstrate with mediation analysis that contextual factors linked to race, such as state population, ability to raise campaign funds, and ideological extremity, play an intervening role in the strategic decision to run. These findings have normative implications for descriptive representation.