Second Street, or "the Deuce," in Richmond's historic Jackson Ward neighborhood, was the focal point of African American commerce in the early part of the 20th century. Enterprises of all types clustered along this street, just north of Broad Street, Richmond's main thoroughfare and the center of White business activity. While some scholars have argued that there was, in fact, never a separate Black economy, it is clear that this street was the hub of African American economic and social life in Richmond. Professional and personal services, banks, hotels, restaurants and general merchandise stores were established along Second Street to meet the needs of Richmond's Black population. Denied access to the White-owned theatres and clubs, Blacks also created a unique entertainment district along the Deuce, which was home to numerous social clubs, restaurants, and theatres. This paper explores the growth of Second Street during the first half of the 20th century and explains the reasons behind its subsequent decline in the latter half of the 20th century.