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The area around 14th and U streets has been an important center for business, civil rights, and politics since the turn of the 20th century. Fourteenth Street, a major public transportation route, was home to automobile dealers, major grocery stores, and restaurants, as well as civil rights organizations after World War II. It has also been called a "gateway to the best of Washington's black community." Arthur Ashe once said, "The corner of 14th and U was the grapevine. The cream of black society and everybody else passed through there, so if you were at 14th and U, you knew where the parties were, you knew who was in town, you knew if there was trouble. If you were at that corner, you always had the sense that something big was about to happen."

The reputation of 14th and U helps explain the numerous public protests against segregation and racism practiced by white-owned businesses there. In 1941 Sanitary Grocery (now Safeway) opened at 14th and U with no black clerks. The New Negro Alliance, an organization started in 1933 by young black men who instituted "don't buy where you can't work" campaigns in predominately black areas, picketed the chain until clerks were hired a few months later. Similar protests occurred during the Great Depression (1929-1941) and after World War II.

By the 1960s, the National Association for the Advancement of Colored People (NAACP) and the Student Non-Violent Coordinating Committee (SNCC) were two of the civil rights groups with offices near the intersection.

During the 1968 riots, when African Americans responded to the assassination of the Rev. Martin Luther King, Jr., and the federal government's apparent abandonment of the city, 14th and U was one of the city's major hotspots. In 1986, during the Marion Barry Administration, the Frank D. Reeves Center for Municipal Affairs was completed here. The center honors lawyer Frank D. Reeves (1916-1973) and anchored the restoration of the historic intersection.

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