After the city was established, much of the former Young plantation was purchased by a Bostonian venture capitalist named James Greenleaf, who received a discount on sixty thousand real estate lots in exchange for a promise to build ten new houses on them per year.

[citation needed]) As a result, except for a few scattered buildings such as Thomas Law's (a land speculator who was able to put down pounds sterling) and workers' shanties, settlement of the Southwest Waterfront was extremely slow.

He also initiated the construction in 1802 of the Washington City Canal, which connected Tiber Creek, at the western foot of the National Mall, with the Anacostia River—then called the "Eastern Branch"—just east of the Arsenal.

The canal opened in 1815 but was too shallow and subject to unstable tides to be useful as the industrial pipeline Law had hoped for; instead, it quickly filled with trash and stagnant water, isolating the Southwest from the rest of the city.

The Waterfront developed a thriving commercial district with grocery stores, shops, a movie theater, as well as a few large and elaborate houses—mostly owned by wealthy blacks— but most of the neighborhood was a very poor shantytown of tenements, shacks, and even tents.

[4] In the 1950s, city planners working with the Congress decided that the entire Southwest quadrant should undergo significant urban renewal — in this case, the city would acquire nearly all land south of the National Mall (except Bolling Air Force Base and Fort McNair), either through voluntary purchases or through the use of eminent domain, evict virtually all of its residents and businesses, destroy many of its streets and all of its buildings and landscapes, and start again from scratch.

There was some opposition to the plan, notably from the Southwest Civic Association, because of its emphasis on building luxury housing rather than supplying low and moderate-income dwellings to replace the homes slated for demolition.

However, the redevelopment plans, which had been crafted by architects Louis Justement and Chloethiel Woodward Smith and included modernist buildings, ample green spaces, and plenty of parking, were popular among many city residents and officials, and their appeal eventually won out.

Only a few buildings were left intact, notably the Maine Avenue Fish Market, the Wheat Row townhouses, the Thomas Law House, and the St. Dominic's and Friendship churches.

The heart of the urban renewal of the Southwest Waterfront was Waterside Mall, a small shopping center/office complex mostly occupied by a Safeway grocery store and satellite offices for the United States Environmental Protection Agency.

The Southwest Neighborhood Library was first opened in 1940 as part of the then-new Thomas Jefferson Memorial Junior High School[13] and then reopened in its current location in 1965.

[18] On March 19, 2014, developers PN Hoffman and Madison Marquette broke ground on a massive redevelopment of D.C.’s Southwest Waterfront into a mixed-use complex named "The Wharf".

[22] Current and former residents of Southwest D.C. include the late House Representative John Conyers and former Police Chief Charles H. Ramsey[citation needed].

Hubert Humphrey lived there while serving as U.S. Vice President, and Thurgood Marshall, Lewis Powell, and David Souter all had homes in Southwest during their tenures on the United States Supreme Court.