South Boston is a densely populous neighborhood of Boston, Massachusetts, located south and east of the Fort Point Channel and abutting Dorchester Bay. One of America's oldest and most historic neighborhoods, South Boston was formerly known as Dorchester Neck and is today called "Southie" by its residents. Long known as a working class Irish-American neighborhood, it is also home to the Boston area's small but vibrant Polish and Lithuanian communities. South Boston contains Dorchester Heights, where George Washington historically forced British troops to evacuate during the American Revolutionary War. In addition to being home to some of the oldest housing projects in the United States, South Boston has also more recently seen property values join the highest in the city.

Geographically, Dorchester Neck was an isthmus, a narrow strip of land that connected the mainland of the colonial settlement of Dorchester with Dorchester Heights. Landfill has since greatly increased the amount of land on the eastern side of the historical neck, and widened the connection to the mainland to the point that South Boston is no longer considered separate from it. South Boston gained an identity separate from Dorchester, but the two were annexed by Boston in pieces, from 1804 to 1870.

Boston (pronounced /ˈbɒstən/ or locally /ˈbɔstən/ ( listen)) is the capital of and largest city in Massachusetts, and is one of the oldest cities in the United States. The largest city in New England, Boston is regarded as the unofficial "Capital of New England" for its economic and cultural impact on the entire New England region. The city proper, covering only 48.43 square miles, had a population of 617,594 according to the 2010 U.S. Census. Boston is also the anchor of a substantially larger metropolitan area called Greater Boston, home to 4.5 million people and the tenth-largest metropolitan area in the country. Greater Boston as a commuting region is home to 7.6 million people, making it the fifth-largest Combined Statistical Area in the United States.

In 1630, Puritan colonists from England founded the city on the Shawmut Peninsula. During the late 18th century, Boston was the location of several major events during the American Revolution, including the Boston Massacre and the Boston Tea Party. Several early battles of the American Revolution, such as the Battle of Bunker Hill and the Siege of Boston, occurred within the city and surrounding areas. Through land reclamation and municipal annexation, Boston has expanded beyond the peninsula. After American independence was attained Boston became a major shipping port and manufacturing center, and its rich history now helps attract many tourists, with Faneuil Hall alone attracting over 20 million every year. The city was the site of several firsts, including America's first public school, Boston Latin School (1635), and the first subway system in the United States (1897).

James Joseph "Whitey" Bulger, Jr. (born September 3, 1929) is a former organized crime figure from Boston, Massachusetts. Local folklore depicted Bulger as a Robin Hood–style social bandit dedicated to protecting the neighborhood and its residents. Bulger allegedly masterminded a protection racket targeting drug kingpins and those running illegal gambling operations. Based upon the testimony of former associates, Federal prosecutors have indicted Bulger for 19 murders.

Beginning in 1975, Bulger served as an informant for the Federal Bureau of Investigation (FBI). As a result, the Bureau largely ignored his organization in exchange for information about the inner workings of the Italian American Patriarca crime family. Beginning in 1997, the New England media exposed criminal actions by federal, state, and local law enforcement officials tied to Bulger. For the FBI especially, this has caused great embarrassment. On December 23, 1994, after being tipped off by his former FBI handler about a pending indictment under the RICO Act, Bulger fled Boston and went into hiding. For sixteen years, he remained at large. For twelve of those years, Bulger was prominently listed on the FBI Ten Most Wanted Fugitives list.