Alexander Roby ”Boss” Shepherd was born in Southwest Washington on January 30, 1835. He dropped out of school at an early age and eventually worked his way up to becoming the owner of a plumbing firm. He then invested his profits into real estate development, which made him a wealthy socialite and influencer in Washington D.C. One of his luxurious properties was Shepherd’s Row, a set of row houses on Connecticut Avenue, designed by Adolf Cluss.
In 1870, war and mismanagement had caused the finances and infrastructure of the city to deteriorate. As a solution, Shepherd and his allies began agitation for the abolition of the elected governments of Washington City and Georgetown to be replaced with a unified territorial government that would administer the entire District of Columbia.
Shepherd believed that if the government was to remain in Washington, the city's infrastructure and facilities must be modernized and revitalized. He filled in the long-dormant Washington Canal and placed 157 miles of paved roads and sidewalks, 123 miles of sewers, 39 miles of gas mains, and 30 miles of water mains. Under his direction, the city also planted 60,000 trees, built the city's first public transportation system in the form of horse-drawn streetcars, installed street lights, and had the railroad companies refit their tracks to fit new citywide grading standards for the District.
A statue of Shepherd which currently stands on Pennsylvania Avenue, NW, in front of the John A. Wilson Building, has served as a symbol of his fluctuating reputation. In 1979, the statue was removed and then reappeared in the mid-1980s near an otherwise-obscure D.C. Public Works building on Shepherd Avenue.
Shepherd will be remembered as an "urban visionary" who single-handedly transformed Washington into a major American city and championed aggressive social reform. The Shepherd statue now stands on its pedestal next to the sidewalk of Pennsylvania Avenue, NW, close to 14th Street, NW, and the northwest corner of the Wilson Building.