 Shepherd's legacy has been a matter of some debate since his death more than one hundred years ago.He has long been maligned as a corrupt, cronyist political boss, often compared to Boss Tweed, the leader of the Tammany Hall political machine of the same time period.A statue of Shepherd which currently stands on Pennsylvania Avenue, NW, in front of the John A. Wilson Building (which now houses the offices and chambers of the Council and the Mayor of the District of Columbia,) has served as a symbol of his fluctuating reputation.