In this oral history, Kevin Keefe reflects on his lengthy career as a bicycle courier, which began in mid-1980s and continued in several forms through the mid-2010s. Kevin also used his personal story to reflect on the myriad changes and shifts within both the courier community and the city at large. Kevin's route to becoming a courier was not always straightforward—he both spent a stint in the Navy during the Vietnam War, and he also worked for NASA for a stretch. A genuine love of the bike, however, kept his messengering career going for three decades, with periods of work punctuated by bicycle touring trips in the United States and abroad. Throughout his narrative, Kevin weaves both humorous and nerve-wracking anecdotes on the highs and lows of courier work, while also touching on alleycats, races that he liked participating in but never dominated. Kevin ends his narrative by reflecting on life in retirement—a medical condition keeps him from riding—costs of living in Washington, D.C., and the need for more cycling in order to mitigate climate change.