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[[File:ESCobbWWIRegistrationCard.jpg|thumb|right|200px|Cobb's 1918 World War I Draft Registration Card]]
Cobb began practicing medicine in Pensacola in January 1916, becoming one of just seven black doctors then working in the city.<ref name="harmony" />
Shortly after returning to Pensacola, Cobb was arrested in July 1916 for violating the city's "Jim Crow" law segregating streetcars. A conductor on the Bayshore Line asked a group of black riders to vacate seats for white passengers, and Cobb allegedly either didn't oblige the request or was slow to move.<ref>"Allege Violation of 'Jim Crow' Law." ''Pensacola Journal''. 5 July 1916.</ref>
In March 1918, Cobb entered the U.S. Army and was sent to France just before World War I ended. While in France, Cobb attended classes at the University of Leon and interned at the Hospital Dieur, in addition to providing healthcare to ten small French villages and four companies of soldiers. Cobb was discharged from the Army in April 1919 and resumed his practice in Pensacola. Cobb aspired to become a surgeon, but was not allowed to join the all-white staff of [[Pensacola Hospital]].<ref name="harmony" />