In 1872, Winsey became the first black physician admitted to the Medical and Chirurgical Faculty of Maryland. His connections to Dunbar, even after Dunbar's death, served him well. Dunbar was held in high regard by his colleagues, as suggested by a resolution passed by the Faculty on July 12, 1871, printed in the Baltimore Sun the next day, which read in part ". . . in the death of Prof. Dunbar the faculty has lost a distinguished, faithful, and zealous member. . . always earnest in the promotion of the objects of the faculty and in the advancement of science during his long connection with this body." The resolution called him "an eminent teacher, a successful practitioner and a most honorable colleague, whose private virtue and large culture rendered him an ornament to the profession of medicine as well as to society." An article on Dr. Dunbar's death a week earlier in the Sun stated "He was preceptor of a large number of the graduates of medicine in this city, having as high as twenty-five students at one time in his office during the sessions of the medical college here. Many of his students have risen to eminence in the profession." Winsey may be fairly counted among those eminent students, especially as his accomplishments were not only of importance to his profession. With the memory of Dr. Dunbar so fresh in their minds, his colleagues at the Faculty helped Winsey in his efforts to gain recognition of his talents in the larger medical community. Through this accomplishment, Winsey was able to break down the barriers of race.
Little is known about Winsey and his family between 1890 and 1900 from sources other than city directories. However, in 1894, a group of prominent black physicians founded Provident Hospital on Orchard Street, which was the first private teaching hospital for blacks in Baltimore. In 1902 the hospital moved into two remodeled residences on Biddle Street. In 1899, Winsey applied for and was granted a permit from the Board of Medical Examiners of the State of Maryland. More research is needed to determine why a permit was needed at that time, or whether African Americans had recently gained the right to receive such permits. Winsey was an instructor at Provident, which provided teaching for colored internists. The dates of Winsey's service at Provident will be found among the hospital's records at the Allen Mason Chesney Medical Archives of the Johns Hopkins Medical Institutions.
In 1901, Winsey became the treasurer and physician for the Industrial Home for Colored Girls at Melvale, a post which he held for eighteen years until his death. According to his biography in the Medical Annals of Maryland, Winsey was also a Delegate to the International Medical Congress at Washington. In addition, Winsey was the author of several papers before the Faculty, the Clinical Society of Maryland, and the Medical Congress. Sometime before his death in 1919, Winsey also became a member of the American Medical Association. Note that although Winsey was employed as a physician at black institutions such as the Melvale Home and Provident Hospital, he belongs to white fraternal and professional organizations. Perhaps Winsey saw entry into traditionally white organizations as a way to further break down racial barriers, or to further his career. Perhaps his sponsors saw helping Winsey as a contribution to the advancement of his race, and perhaps his light skin color made that process easier. Membership in such societies indeed had a positive influence upon his career, although Winsey was unable to cross the color bar and work in white institutions.
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