While Winsey's education and connections gave him several advantages over other African Americans of that time, he still experienced discrimination due to his race. Although Winsey received his education from white institutions and had membership primarily in white organizations, an asterisk frequently appeared beside his name in the Baltimore City Directory indicating that he was "colored", thus effectively restricting his medical practice to the black community.
When Whitfield was a young boy, his mother Malvina died at the age of thirty-four. Whitfield's father soon remarried a lady by the name of Liddy. The new couple appear in the 1860 census with Winsey's brother Oliver (also known as William), but Winsey himself was not listed that year. Several sources stated he was privately educated, meaning he could have been away at boarding school when the census was taken. In 1866, William Winsey, his father, passed away, leaving Whitfield his considerable estate. Nothing more is known of William Winsey's second wife and younger son; perhaps she remarried and took Oliver with her.
The next year, 1867, Winsey worked under the tutelage of Dr. J. R. W. Dunbar. John Richard Woodcock Dunbar, M.D., was vice-president of the Medical and Chirurgical Faculty of Maryland at the time, and was later elected its president. Dunbar probably had a great influence on Winsey's acceptance into Harvard Medical School. As a graduate of the prestigious University of Pennsylvania Medical School and the founder of the Baltimore Medical Institute, Dunbar had important connections in the medical community which would prove of immense help to Winsey, the up-and-coming black physician. Winsey continued his medical studies through the late 1860s and early '70s. In the 1870 census, taken during the summer, Winsey (misspelled as "Whitfield Windsor") appears living with his aunt and uncle (Rachel and Ebenezer Gibbs) in the fifth ward of Baltimore City. His occupation was listed as "Medical Student". He listed his personal property value at the considerable sum of $8,500, presumably assets from William Winsey's estate.
Winsey graduated with an M.D. from Harvard in 1871. According to his obituary in the Afro-American, his diploma bore the signature of Oliver Wendell Holmes, a famous essayist, poet and professor of anatomy, and the father of the Associate Supreme Court Justice of the same name. Later that same year, Winsey married Anastasia Jakes.
Anastasia Jakes came from a large mulatto family of Roman Catholics. Her father, Henry Jakes, was a well-known barber and caterer. The Jakes residence and businesses were located at 121 St. Paul Street. Anastasia had nine brothers and sisters, one of whom became a teacher and another a music teacher. Several of her siblings took up occupations in line with the family business, such as wig maker, manicurist, and hair-dresser. Anastasia herself worked as a wig maker and ladies' hair-dresser out of her father's shop before she married Whitfield Winsey. A Baltimore Sun story of July 10, 1866, details an assault case in which Francis Lawn, a conductor on a city passenger trolley car, ejected Anastasia's mother Mary Ann Jakes on account of her race. The case was just one episode in the debate over segregated transportation facilities in the city during the age of Jim Crow. The Jakeses charged Lawn with assault, but the case was dismissed.
One indication of society's ambiguity toward African Americans was the inaccuracy of reporting in public records. The Winsey's marriage certificate, dated November 2, 1871, listed Anastasia's last name as "Jacques," although the city directories always list her and the other members of her family as "Jakes." The certificate also listed both Winsey and his bride as white! The fact that Winsey was a mulatto light enough to pass as white may have contributed to his success.
Research concerning the Winsey marriage allows a glimpse into the family's religious life and social ties. Winsey was an Episcopalian and Anastasia a Roman Catholic, but they were married in the Masonic Temple on Charles Street by a Unitarian minister, John F. Ware. Ware was himself a Harvard graduate and the founder of the Baltimore Association for the Moral and Intellectual Improvement of the Colored People. He had also appeared as a leader of the 1870 parade celebrating the ratification of the 15th Amendment. [Notice how the parade highlights community leaders.] Between Ware and Dunbar, it is evident that Winsey was traveling in circles of established whites with an interest in promoting African Americans. While just how Winsey came to be married by Ware is not known, the two may have known each other by both being Harvard alumni or from both being Masons. Non-Masons may not be married in the Masonic Temple, and it appears Ware had an official status as a clergyman in the Masons. Dr. Dunbar, Winsey's preceptor, was also a Mason, and was a Senior Grand Warden of the Grand Lodge of Masons from 1845 until his death four months before Winsey was married. Dunbar, in addition to probably assisting Winsey in his acceptance to Harvard, may have played a role in getting him accepted into the Masons, as well as the Chirurgical Faculty. Ultimately, Winsey's connections to the Medical and Chirurgical Faculty, the Masons, and to Harvard can all be traced neatly through the two persons of John F. W. Ware and John R. W. Dunbar.
Winsey's family changed in size and composition. In 1875 a son (Herbert) was born to Winsey, and a daughter (Bertha) followed in 1878. At least by 1880, if not from the beginning of Winsey's marriage, his maternal uncle and aunt, Ebenezer and Rachel Gibbs, lived with the Winseys, revealing a multi-generational family structure. In the 1880 census, the Gibbses were listed as Winsey's father- and mother-in-law. This might have been a result of the census taker's mistaking the older couple living with Winsey with a different last name than him as Winsey's in-laws. Winsey had no reason to report them as such, especially as Anastasia's parents were both still living. His father-in-law Henry Jakes did die in June of the following year. His will left all of his personal estate to his wife, Mary Ann Jakes, and stipulated that the proceeds of his estate after his wife's death were to be divided equally among all his living children. "Annastasia Winsey", as her name was spelled in Henry's will, was listed first among his children.
Two years after this high point in his career, death claimed both Winsey's aunt Rachel Gibbs and his wife Anastasia. Their deaths occurred within three days of each other: Rachel died on October 7th, and Anastasia on October 10th. After a nine days illness, Anastasia succumbed to tubercular meningitis, leaving her 6 and 9 year-old children motherless. She was 34, the same age as Winsey's mother at her death. Both Rachel Gibbs and Anastasia Winsey were buried in Laurel Cemetery, which is now lost, paved over as a parking lot. Rachel Gibbs's funeral was held at her brother's house at 110 Warner St, and was most likely an Episcopal service. Anastasia Winsey's funeral was held at the Winsey residence on East Fayette St., and Requiem Mass was offered on her behalf at St. Vincent's Roman Catholic Church. The next year, Winsey's uncle Ebenezer Gibbs married a woman named Jane M. Hages on December 15th and moved from Winsey's Fayette Street house to 22 East Street. Nothing more is known of Ebenezer's life except that he died nine years later, on November 11, 1894, and was buried in Laurel Cemetery. Whitfield Winsey was the medical attendant listed on his death certificate.
Winsey's adult children, Herbert and Bertha, lived with him, continuing the multi-generational structure of his family. His home certainly was large enough to accommodate them. In the 1898 directory, Herbert was listed as a clerk, and the next year as a printer. Bertha, according to the 1900 census, was a teacher, perhaps influenced by her maternal aunts Margaret, Rosa, and Mary F. Jakes, who had all been teachers or music teachers. Herbert was not listed in the 1900 census, but was in the directory for that year; he may have been enumerated at the printing office where he worked, the location of which has not yet been discovered.
Little had changed in Winsey's life by 1910. Herbert was still a printer, and Bertha was listed as a kindergarten teacher. The entire family, including their housekeeper Levinia Cooper, was again listed as white by the census taker in that year. The reason for their being reported as white is uncertain. Most likely, the census-taker made the decision to list them as white, not Winsey himself, he being obviously aware and proud of his race.
Whitfield Winsey died on July 6, 1919, two months short of his 72nd birthday. Dr. William T. Carr, Jr., one of the founders of Provident Hospital, was the medical attendant who signed Winsey's death certificate. The Afro-American printed a front-page story on his death, complete with photograph of him under the headline "Baltimore's Oldest Colored Doctor Dies After Long Illness." The article describes his funeral as follows: "The body was reviewed at the house on Tuesday and hundreds of friends paid their last tribute to an old Baltimorean. Funeral services were held from St. Katherine's Church, Wednesday morning at 10am. Father Devenish officiated. Pallbearers were Messrs. John Murphy, Solomon DeCoursey, Ernest Jiggs, Jas. W. Hughes and F. N. Cardoza."
In his will, Winsey left five-hundred dollars to his housekeeper, Levinia Cooper, his gold watch and chain to his son Herbert, and the rest of his estate, valued at nearly $24,500, to his daughter Bertha. Winsey did not explain why Bertha received the bulk of the estate, rather than his eldest son Herbert.
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