Charles Wilson Fleetwood

This 1855 painting of Charles Wilson Fleetwood was part of an exhibit at the National Portrait Gallery in 2018. It belongs to the Howard University Art Museum.

Charles Wilson Fleetwood Jr.

As a young man, Thomas Waterman Wood apprenticed with his father, a cabinetmaker, who trained him to make drawings for furniture orders. Once Wood's technical abilities developed, he went to Boston to take classes in the studio of the prominent portrait artist Chester Harding. This training enabled him to make a living through portraiture.

Wood ran a portrait studio in New York City but ultimately settled in Baltimore. Around this time, Maryland was known to have eighty-four thousand free persons of color. Art patron John C. Brune commissioned Wood to create this portrait of his butler Charles Wilson Fleetwood Jr. (life dates unknown), among other African American subjects. -- NPG

Overlapping with the museum label above, Moss, Ward and Fagg in their 2017 book The Sweat of Their Face say this about Charles Fleetwood and this painting:

Ultimately, Wood settled in Baltimore. where he portrayed many African American subjects. Maryland at this time was known to have 84,000 free persons of color, many of whom lived in Baltimore. Art patron John C. Brune commissioned Wood to create this portrait of his domestic worker and “chief steward” Charles Wilson Fleetwood Jr., among other African American subjects. These portraits were later exhibited at the National Academy of Design, and the acclaim they brought Wood furthered his reputation and career. 

Fleetwood is portrayed in a dignified manner. Apparently in control of his work environment and engaging the viewer directly with a confident pose and a good-natured expression. Fleetwood was born “a free Negro” in Baltimore in 1812 and died there in 1884. Between 1842 and 1846, Baltimore city directories listed him as a “bay trader,” “barber of hair,” “waiter,” “confidential servant,” and “Negro Householder”. -- Moss, Ward and Fagg.