[2][3] He established and published The Lyceum Observer, said to be the first newspaper in the Upper South to be owned and operated by an African American.

[2][4] He received his early education in the home of a wealthy sugar merchant and chairman of Baltimore's Chamber of Commerce, John C. Brunes, and his wife.

[3][4] He continued his education at the Maryland State Colonization Society,[2] went briefly to Liberia and Sierra Leone, and graduated in 1860 from Ashmun Institute (later known as Lincoln University) in Oxford, Pennsylvania.

[3][6] On September 29, 1864, the 3rd Division, including Fleetwood's regiment, participated in the Battle of Chaffin's Farm on the outskirts of the Confederate capital of Richmond, Virginia.

Now carrying the American flag, Fleetwood continued forward under heavy fire until it became clear that the unit could not penetrate the enemy defenses.

[13] Sara's maternal uncle, novelist Frank J. Webb, lived with the couple in Washington[14] in 1870 while writing for Frederick Douglass' New Era.

At first, the WCC was organized as a single company and commanded by Captain George D. Graham on June 12, 1880, when Fleetwood joined the corps as a commissioned officer.

The DCNG amalgamated seven battalions with four of them consisting of white members and three of them being "black" the Butler Zouaves (organized in 1863), the Washington Cadet Corps (1880), and the Capital City Guards (1882).

[19] When Frederick C. Revells from the Capital City Guards was made the new commander, Fleetwood felt passed over himself and resigned shortly afterward, in 1892.

[3][20] Meanwhile, Fleetwood and Major Charles B. Fisher, who had commanded the Fifth Battalion (Butler Zouaves), were instrumental in organizing the Colored High School Cadet Corps of the District of Columbia in 1888.

Supported by the community, including the wives of former presidents (Lucy Webb Hayes and Frances Folsom Cleveland), his musical presentations were extremely successful.

The interment was in Columbian Harmony Cemetery, Washington, D.C.[24] The First Separate Battalion of D.C. National Guards served as an escort at his funeral.

Among the honorary pallbearers were Major Arthur Brooks and such prominent Washingtonians as Daniel Murray, Whitefield McKinlay, and Judge Robert H. Terrell.

[27] His citations read: The President presented Sergeant Major Fleetwood the Medal of Honor because of his fearlessness during the Chapin's Farm, Virginia battle among his men in the 4th U.S.