Raised in a small community of Black Nova Scotians, Jackson began his career as a commercial seaman at 16 years old and started a farm in his twenties.

He developed bronchitis, suffered a serious hand injury, and eventually received a Civil War Campaign Medal for serving during that conflict.

His grave remained unmarked until 2010, when a headstone was unveiled at an event attended by his great-great-granddaughter, Government of Nova Scotia officials, and American Civil War reenactors.

[2] His parents were freedom seekers who escaped slavery in the United States to British North America as refugees of the War of 1812, settling in Lower Horton (later renamed Lockhartville).

[6] In December 1863, Jackson left his farm to accept a position as ship's cook on the Saint John, New Brunswick–based Marlborough sailing to Liverpool, then to New York City.

[11] Jackson soon left New York, advancing to a new post on the USS Potomac,[4] an 88-gun frigate stationed as a receiving ship at Pensacola, Florida.

[12] Jackson was soon promoted, transferring to the USS Richmond,[4][5] a steam-powered, wooden sloop-of-war stationed off the heavily-fortified and Confederate-controlled Mobile Bay.

[5] On August 5, 1864, Farragut ordered his fleet into the bay, with the Richmond lashed to the starboard side of the wooden steamship Port Royal.

Confusion cascaded to the rest of the fleet until Farragut ordered the ships forward through the field of mines, which were called "torpedoes" at the time.

Following the command popularly remembered as "Damn the torpedoes ... full speed ahead", the Richmond proceeded into the bay and fired upon four Confederate steamships, three of which were captured by the US fleet.

[14] That September, Jackson served several days on a salvage crew working under difficult conditions on the wreck of a blockade runner.

[17] He returned home to Nova Scotia with US$900 (equivalent to about $18,000 in 2023) prize money from blockade runners he and his fellow sailors seized in the Gulf of Mexico.

[22] Jackson came home to Lockhartville, resuming work as a mariner on multiple Nova Scotia–based vessels on trips out of nearby Hantsport to the UK and the Mediterranean Sea.

[4] He developed and maintained relationships with many people throughout Hants and Kings Counties,[20] including William Hall,[4] a Royal Navy veteran who was also raised in Horton by Black refugee parents.

[27] He continued working his farm of 11 hectares (27 acres) and started selling fish, vegetables, and other goods as a peddler, transporting them on a black horse named Jack.

The issue was not settled until 1887 when the Pension Office received corroborating letters from the US consul in Halifax that added Jackson was "a worthy man instead of a nuisance whenever he comes to town".

[30] Jackson kept track of legislation at the United States Congress and applied for increases when eligible,[29] though the Pension Office raised the Saunders name issue almost every time.

[29] On June 12, 2010, a headstone at Jackson's grave was unveiled by one of his great-great-granddaughters at a funeral service designed to replicate elements common for Civil War veterans.

[18] The service was performed in period costume by the 20th Maine Reenactment Infantry Regiment, a group of American Civil War reenactors.

[34] At funerals they attend, the group fires volleys with replica muskets and adorns graves with Grand Army of the Republic plaques; a chaplain also speaks.