Young traveled back to the Confederacy via Nova Scotia and Bermuda, where he proposed Canada-based raids on the United States as a means of building the Confederate treasury and forcing the Union Army to protect their northern border as a diversion.

Young was commissioned as a lieutenant and returned to Canada, where he recruited other escaped rebels to participate in the October 19, 1864, raid on St. Albans, Vermont, a quiet town 15 miles (25 km) from the Canada–US border.

Young ordered his troops to burn the town down, but the four-ounce bottles of Greek fire they had brought failed to work, and only one shed was destroyed.

There, the Lincoln administration retained prominent Irish-Canadian lawyer Bernard Devlin, QC, as counsel for the prosecution in the subsequent court case, which sought the raiders' extradition.

The court ultimately decided that the soldiers were under military orders and that the officially neutral Canada could not extradite them to America.

Young founded the first orphanage for black children in Louisville, a school for blind students, and did pro bono work for people experiencing poverty.

[4] In 1899, Young represented a formerly enslaved person, George Dinning, in a case against the Ku Klux Klan.