Born in Nicholasville, Kentucky, in 1843, Bennett H. Young was 18 years old when he enlisted as a private in the Confederate 8th Kentucky Cavalry, a unit that became a part of General John Hunt Morgan's cavalry command. Young was captured while on Morgan's daring 1863 raid through Indiana and Ohio and was imprisoned at Camp Douglas near Chicago. After one failed escape attempt Young was sentenced to an underground dungeon for 30 days, but he succeeded in escaping on his second try and fled to Canada. Placed in charge of a number of other escaped Rebel prisoners in Canada, Young successfully ran the blockade with them, returning to the Confederacy through the port of Wilmington, North Carolina.

In June 1864 Young was promoted to lieutenant and recruited to return to Canada, where he became a part of several secret service missions. He clandestinely returned to Chicago in July as part of a plot to liberate the Camp Douglas prison camp. The plan failed because a spy in the rebels' midst revealed the plot to Union authorities. Young then became involved in a plot to liberate Camp Chase at Columbus, Ohio, but when that plan also failed to materialize, he returned to Canada. In October Young commanded a successful raid by 20 young Confederate escaped prisoners from Canada to St. Albans, Vermont, where the fugitives robbed three banks of over $200,000. They returned to Canada and turned over the money to agents of the Confederate government before being arrested by Canadian authorities. Canada, refusing U.S. demands for extradition, tried the raiders, found them not guilty, and released them.

At the end of the war, Young was excluded from President Andrew Johnson's amnesty proclamation and could not return home until 1868. He spent his time abroad studying law and literature at the University of Ireland and the University of Edinburgh. When finally allowed to return to the United States, Young became one of the most prominent attorneys in Louisville, Kentucky.

Young was reported to have lived an exemplary life. He was never known to play cards, use tobacco, drink, or utter a word that could not be repeated before any woman.

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