John the Painter (not to be confused with Peter the Painter, the Latvian anarchist/terrorist involved in the Sidney Street siege of 1911, in which Winston Churchill first won notoriety) was the nom de guerre of a Scot named James Aitken, born in Edinburgh in 1752. One of eleven siblings conceived in poverty, Aitken spent six years at a school for orphans and five years apprenticed to a painter before his career as a criminal began. He put in time as a highwayman and rapist, then spent two years (1773–75) in colonial North America as a redemptioner. This meant that the costs of his passage to the New World were advanced, but he was obliged to repay the debt within weeks of arriving in America; inevitably Aitken, like most others, failed to do so and was then auctioned off to the highest bidder.

As an indentured servant he was a slave in all but name, and escape from servitude was considered all but impossible. But Aitken, a man of great natural cunning, went walkabout and managed to get himself back to England. There he joined the Army,