By day, Brodie was a respectable tradesman and Deacon (president) of the Incorporation of Wrights, which controlled the craft of cabinetmaking in Edinburgh, and this made him a member of the town council.

He used the money he made dishonestly to maintain his second life, which included a gambling habit and five children by two mistresses, who did not know of each other and were unknown in the city.

He reputedly began his criminal career around 1768, when he copied keys to a bank door and stole £800, then enough to maintain a household for several years.

In 1786 he recruited a gang of three thieves: John Brown, a thief on the run from a seven-year sentence of transportation; George Smith of Berkshire, a locksmith who ran a grocer's shop in the Cowgate; and Andrew Ainslie, a shoemaker.

[1] The case that led to Brodie's downfall began on 5 March 1788, when he organised an armed raid on the excise office in Chessels Court, on the Canongate.

Brodie hurried home, changed into more normal clothes, and went to the house of his mistress Jean Watt, on Libertons Wynd, hoping to create an alibi.

[1] On the same night, Brown approached the authorities to claim a King's Pardon, which had been offered after a previous robbery, and gave up the names of Smith and Ainslie (initially saying nothing of Brodie's involvement).

Realising that he had to leave Edinburgh, Brodie travelled southwards and reached Dover in 18 days, closely pursued by George Williamson, a King's Messenger.

Endeavor was returning to Edinburgh, but Brodie paid the ship to detour and drop him off in Flushing, the Netherlands, whence he travelled to Ostend.

At first there was no hard evidence against Brodie, although the tools of his criminal trade (copied keys, a disguise, and pistols) were found in his house and workshops.

Of this, William Roughead in Classic Crimes states that after research, he was sure that although the Deacon may have had some hand in the design, "...it was certainly not of his construction, nor was he the first to benefit by its ingenuity".

However, Stevenson remained fascinated by the dichotomy between Brodie's respectable façade and his real nature, and this paradox inspired him to write the novella Strange Case of Dr Jekyll and Mr Hyde, which he published in 1886.

In 1989, Bathgate rock band Goodbye Mr Mackenzie wrote and recorded a track titled "Here Comes Deacon Brodie", which appeared on the B-side to their hit "The Rattler".