The original Smart Alec was a New York pimp, Alec Hoag, who operated in the 1840s. Partnered by his wife, Melinda, the couple would rob her “customers” while she otherwise distracted them.
They started simply enough by luring victims into dark alleys with the promise of a quick fumble but all they ended up with was Hoag relieving them of their property. Inevitably, some of the victims went to the police but Hoag simply cut some of the officers into a share of the spoils. His undoing started when financial difficulties caused him to renege on his arrangement.
Hoag further refined his technique by operating a scam known as the panel game con. The victim was lured to his apartment by Melinda who persuaded him to remove his clothing and put them on a chair at the head of the bed near a secret panel. When everything was ready, Melinda would close the curtain. Hoag would then rife through the victim’s clothes and relieve him of all his valuables. Soon afterwards, Hoag would bang on the door and Melinda would make out that her husband was returning, causing the victim to vacate the premises post. haste.
The police soon caught on to Hoag and arrested him and Melinda. However, Hoag managed to escape with the assistance of his brother but was soon recaptured.
Hoag was given the nickname “Smart Alec” by the police for being too clever for his own good. The phrase was then applied to other felons exhibiting the same level of craftiness and if first found its way into print in 1865.