Jack the lad

Origin of: Jack the lad

Jack the lad

British expression for a brash young man, a chancer, dates from the 1840s. The expression may be a reference to the famous Jack Sheppard, an immensely popular young criminal whose colourful life and multiple escapes from Newgate Prison generated legends well into the 19th century, long after his death on the gallows aged just 22 in 1724.