According to the Burl Ives Songbook John Webb and Bill Tenor were jailed in Salem, Massachusetts around 1730. The imprisonment was unpopular and a mob freed them. A twenty verse broadside appeared shortly after the raid.
Historical records indicate John Webb was a counterfeiter. The Boston Evening Post of October 16, 1738 relates that John Webb, of Salem Massachusetts, was apprehended passing counterfeit five pound notes of Rhode Island. He escaped but was found hiding in his mother's attic in Salem. Webb was released from jail in November 1738 due to insufficient evidence. There is no indication that a mob broke him out of jail.
An alternate explanation from Lomax's Folk Song of North America is that there was a dispute in the colonies in the 1730's about the basis for currency. The old paper money (called tenors) was based on Spanish coinage which brought varying prices in various colonies. When parliament decreed that new paper money (new tenor) were to replace the old (old tenor) disturbances broke out in Massachusetts. John Web was mint-master in Salem Massachusetts and stuck to the 'old tenor'. He was jailed for the offence but was rescued from prison by a group of his friends. Someone reworked an old Scottish ballad "John o' Cawfield" to celebrate the event.
I learned this from the Kingston Trio recording and the Burl Ives Songbook. It was also printed in Lomax's Folk Songs of North America.