Interesting question. In Ireland the highwaymen were often seen as folk heroes, continuing a tradition of guerrilla warfare against the British. By the 18th century they were often called "Rapparee" which was the original name for the pike-wielding (rapparee comes from the Gaelic for "pike-wielder") supports of James in the Glorious Revolution. So by 1720 the highwaymen that had taken on this moniker were not seen as criminals by the local Irish.