Medieval Chester has been stigmatised by post-medieval writers and academics as a militarised 'Wild West' town full of ruffians and criminals. This thesis investigates whether that reputation is justified. Three categories of evidence are systematically evaluated: the Domesday laws, the records of proceedings from Chester's four medieval city courts - the Crownmote, the Portmote, the Pentice Court and the Passage Court - and references to Chester in medieval texts. Findings from the city's Mayors' and Sheriffs' Books, the Cheshire Outlawry Rolls, Trailbaston proceedings and the Bishops' Registers are also assessed. It is clear from these sources that, while the centuries wrought some changes and assault was not uncommon, throughout the Middle Ages the proportion of violent offences perpetrated by citizens of Chester was comprehensively dwarfed by the trading offences, property transactions and debts which formed the bulk of cases handled by the City Courts. The examination of medieval chronicles and other literary sources confirms that contemporary commentators did not view Chester as particularly lawless. Comparisons with the national state of law and order in medieval England strengthen the contention that Chester was no more criminal or militarised than any other medieval city.