Chaucer's attitude towards the Five Guildsmen is not easy to determine and his portrait of them has been subject to many diverse readings. This chapter asks whether historical study of the medieval guilds brings us any closer to an appreciation of the resonances, for late-medieval readers, of Chaucer's text. In particular, we need to see the Guildsmen's fraternity in terms of contemporary debates about such associations and their secular and religious purposes. The poet himself does not preach or polemicize about the guilds or condemn them in the way that some of his contemporaries did. But the fact that the poet's account of the fraternity is not unambiguously positive is a sufficient clue that Chaucer was at least open to some of the contemporary criticisms of the guilds. His careful description of the Guildsmen provides both a comment and a contribution to this fourteenth-century debate.