On six occurrences (8:12; 13:42; 13:50; 22:13; 24:451 and 25:30), Matthew recorded Jesus pronouncing judgment utilising the idiom weeping and gnashing of teeth. Although the majority of commentators acknowledge the uniqueness of this phrase, virtually none deal with its function within Matthew’s gospel or theology. This gap in the literary landscape of Matthean literature marked the bifold rationale of this literary study, namely, to investigate the nature and function of this Matthean maxim, and consequently, seek to deduce its contribution to the theme of apocalyptic judgment in Matthew’s Gospel.