From Faith Futures
Lachs [Rabbinic Commentary on the New Testament], (254f)...
many will come from east and west. A Semitism using the opposites to include everything. Cf. Ps. 106.3; cf. Mark 1.11 ...
to sit at table. Actually "to recline at table." Gr. anaklithesontai = Heb. basev. The meal in the NT symbolizes the joys of the kingdom, and this idea goes back to Jewish sources about the messianic banquet, which included among other dainties Leviathan and Behemoth ...
sons of the kingdom. In the NT only here and in Matt 13.38. This phrase is not found in rabbinic sources, but in the same vein are the phrases "Who is the son of the world-to-come?" and "son of the covenant." This phrase is most difficult. The "son of the kingdom" or the rabbinic "son of the world-to-come" refers to one who inherits his portion because of merit or by faith and is used in a posiitive not a negative sense. Dalman, however, states: "The sons of the theocracy are those who belong to it in virtue of their birth, who thereby have a natural right to possession of it." Also, Allen: "'Sons of the kingdom' is a Semitic idiom equivalent to those who should inherit it, its rightful heirs." ... Abrahams' comments ... The "sons of the kingdom" in this passage "no doubt, signifies the Jewish nation or people. Such of them as are lacking in the faith which the centurion possessed will be cast out of the kingdom, whilst Gentiles sit down with the righteous patriarchs at the banquet."
into outer darkness. Darkness as punishment is met with frequency in Jewish sources: "Into darkness will your spirits enter" (En. 103.8);, "Those who were born in darkness will be cast into darkness" (En. 108.14); "their inheritance is darkness" (Ps. Sol. 14.6); "the inheritance of the sinner is darkness" (Ps. Sol. 15.11); "He will send back the ungodly into darkness" (Sib. Or. 4.43). In rabbinic literature these are also of note: "God calls Gehenna darkness" (Lev. R. 27); "The sinner in Gehenna will be covered with darkness" (Exod. R. 14.2).
men will weep and gnash their teeth. A common phrase in Matt., cf. 13.42,50; 22.13; 24.51; 25.30; and only once in Luke, 13.28. That the sinners in Gehenna weep is well known, e.g., "the transgressors will cry and make lamentation" (En. 108.3), "the voice of crying and weeping and lamenting and strong pain" (En. 108.5), "the mighty hell-full of lamentation" (En. 40.12).