Jamieson, Fausset and Brown on Matthew 22:13

13. Then said the king to the servants--the angelic ministers of divine vengeance (as in Mt 13:41).

Bind him hand and foot--putting it out of his power to resist.

and take him away, and cast him into outer darkness--So Mt 8:12; 25:30. The expression is emphatic--"the darkness which is outside." To be "outside" at all--or, in the language of Re 22:15, to be "without" the heavenly city, excluded from its joyous nuptials and gladsome festivities--is sad enough of itself, without anything else. But to find themselves not only excluded from the brightness and glory and joy and felicity of the kingdom above, but thrust into a region of "darkness," with all its horrors, this is the dismal retribution here announced, that awaits the unworthy at the great day.

there--in that region and condition.

shall be weeping and gnashing of teeth. See on Mt 13:42.