born of women = brought forth by women (see note on Mat_1:2, Mat_1:16, Mat_1:18). A Hebraism (yelud 'ishshah). See Job_14:1; Job_15:14; Job_25:4.
least = less: i.e. younger, meaning Himself.
the kingdom. John was only proclaiming it (but not "in" it). The kingdom was rejected both as announced by John (Mat_3:2), by Christ (Mat_4:17), and by Peter (Act_2:38; Act_3:19-26); and, since its final rejection in Act_28:25, Act_28:26, is postponed, and is now in abeyance. See Heb_2:8 ("not yet"). The possessor is greater than the proclaimer.