“kingdom.” The Hebrew can also be “reign,” “rule.”
“have reached their full measure of sin.” The Hebrew text is more literally, “when the transgressors have finished,” but it refers to completing their sin, which must refer to some measure of sin at which point God had had enough. The HCSB expands the text to read, “when the rebels have reached the full measure of their sin,” which gets the sense of the phrase.
“an insolent king.” The Hebrew text is more literally, a king “strong of face” or “of fierce face,” which is an idiom that can mean insolent, shameless (cp. Prov. 7:13), bold, and of firm conviction. This is a shameless and insolent person who will not be deterred from what he sets out to do by morals, laws, or shame.
“skilled in intrigue.” The Hebrew reads more literally, “understanding riddles” or “discerning unclear things,” but it is also an idiom in this context, because the biblical culture was one that loved riddles and sayings that were unclear. This man is not a riddle solver, or puzzle master, he will be a master of understanding what to do in difficult situations and understanding how to manipulate and control people. Thus, he is “skilled in intrigue” (HCSB; NAB; NASB); a “master of intrigue” (NIV; NLT); “understanding stratagems” (JPS); “deceitful” (NET); and “understanding hidden things” (YLT).