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NASB (UPDATED) TEXT: Mat_16:1-4
1The Pharisees and Sadducees came up, and testing Jesus, they asked Him to show them a sign from heaven. 2But He answered and said to them, "When it is evening, you say, 'It will be fair weather, for the sky is red.'3And in the morning, 'There will be a storm today, for the sky is red and threatening.'Do you know how to discern the appearance of the sky, but cannot discern the signs of the times? 4An evil and adulterous generation seeks after a sign; and a sign will not be given it, except the sign of Jonah." And He left them and went away.
Mat_16:1 "the Pharisees and Sadducees" Matthew links these two groups together as the collective leadership of rabbinical Judaism (cf. Mat_3:7; Mat_10:1; Mat_10:6; Mat_10:11-12; Mat_22:34). For a full discussion of the origin and theology of the Pharisees, see note at Mat_22:15 and for the Sadducees see Special Topic at Mat_22:23.
▣ "testing" This word (peirasmos) was used with the connotation of "test with a view toward destruction" (cf. Mat_6:13; Jas_1:13).
See Special Topic at Mat_4:1.
▣ "a sign from heaven" "From heaven" is a circumlocution for "God." They had seen His miracles but they wanted more (cf. Mat_12:38-42). This was the same temptation offered by Satan in Mat_4:5-6 about winning mankind's allegiance by the use of the miraculous.
Apparently these Jewish religionists wanted evidence that Jesus was empowered by YHWH. They were calling the healings "Satan's work," so they wanted a sign that was indisputably from God (i.e., "heaven"). Exactly what that would be is not clearly stated. Jesus gives them that sign, but in a veiled and future way (i.e., His resurrection).
Mat_16:2-3 These sentences are not in the most ancient uncial Greek manuscripts à , B, X, and the Greek text used by Origen, the Greek manuscripts known to Jerome, nor in some Peshitta or Coptic versions, but they are found in the uncial manuscripts C, D, L and W. A similar passage is found in Luk_12:54-56. The textual critics behind the fourth edition of the Greek NT put out by the United Bible Societies could not make a decision about the originality of these verses (cf. A Textual Commentary on the Greek New Testament by Bruce Metzger, p. 41.)
Mat_16:3 "the signs of the times" Notice the PLURAL " times." This refers to the two ages (see Special Topic at Mat_12:31). These Jewish religionists could predict and understand some weather phenomena, but they could not/would not understand the coming of the new age of the Spirit in Jesus. He chides them for their lack of spiritual perception (cf. Isa_6:9-10). Another sign/prophecy was fulfilled in them!
Mat_16:4 "adulterous generation" This phrase is used in the metaphorical sense of "unfaithful." The metaphor (cf. Mat_12:39; Jas_4:4) goes back to the OT usage related to idolatry and fertility worship (i.e., Jer_3:8; Jer_9:2; Jer_23:10; Jer_29:23; Ezekiel 23; Hos_4:2-3; Mal_3:5).
▣ "the sign of Jonah" They would have had no clue what He was talking about! This was an analogy of three days Jonah was in the great fish and Jesus would be in Hades (cf. 1Pe_3:19). Remember Jesus was in the tomb only about thirty-six to forty hours, but it was reckoned as three days in the Jewish counting system of Jesus' day. Part of a day was counted as a whole day and a day began and ended at twilight (cf. Genesis 1). See notes at Mat_12:39 and Mat_16:21.