In the case of John the Baptist, and of countless believers since his time, doubt might better be described as perplexity or confusion. The perplexity dealt with in these verses is the perplexity of a believer, a true child of God and citizen of His kingdom. John was not questioning the truthfulness of God’s Word as revealed in the Old Testament or as revealed to him at the baptism of Jesus. He was rather uncertain about his understanding of those truths. Virtually all the gospel references to doubt pertain to believers rather than to unbelievers; and the kind of questioning John the Baptist experienced concerning Jesus’ identity can only occur in the life of a believer. In that transitional time, before the written revelation of the New Testament, there were many things that seemed unclear and needed explanation and confirmation.
Humanly speaking the career of John the Baptist had ended in disaster. He had been the fiery, independent, dramatic, confrontational, courageous man who preached exactly what needed to be preached, to whom it needed to be preached, and when it needed to be preached. He was fearless, aggressive, and faithful to the Lord in every way. He called sin sin and sinners sinners. And now he was in prison because of his faithfulness.
On a trip to Rome, Herod Antipas, governor of Galilee, had taken a liking to Herodias, the wife of his brother Philip, and had seduced her. After returning to Galilee, Herod divorced his own wife and married Herodias. When John the Baptist heard of it, he publicly confronted Herod with his sin anti was promptly thrown into prison. Only Herod’s fear of the multitudes kept John from being killed immediately (Matt. 14:5).
John was imprisoned at an old fort at Machaerus, located in a hot and desolate region five miles east and fifteen miles south of the northern end of the Dead Sea. He was placed in a dark, stifling dungeon that was little more than a pit. After some eighteen months in the limelight, this free spirit of the wilderness was confined and isolated. He had been in prison for perhaps a year when he sent the two disciples to Jesus.
William Barclay captures much of the significance of John’s situation:
He was the child of the desert; all his life he had lived in the wide open spaces, with the clean wind on his face and the spacious vault of the sky for his roof. And now he was confined within the four narrow waits of an underground dungeon. For a man like John, who had probably never lived in a house, this must have been an agony. In Carlisle Castle there is a little cell. Once long ago they had put a border chieftain in that cell and had left him for years. In that cell there is one little window, which is placed too high for a man to look out of it when he is standing on the floor. On the ledge of the window, in the stone, there are two depressions worn away. They are the marks of the hands of the border chieftain, the places where, day after day, he had lifted himself up by placing his hands on the ledge that he might look out on the green dales across which he would never ride again. John must have been like that; and there is nothing to wonder at, and still less to criticize, in the fact that questions began to form themselves in John’s mind. (The Gospel of Matthew, vol. 2 [Philadelphia: Westminster, 1958], p. 2)