Jesus judgment against the Pharisees was that they scrupulously tithed even the smallest things (Leviticus 27:30), but they neglected the more important matters of the Law (Luke 11:42). The problem was they couldn’t count love for God and their fellow man (cf. Deuteronomy 6:4-9; Leviticus 19:18). Therefore, they neglected these more important matters, because they couldn’t measure them (cf. Mark 12:29-33). The whole of the Oral Law consisted of nitpicking matters similar to how far one could walk or how much one could carry on the Sabbath, and what constituted breaking one’s vow, and what was and what was not clean and other such matters.
The problem with the Oral Law, however, was it couldn’t nitpick about love, because love is generous, has an open hand, takes no thought of wrongdoing, and isn’t conceited etc. (Deuteronomy 15:8, 11; 1Corinthians 13:1-7). If a matter couldn’t show others how meticulously faithful the Pharisee was in obeying the Law (as interpreted by the Oral Law), he wasn’t interested in considering the issue. His whole religious life could be held in his hand, seen with the eye, heard with the ear etc., or in other words lived outwardly to be noticed by others. His self worth was summed up in the value others had of him.
The second woe Jesus pronounced upon the Pharisees concerned their love for the chief seats in the synagogues and the respectful greetings in the marketplaces (Luke 11:43). Their attitude contrasted with what they neglected to do in Luke 11:39-40, 42 (cf. 11:41). In the synagogues the chief seats were in front of and faced the congregation. This position, not only glorified their position above that of their brethren, whom they were commanded to love as one loves himself (Leviticus 19:18), but it placed their backs toward the cabinets which contained the scrolls of the word of God, thus expressing more love for themselves than for God whose word they had turned their backs to physically and, arguably, spiritually as well.
If we compare Luke 11:42 with Matthew 23:14 we would see that Jesus there added to his judgment of the Pharisees their taking advantage of widows. Luke doesn’t mention this, but it may be implied in his judgment of them concerning their love of respectful greetings in public. If the Pharisees had gained control of the inheritance of widows by becoming wise executors of a widow’s financial matters, they would have been guilty of aggrandizing themselves at the expense of the widows, whom they pretended to serve.
Jesus’ third judgment against the Pharisees (Luke 11:44) was that they were as graves, which, if a person walked upon, made him unclean (Numbers 19:16). In other words Jesus was saying the Pharisees were unclean and, as it were, filled with dead men’s bones (cf. Matthew 23:27-28). Their doctrines were unclean and made anyone who believed them unclean.
Jesus’ first two woes against the Pharisees constituted a personal judgment against them alone. Jesus revealed their sin, and their sin was theirs alone. On the other hand, the third woe involved other people who became ceremonially unclean, because they admired the Pharisees and believed what they taught. Since the doctrine of the Pharisees was false, it was unclean and ordinary people had inadvertently come in contact with an unclean matter, as though they walked upon a grave (cf. Numbers 19:16, 22).