“bring a case against.” The Hebrew word is riyb (#7378 רִיב, pronounced reeb), and it means to quarrel or contend, to lodge a complaint, to make a lawsuit against. In this context, the best meaning seems to be “bring a case, or lawsuit, against” (cp. HCSB; NASB; NIV; NRSV). On the basis of the Torah and the covenant God made with Israel, for example, the blessings and curses in Deuteronomy, it would seem that righteous people would do well and wicked people would suffer. However, in Jeremiah’s lifetime the opposite seemed to be the situation, so Jeremiah was “bringing his case” before Yahweh. Of course, like Job the righteous sufferer, God was always able to vindicate Himself. However, Jeremiah, like Job, complained to God about the situation.
We now see things much more clearly than Job or Jeremiah ever could. Jesus Christ made known God in a way that He had never been known before (John 1:18; Luke 10:24). Today we see the great war between Good and Evil, between God and the Devil. Also, the New Testament makes it clear that the Devil is the ruler of the world, which is why the world has the nature of the Devil and not the nature of God. It is because the Devil is the ruler of the world that “the world” hates followers of Christ, and neither Christ himself or his followers are “of the world” (John 15:18-19; John 17:14, 16). “The world” and the Father are opposed to one another (1 John 2:16), and the world is under the control of the evil one (1 John 5:19). [For more on the Devil being in control of the world, see commentary on Luke 4:6].
“Why does the road of the wicked prosper.” Godly people have noticed that wicked people often prosper, and have asked this same question for millennia (cp. Job 21:7-15; Ps. 10:3-11), but it has a good answer. Ungodly people are ruthless and often get ahead by evil and treachery. Also, being “of this world” they tend to pay closer attention to how to get ahead in life than godly people do, who are more interested in pleasing God and helping others than in buiding any kind of personal kingdom on earth. Furthermore, Satan, the god of this age, wants the wicked to be in charge and helps them in all kinds of ways. Job complained about the prosperity of the wicked some 1500 years before Jeremiah did (see commentary on Job 21:7).