This verse is among the strangest in the Torah, because it seems to contradict everything else the Torah says about the poor.
Targum Pseudo-Jonathan on Exodus (Exodus 23:3) is blunt: to the poor man who is guilty in his cause, thou shalt not be partial in having compassion upon him; for there must not be respect of persons in judgment.
Why Compassion Must Stop at the Courtroom Door
The Torah elsewhere commands mountains of concern for the poor. Leave the corner of your field. Cancel debts in the seventh year. Do not take interest. Open your hand wide. But when a poor man is a defendant in a lawsuit — and he is guilty — the judge must rule against him.
Why? Because the moment compassion distorts judgment, justice collapses for everyone. A judge who tilts the verdict toward the poor man has stolen from the wealthy man, even if he did it out of tender feeling. The Torah refuses to let the courtroom become a stage for private charity at someone else's expense.
The Private Remedy the Torah Prefers
This is why the Torah is so insistent about personal generosity. If you want to help the poor man who lost his case, pay his debt yourself. Feed his family. Take up a collection. But do it from your own pocket — not by bending the scales of the court.
The Takeaway
Compassion and justice are not the same thing, and the Torah refuses to blur them. A verdict must be true. Generosity, afterward, can be as wide as your heart allows.