Our Gemara on Amud Aleph describes a despicable character type known as a rasha arum—a cunning wicked person—who exploits the law for morally questionable purposes. This type of person, the Gemara explains, is one who advises someone to sell property in line with the ruling of Rabban Shimon ben Gamliel, though not permitted to do so. The act is technically valid, but it deprives another designated party of their right to the property. This rasha arum is exploiting a legal loophole, and yet he derives no benefit nor has any good motivation; his cunningness is driven purely by the thrill of manipulating the system at another’s expense.

Rabbinic literature describes various forms of the rasha arum, all revolving around individuals who manipulate or subvert the law. For example, in Sotah (21b), we find that one who teaches a person how to manipulate legal claims to prevail in a Jewish court is considered a rasha arum. In secular legal systems, legal representation and technical maneuvering are expected parts of the process, but in Jewish law, sincerity and truth are paramount, and judges aim to discern the true nature of each claim. The rasha arum, however, distorts this by relying on legal technicalities to circumvent justice.

The most surprising example of this type of character appears in Bamidbar Rabbah (20), describing the actions of the wicked Bilaam. In an extraordinary moment, Bilaam tells the angel of God, “I have sinned,” knowing that the verbal confession alone would protect him from immediate punishment:

“Bilaam said to the angel of the Lord: I have sinned” – because he was a rasha arum, a cunning wicked person, he knew that confession has the power to ward off punishment, as anyone who sins and says, ‘I have sinned,’ is granted temporary reprieve.”

Eitz Yosef on the Midrash elaborates that Bilaam’s confession lacked true sincerity, as evidenced by his decision to continue his journey to curse the Jewish people despite claiming he had erred. He did not turn back; instead, he simply used the confession as a shield, understanding its protective power without any intention of genuine repentance.

This narrative reveals a remarkable principle about the power of verbal confession, even when insincere. To say the words “I have sinned” has a unique, protective quality; it carries an almost apotropaic power, creating a temporary barrier against punishment. The power of these words comes not from the speaker’s inner sincerity, but from the mere act of admitting fault, showing how significant it is in the cosmic scheme, even if the person confessing does so only for selfish gain.

Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation

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