1)

What is the meaning of "b'Hishafto Yetzei Rasha"?

1.

Rashi: When [my hater] is judged in front of You, his verdict should be liable and [he is called] a Rasha.

2.

Radak: If he (the head of the Resha'im who hate me) has a judgment with anyone, he should come out a Rasha. I.e. he should stumble in his words and claims.

3.

Malbim: Sha'ul will judge me evilly, and they will prosecute against me, and sentence me to death.

2)

Why does it say "u'Sefilaso Tihyeh la'Chata'ah"?

1.

Radak #1: When he prays for himself, his prayer should not be a merit, rather, like a sin and a liability.

2.

Radak #2: "La'Chata'ah" is like "El ha'Sha'arah v'Lo Yachati" (Shoftim 20:16) - it should not be accepted.

3.

Malbim: The custom was to supplicate in front of the judge for Chesed. They say that also [David's] supplication should be like sin, and not be accepted.

Sefer: Perek: Pasuk:

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