Our Gemara on Amud Aleph records Shimon ben Shetach’s bemused reaction to the famous Choni HaMeagel’s antics in prayer.  We are all familiar with Choni’s petulant demands of God during a drought, refusing to leave a circle he drew until God made it rain, according to his specific requirements.  Shimon ben Shetach said, 

שָׁלַח לוֹ שִׁמְעוֹן בֶּן שָׁטַח: אִלְמָלֵא חוֹנִי אַתָּה — גּוֹזְרַנִי עָלֶיךָ נִידּוּי. אֲבָל מָה אֶעֱשֶׂה לְּךָ, שֶׁאַתָּה מִתְחַטֵּא לִפְנֵי הַמָּקוֹם וְעוֹשֶׂה לְךָ רְצוֹנְךָ כְּבֵן שֶׁהוּא מִתְחַטֵּא עַל אָבִיו וְעוֹשֶׂה לוֹ רְצוֹנוֹ, וְעָלֶיךָ הַכָּתוּב אוֹמֵר: "יִשְׂמַח אָבִיךָ וְאִמֶּךָ וְתָגֵל יוֹלַדְתֶּךָ".

Were you not Ḥoni, I would have decreed that you be ostracized, but what can I do to you? You are Mischatey מִתְחַטֵּא with God and He does your bidding, like a son who is Mischatey מִתְחַטֵּא with his father and his father does his bidding without reprimand. After all, rain fell as you requested. About you, the verse states: “Let your father and your mother be glad, and let she who bore you rejoice” (Proverbs 23:25).

What does this phrase, Mischatey מִתְחַטֵּא mean?  It does not mean, literally to sin.  A closer definition is to bother or toy with God, as a small child who makes various demands and kind of exasperates his parent. Because he is so cute and endearing, the parent does not become annoyed but rather indulges him.

We get that idea contextually from how the Gemara on 23b elaborates on the story:

Like a son who nags his father and his father does his bidding. And the son says to his father: Father, take me to be bathed in hot water; wash me with cold water; give me nuts, almonds, peaches, and pomegranates. And his father gives it to him.

Rashi here on 19a uses an old French word, forfeis [forfais], which in Otzar Loazey Rashi is translated as to misbehave.

The word “Chet” itself is etymologically from to stray off the mark.  See Machberes Menachem “Chet”, and Judges 20:16.  Rambam and Bartenura Mishnah Taanis 3:8 translate it as To delight and be indulged.  Rashi in Menachos (66b) translates it as a child’s meandering and indulgence. All of this adds up to the idea that somehow, even though the request is inappropriate and immature, the prayer is indulged. Perhaps as it were, we can translate it as bothering God and literally “dreying him a Kup” which means to spin one’s head around with juvenile nonsense.

Midrash Tanchum (Ki Savo 1 and also VeYera 9) uses this same language in regard to prayers after the first fruit are brought. Somehow, at that auspicious time, the Jewish people are in a position to pray, and their requests will be granted even for indulgences.

Aside from just saying he was a tzaddik, how did Choni accomplish this?  Maaseh Rokeach on this mishna offers a kabbalistic idea that he invoked the ineffable name, and uniting “father” and “mother” forces, mercy and judgement in his favor to bring rain. (We already saw in Psychology of the Daf 2 that rain involves the invocation of mercy and din.)  Proof to this peshat is hinted at in Shimon ben Shetach’s answer when he quotes the verse: ““Let your father and your mother be glad” (Proverbs 23:25).”

However, I would like to offer a different reason why Choni’s prayers were accepted, which rings true to me, based on the word כבן מתחטא

There is this concept in prayer, that one should pray as an innocent child, without any sophistication or guile.  There is a responsa of the great kabbalist, Rav Shlomo Luria (98) (https://wiki.jewishbooks.org.il/mediawiki/wiki/%D7%A9%D7%95%22%D7%AA_%D7%9E%D7%94%D7%A8%D7%A9%22%D7%9C/%D7%A6%D7%97 also found in Mishna Berura 98:1 which discusses this idea.

The Maharshal was responding to someone who had a halakhic question about whether to follow a practice based on halakah or based on a kabbalistic tradition.  While he weighs and measures the validity of the practice he notes that the great Kabbalist, Rabbi Shimshon MiKinnin began to pray as a day-old infant AFTER studying the esoteric secrets of kabbalah.

His point was that simple prayer, without any mystical kavvanos, is the most powerful tool.  The mystical secrets are good for inspiration BEFORE the prayer not during prayer.  I think that was Choni’s secret weapon that confounded Shimon ben Shetach, his prayer was so simple and basic that God related to him as a small child, and could do nothing but indulge him.