Why is Viduy Maasros called a viduy when we aren’t confessing to any wrongdoing?
Chazal teach us that on Rosh Hashanah we are judged collectively and individually. How is that possible?
… I have removed all sacred shares from my home; I have given [the suitable shares] to the Levi, the orphan and widow, in accordance with all the precepts that You commanded us. I have not transgressed your commands nor have I forgotten anything. I have not consumed of it [the second maaser-tithe;] while in mourning, I have not apportioned / consumed any of it while tamei-halachically impure; nor have I used any for the dead, I have paid attention to the Voice of HaShem my Elokim and have acted in harmony with all that You commanded me.
—Devarim 26:13,14
Hashkifah-Look down; from your holy meon– habitation; in heaven and bless Your people Israel, and the soil that You have given us, the land streaming milk and honey, as You swore to our forefathers.
—Ibid 15
And the men arose from there, and they looked down upon Sodom …
—Bereishis 18:16
and they looked down: Wherever the word הַש×ְקָפָה =hashkafah is found in TeNaKâ€h, it indicates misfortune, except (Devarim 26:15) “Look down (הַש×ְקִיפָה) from your holy meon,†for the power of gifts to the poor is so great that it transforms the Divine attribute of Wrath to Mercy.
—Rashi ibid from Midrash Tanchuma Ki Sisa 14
Divine Judgment is passed on the world at four intervals [annually] … On Rosh Hashanah all those who’ve come into the world pass before Him like children of Maron i.e. single-file, individually
— Mishnah Rosh Hashanah 16A
And [please] do not put Your slave on trial; for before You [under Your exacting judgment] no living being will be vindicated.
—Tehillim 143:2
Who can say: “I have made my heart meritorious; I have purified myself from my sin�
—Mishlei 20:9
Rabbah bar Bar Chanah said in the name of Rav Yochanan: [All the same on Rosh Hashanah] they are all viewed [together] with a single [all-encompassing] look. Rav Nachman bar Yitzchok said: We also have learned the same idea: “[From the place of His habitation He looks השגיח upon all the inhabitants of the earth.] He that inventively designed the hearts of them all, Who comprehends all their doings†(Tehillim 33:14,15). … what it means is this: The Creator sees their hearts all-together and considers all their doings[collectively].
— Gemara Rosh Hashanah 18A
The revealed facet of this teaching of the sages is self-evident but the esoteric meaning is undoubtedly difficult to grasp
—Rambams commentary to Mishnah ibid
Rabi Yochonan taught “tithe so that you grow wealthy.â€
—Taanis 8B
The pauper speaks pleadingly; but the affluent respond impudently.
—Mishlei 18:23
 The juxtaposition of the Yamim Nora’im-days of Awe; and Parashas Ki Savo, almost always read a mere two weeks before Rosh Hashanah, is among the oddest vagaries of the Torah calendar. Whereas the month of Elul, the yemei Selichos and Yamim Noraim are characterized by detailed A-Z confessionals the “viduy†maasros-“confession†of proper tithing; that we find in Parashas Ki Savo seems to be anything but a confessional. While the Sforno and other commentaries search for a subtextual sin being alluded to; on the surface it reads like a kind of turned-on-its-head anti-confessional informed by an apparently unseemly braggadocio.
In it the “confessor†does not own up to any wrongdoing at all. On the contrary — he spells out all of the righteous and law-abiding things that he has done vis-à -vis the tithing of his agricultural produce. If this braggarts confessional were not enough the cocky confessor concludes his Divine conversation with a crude, insistent, strong-armed demand; boldly inviting Divine scrutiny and reeking of tit for tat: “Hashkifah … and bless Your people Israel, and the soil that You have given us … as You swore to our forefathers.†It’s almost as if the confessor was kivyachol-so to speak; challenging HaShem by insisting “I’ve done mine, now You do Yours!â€
We know that on the yemei hadin-judgment days; of Rosh Hashanah and Yom Kippur the Divine Judgment proceeds along two, seemingly mutually exclusive tracks; the individual and the collective. On the one hand the mishnah teaches that on Rosh Hashanah, like sheep passing beneath the shepherds crook for exclusive inspection, all pass before G-d single-file, kivyachol, to be judged individually. But on the other hand the gemara, teaches that on Rosh Hashanah all are viewed and judged collectively with a single all-encompassing look. According to the Lubliner Kohen, the gemara was, so to speak, apprehensive of the awesome and awful implications of trying to survive such a withering examination and, so, it diluted “sweetened†absolute justice with the less demanding single, all-encompassing look. The Rambams comment that “the esoteric meaning of this mishnah is undoubtedly difficult to grasp†is interpreted by one of the great 20th century Jewish thinkers to mean that judging collectively and individually simultaneously are two antithetical elements in one process. It seems impossible that they could coexist.
That said, being judged as a member of a large collective is the safer of the two tracks and lends itself to greater optimism for a positive outcome for the defendants. As the Izhbitzer explains; HaShem judgmental scrutiny is infinite in its scope and breadth and plumbs the infinitesimal in its attention to detail. Whenever He focuses on a single individual that individual is gripped by terror, for no individual can face G-d and declare that s/he is completely righteous and totally free of sin. One on trial by G-d can only exhale and begin to relax a bit when s/he is part of a communal body and when it is that collective entity, rather than its individual component parts, that is being judged. In a collective the component parts “clarify†one another for every soul is outstanding and pure in one specialized field. Or, as the Lubliner Kohen puts it, component parts of the whole are complimentary. What one lacks another completes … and vice versa.