(a) Moshe Rabeinu's intention was to clarify the purpose of the rebuke of
Parshas Bechukosai. He "blessed with eight letters" in order to point out
that these blessings were the *result* of the curses that incorporated those
letters in Bechukosai. That is, the purpose of the Tochechah was not to
punish the Jewish people, but rather to turn them in the proper direction.
(See Berachos 5a, "Just as salt sweetens the meat, so, too, the afflictions
described in the Tochechah cleanse a person's sins," and Chagigah 9b,
"Poverty is as appropriate for Yisrael as red reins for a white horse.")
It is for the same reason that Moshe Rabeinu said the Tochechah "from Vav to
Heh," and not from Alef to Tav. The MAHARSHA cites a Midrash (Vayikra Rabah
35:1) which explains that the curses in Parshas Ki Savo work backwards, from
Vav to Heh, in order to show that they will be "reversed" and made into
blessings when the Jewish people [repent and] follow the Torah. Moshe
Rabeinu was pointing out that the curses were not an end in their own right,
but a means to bringing about blessing by causing the Jewish people to
repent (see Maharsha).
What, then, does the Gemara mean when it says that we see from the Tochechah
that "the ways of man cannot compare to the ways of Hashem?"
A set of verses spanning from Alef to Tav alludes to the fact that these
verses describe a natural process, a process that progresses in an
anticipated fashion and is built into the structure of the world. As the
MESHECH CHOCHMAH writes (beginning of Bechukosai), this is the reason why
the verses of "Ashrei" (Tehilim 155) progress according to the Alef Beis;
the Psalm illustrates that Hashem built into the nature of the world that
the needs of each and every creature are provided for in a natural way
("Pose'ach Es Yadecha...," see Berachos 4b).
Likewise, the blessings of Bechukosai progress from Alef to Tav in order to
show that Hashem built into the world the mechanism that the those who
perform the will of Hashem will be blessed with plenty. This is the way the
world should naturally be.
Moshe Rabeinu, however, realized that mankind has a tendency not to live up
to Hashem's expectations. Adam ha'Rishon ate from the Etz ha'Da'as; the
Jewish people sinned with the Egel ha'Zahav after receiving the Torah. Moshe
saw that the Jewish people would attain their ultimate goal only after they
would suffer the Yisurim of "Vav to Mem." That is why his blessings were
given in the format of Vav to Mem and his curses from Vav to Heh, as we
explained above. In this sense, the expectations of man do not live up to
those of his Creator. This is the lesson learned from the Gemara's
comparison of the blessings of Moshe to those of Hashem.
(b) The MAHARSHA points out that the letters between Vav and Mem are those
that separate between Heh and Nun, the only two letters that "have no pair."
(Alef, the value of which is 1, can be paired with Tes, which equals 9, to
make a full 10, and Beis, 2, can be paired with Ches, 8, to make a full 10,
etc.; Yud, 10, can be paired with Tzadi, 90, to make a full 100, etc.
However, no single letter can be combined with Heh, 5, to make 10, or with
Nun, 50, to make 100.)
We can develop this theme further by suggesting that the two letters Heh and
Nun represent Hashem and Yisrael, the two "unique ones" (Berachos 6a). Heh
represents Hashem, as the Gemara says in Shabbos (104a), while Nun stands
for "Ne'eman," or "the man of faith" (ibid.). (Nun might also allude to the
50 "gates of wisdom" that Hashem opens to the faithful (as in Rosh Hashanah
21b), and to the value, or "Erech," that the Torah ascribes to an adult
Jewish male, in Vayikra 27:3.) As the Midrash says, a Jew has no other
"partner;" Hashem is his partner (Yalkut Shir ha'Shirim #985; see also
Bereishis Rabah 11:18, "Yisrael has no partner; Shabbos is the partner of
Yisrael").
When the Jew cleaves to his Creator, the Heh and Nun come together, making
the word "Hen," as in "*Hen* Yir'as Hashem Hi Chochmah" -- "Behold, fear of
G-d is the only true wisdom." It is when the other eight letters, from the
Vav to the Mem (which might correspond to the eight Sheratzim that spread
Tum'ah by distancing a person from Hashem; see Insights to Eruvin 13:3),
come between Heh and Nun and separate them from each other that the
Tochechah comes into effect. That is why the Tochechah was given "from Vav
to Mem," measure for measure.
When Moshe Rabeinu reversed the usage of the letters for the Tochechah, he
again started from Vav. However he did not stop at Mem, separating the Heh
from the Nun. He went on until reaching back to Heh, symbolizing that the
purpose of the Tochechah is to bring the Jewish people back to Hashem. The
Vav then joins with the letter Heh, to become a letter of Hashem's name (as
in Shabbos 104a).
According to the Yerushalmi (cited by TOSFOS in Rosh Hashanah 18a), although
the verses state that during the first Beis ha'Mikdash period, Yerushalayim
was conquered on the *ninth* of Tamuz (Yirmeyahu 39:2), in truth it was only
conquered on the seventeenth of the month (as in the times of the second
Beis ha'Mikdash). Hashem caused the prophet to "confuse the calculations"
and had him write that it occurred on the wrong date.
Perhaps the eight-day miscalculation was meant to show that the destruction
of the Beis ha'Mikdash was brought about by the "eight letters" that the
Jewish people allowed to separate between the Heh and the Nun through their
sins, bringing about the Tochechah. (M. Kornfeld)