"Woe to the wicked, it shall be ill"
This section opens by stating that all wicked men are sad and that they say, "Woe." The wicked, as Rabbi Yitzchak points out, are those who spill their "semen in vain." Those who do this are called ra (evil), and it is the worst transgression. They never escape from Gehenom. Rabbi Yehuda further adds that it is the only sin for which one cannot atone.
The entire physical world is a shadow, a reflection of the Upper World. Everything on this physical plane has a corresponding counterpart in the supernal realm. Semen is the substance most reflective of the Light of The Creator. Hence, as raw naked energy must be concealed in high voltage cables in order to harness its power, semen must remain concealed in this physical world. When it is wasted in vain, through selfish gratification, and not used for the divine purpose of creating life and/or sharing pleasure with one's spouse, negative forces that dwell among us are free to use this energy for destructive purposes. This passage helps us cleanse sexual iniquities from the world and gives us the strength to direct our urges in a positive and sharing way.
190. If he be evil, a herald announces him in Gehenom for thirty days. All the wicked men are sad and open AND SAY, 'Woe.' For a new Judgment is awakened because of a certain person, and numerous accusers await him to welcome him AND SAY TO HIM, 'Woe.' Woe unto the wicked, woe unto his neighbor.
190. וְאִי חַיָּיבָא הוּא, כָּרוֹזָא קָרֵי עֲלֵיהּ בַּגֵּיהִנֹּם תְּלָתִין יוֹמִין, וְכֻלְּהוּ חַיָּיבַיָא, כֻּלְּהוּ עֲצִיבִין.
191. They all open and say, "Woe to the wicked, it shall be ill with him, for according to the deserving of his hands shall be done to him" (Yeshayah 3:11). What is "the deserving of his hands?" Rabbi Yitzchak said, It includes him who defiles with his hands by spilling his semen in vain.
191. כֻּלְּהוּ פָּתְחִין וַוי, דְּהָא דִינָא חַדְתָּא אִתְעַר הַשְׁתָּא, בְּגִינֵיהּ דִּפְלַנְיָא כַּמָּה גַרְדִינִין דְּנִמּוּסִין מִזְדַּמְּנִין לְקִבְלֵיהּ, וּלְאַקְדָּמָא לֵיהּ וַוי, אוֹי לָרָשָׁע אוֹי לִשְׁכֵנוֹ, וְכֻלְּהוּ פָּתְחִין וְאָמְרִין, אוֹי לְרָשָׁע רָע כִּי גְמוּל יָדָיו יֵעָשֶׂה לוֹ. מַאי גְּמוּל יָדָיו. אֲמַר ר' יִצְחָק. לְאַכְלָלָא, מַאן דְּזָנֵי בִּידוֹי, לַאֲפָקָא וּלְחַבְּלָא זַרְעֵיהּ בְּרֵיקַנְיָא.
192. For we have learned that he who spills his semen in vain is called evil (Heb. ra), and cannot behold the face of the Shechinah, as it is written, "For You are not an El that has pleasure in wickedness, nor shall evil dwell with You" (Tehilim 5:5) and also "And Er, Yehuda's firstborn, was evil (Heb. ra)" (Beresheet 38:7). Here too, "Woe to the wicked...ill (Heb. ra)" ALLUDES TO HIM WHO SPILLS HIS SEMEN IN VAIN. Woe to the wicked who is evil and made himself evil (Heb. ra), "for according to the deserving of his hands shall be done to him." This means that whoever whores himself by letting his semen spill in vain is punished in the world of truth more than any OTHER TRANSGRESSION.
192. דְּהָא תָּנִינָן, כָּל מַאן דְּאַפֵּיק זַרְעֵיהּ בְּרֵיקַנְיָא, אִקְרֵי רָע, וְלָא חָמֵי אַפֵּי שְׁכִינְתָּא, דִּכְתִיב כִּי לֹא אֵל חָפֵץ רֶשַׁע אַתָּה לֹא יְגוּרְךָ רָע, וּכְתִיב וַיְהִי עֵר בְּכוֹר יְהוּדָה רַע, אוֹף הָכָא, אוֹי לְרָשָׁע רָע, וַוי לְהַהוּא חַיָּיבָא דְּאִיהוּ רַע, דַּעֲבַד גַּרְמֵיהּ רַע, כִּי גְמוּל יָדָיו יֵעָשֶׂה לוֹ, לְאַכְלָלָא, מַאן דְּזָנֵי בִּידוֹי, לַאֲפָקָא וּלְחַבְּלָא זַרְעֵיהּ בְרֵיקַנְיָא, וּלְהַאי טָרְדִין בְּהַהוּא עַלְמָא יַתִּיר מִכֹּלָּא.
193. Come and see it is written, "Woe to the wicked." Since it says, "Woe to the wicked (Heb. rasha)," why add 'evil (ra)' SEEING THAT THE WICKED IS EVIL? This is as I said, that he has made himself evil, ESPECIALLY HE WHO SPILLED HIS SEMEN IN VAIN. ALSO: " ...Nor shall evil dwell with You." Everyone ascends FROM GEHENOM save this one, who does not. HE ASKS, Would you say that other evil - doers who killed people ARE BETTER THAN HE, AND WILL ASCEND WHILE HE SHALL NOT? HE ANSWERS, Come and behold, everyone rises but he does not, because they killed other people, yet he killed his own children, and spilled much blood. Come and behold, it is not written of any other wicked man in the world that he "displeased Hashem" (Beresheet 38:10), only in this case where it says, "And the thing which he did displeased Hashem." Why? Because, the verse says, "He spilled it on the ground" (Ibid. 9).
193. תָּא חֲזֵי, דְּהָא כְתִיב אוֹי לְרָשָׁע, כֵּיוָן דִּכְתִיב אוֹי לְרָשָׁע, אַמַּאי רָע. אֶלָא כְּמָה דַּאֲמִינָא, דַּעֲבַד גַּרְמֵיהּ רָע. וּכְתִיב לֹא יְגוּרְךָ רָע. וְכֻלְּהוּ סָלְקִין, וְהַאי לָא סָלֵיק, וְאִי תֵימָא שְׁאָר חַיָּיבִין דְּקָטְלוּ בְּנֵי נָשָׁא. תָּא חֲזֵי, כֻּלְּהוּ סָלְקִין, וְהוּא לָא סָלֵיק, מ"ט, אִינוּן קְטִילוּ בְּנֵי נָשָׁא אָחֳרָא, וְהַאי קָטֵיל בְּנוֹי מַמָּשׁ, אוֹשִׁיד דָּמִין סַגִּיאִין. תָּא חֲזֵי, בִּשְׁאָר חַיָּיבֵי עַלְמָא, לָא כְתִיב וַיֵּרַע בְּעֵינֵי ה,' וְכָאן כְּתִיב, וַיֵּרַע בְּעֵינֵי ה' אֲשֶׁר עָשָׂה. מ"ט, מִשּׁוּם דִּכְתִיב וְשִׁחֵת אַרְצָה.
194. We learned that Rabbi Yehuda said, There is no sin in the world that one cannot repent, other than the one OF SPILLING ONE'S SEMEN IN VAIN. There are no wicked men who shall not behold the face of the Shechinah IN THEIR DEATH, save him of whom it says "nor shall evil dwell with You" at all. Rabbi Yitzchak said, Happy are the righteous in this world and in the World to Come, of whom scripture says, "Your people also shall be all righteous, they shall inherit the land forever" (Yeshayah 60:21). Rabbi Yehuda said, It is also said in "I will walk before Hashem in the land of the living" (Tehilim 116:9), WHICH IS THE SHECHINAH, CALLED LAND; THE LAND HERE ALLUDES TO THE SHECHINAH.
194. תְּנַן, אֲמַר ר' יְהוּדָה, לֵית לָךְ חוֹבָא בְּעַלְמָא דְּלָא אִית לֵיהּ תְּשׁוּבָה, בַּר מֵהַאי, וְלֵית לָךְ חַיָּיבַיָא דְּלָא חָמָאן אַפֵּי שְׁכִינְתָּא, בַּר מֵהַאי, דִּכְתִיב לֹא יְגוּרְךָ רָע כְּלַל. א"ר יִצְחָק, זַכָּאִין אִינוּן צַדִּיקַיָיא, בְּעַלְמָא דֵין, וּבְעַלְמָא דְאָתֵי, עֲלַיְיהוּ כְתִיב, וְעַמֵּךְ כֻּלָּם צַדִּיקִים לְעוֹלָם יִירְשׁוּ אָרֶץ. מַאי לְעוֹלָם יִירְשׁוּ אָרֶץ, א"ר יְהוּדָה, כְּמָה דִכְתִיב אֶתְהַלֵּךְ לִפְנֵי ה' בְּאַרְצוֹת הַחַיִּים.
195. "And Jacob lived" (Beresheet 47:28) among them: Another explanation for this is that a man should not mingle his image with that of the idolatrous nations, for the one is holy and the other defiled.
195. וַיְחִי יַעֲקֹב בְּגַוַּיְיהוּ. ע"ד לִבָּעֵי לֵיהּ לְבַר נָשׁ דְּלָא לְאִתְעַרְבָא צוּלְמָא דִילֵיהּ בְּצוּלְמָא דְעכו"ם, בְּגִין דְּהַאי קַדִּישָׁא, וְהַאי מְסָאֲבָא.