This means something pretty straightforward on a peshat level, namely material reward in this world for doing good. But of course Chazal interpret it to mean something else as well. In Bava Metzia 107a, right at the bottom of the page, we have a statement by Rabbi Yochanan:
R. Johanan did not interpret thus, but: 'Blessed shalt thou be in the city' — that the privy closet shall be near to thy table, but not the synagogue. R. Johanan's interpretation is in accordance with his opinion, viz., One is rewarded for walking [to a synagogue]. 'And blessed shalt thou be in the field' — that thy estate shall be divided in three [equal] portions of cereals, Olives, and vines. 'Blessed shalt thou be when thou comest in, and blessed shalt thou be when thou goest out' — that thine exit from the world shall be as thine entry therein: just as thou enterest it without sin, so mayest thou leave it without!
This is a rather explicit statement that one enters the world without sin, in contrast to the Christian idea of the taint of original sin.
The Rashash makes a comment which is likely true: מכאן סתירה קצת לבעלי דעת הגלגול. Indeed, it seems fairly straightforward that this contradicts the belief if gilgul, because not only do they maintain that many people have had past lives, and thus don't enter the world as a tabula rasa, but they maintain that the purpose of returning to the world is to fix the flaws and sins from a past life!
Now, nothing needs to be contradictory in rabbinic literature, because harmonization is the rule. Often the harmonization is correct, but sometimes it is not, but people will explain away contradictions anyway. And I don't doubt there is a resolution to this contradiction or apparent contradiction.
Still, there is a noteworthy idea in Rashash, and that is that we can look at gemaras, read their implications, and try to deduce what Chazal's theology was. And that this theology might be at odds with present-day popular theology, even theology grounded in kabbalah and the Zohar.
Indeed, it seems likely that Chazal did not believe in gilgul. (The purported reference to Pharisees believing it, mentioned in Josephus, is most likely a reference to techiyat hameitim rather than gilgul.) And it seems likely that the belief in gilgul comes from sources foreign to Judaism, but has tainted our entire theology in ways impacting our conception of sechar veOnesh, of tzaddik vera lo, and indeed much of our purpose on this earth. It is very far-reaching.
The "problem" in saying this is that kabbalists can find many sources for their beliefs in the words of Chazal. However, is this an honest reading of sources to determine Chazal's beliefs, or is it reinterpretation of sources to say what you want them to say, in order to read your own beliefs into Chazal? This is the issue I have about much "pnimiyus" interpretation of gemara and aggada. If you don't like what a source says, say it has some hidden, deep mystical meaning. But mystics are likely not the only culprits in this regard. Rationalists are guilty of this as well. Shadal indicts boths Jewish philosophers and Jewish kabbalists for engaging in such reinterpretive derash, which reads their own values and beliefs into Chazal. And while everyone likes to cite Rambam in his introduction to perek Chelek as encouraging the metaphorical, deeper meaning of otherwise ridiculously impossible aggadot (for example, Og's incredible height, or the sun and the moon speaking), perhaps this could stem from Rambam's inability to attribute theological or scientific beliefs he would regard as extremely silly. If so, such reinterpretation, rather than careful analysis and consideration of Chazal's actual words, may lead us away from the truth of Chazal's intent.
Which brings us to a gemara we learned in daf yomi but two days ago, on Bava Metzia 105a:
We learnt elsewhere: Wild olives and grapes — Beth Shammai declare them unclean; Beth Hillel, Clean. What is meant by 'wild [perize] olives?' — Said R. Huna: Wicked olives [i.e., which yield very little oil]. R. Joseph said: And what verse [warrants this interpretation]? — Also the robbers [perize] of thy people shall exalt themselves to establish the vision; but they shall fail. R. Nahman b. Isaac said: It is from this verse: If he beget a son that is a robber [pariz] a shedder of blood.
What is peshat in the gemara? On a simple, rationalist (and I would argue, true) level, the brayta mentioned pritzei zaitim. Paritz probably means uncontrolled, and thus wild, undomesticated, uncultivated grapes. Since they are not cultivated, they don't produce much. Are they fit for eating? This might well be the source of Bet Shammai and Bet Hillel. Since Bet Shamai consider it fit for eating, they can become ritually impure. And Bet Hillel disagree.
The Amoraim know this tradition of the meaning of the Mishnaic term, but the language has changed from Tannaitic to Talmudic times. And as a mnemonic, or to demonstrate the use of this word to refer to olives and grapes of extremely low yield, different Amoraim offer different psukim. Thus, Rav Huna calls them "wicked" olives. This is idiomatic. As Rashi notes:
פריצי זיתים - כדמפרש רשעי זיתים וענבים שהן לעולם בוסר שאין בישולן נגמר לעולם
They are "wicked" in terms of not producing the good things they should produce, such that they never fully ripen. But not that they are really "wicked" and evildoers. It is ridiculous, from a rationalist perspective, to speak of wicked grapes on a literal level! Does a grape have bechirah chofshis? Are they given any mitzvos or avairos? Of course not. It must be idiomatic, and Rashi knows this well.
But what of the prooftexts, when they base this interpretation of a pasuk? There are two answers, to my mind. The first is that these pesukim are actually talking about the wicked, such that we get "reshaim" from the pasuk. And subsequently, one we have "wicked" in hand, we apply the idiom to the grapes or the olives. The alternative is that "wicked" is just an idiom which only crops up in the words of Rav Huna, but when the other Amoraim derive it, they focus on the meaning of the idiom, and thus are trying to find a message of disappointment associated with the word paritz. The two prooftexts are as follows. First, in Daniel 11:14:
|יד וּבָעִתִּים הָהֵם, רַבִּים יַעַמְדוּ עַל-מֶלֶךְ הַנֶּגֶב; וּבְנֵי פָּרִיצֵי עַמְּךָ, יִנַּשְּׂאוּ לְהַעֲמִיד חָזוֹן--וְנִכְשָׁלוּ.||14 And in those times there shall many stand up against the king of the south; also the children of the violent among thy people shall lift themselves up to establish the vision; but they shall stumble.|
I believe that it is no accident that the quote provided in the gemara extend to the end of the verse. Thus yes, it might merely serve to establish them as "the robbers" or "the children of the violent," and the context in the gemara is sufficient to tell us that these are people, and the context in the pasuk is sufficient to establish them as wicked, somehow. But if the purpose was the context up to the end of the pasuk, then the fact that they failed and thus provided a disappointing yield. The second pasuk is in Yechezkel 18:10:
|י וְהוֹלִיד בֵּן-פָּרִיץ, שֹׁפֵךְ דָּם; וְעָשָׂה אָח, מֵאַחַד מֵאֵלֶּה.||10 If he beget a son that is a robber, a shedder of blood, and that doeth to a brother any of these things,|
This (unlike the previous example) could easily be to prove that a paritz is simply no good. Alternatively, the clear context in this pasuk is a rasha ben tzadik. Thus, the tzadik begets a son whose behavior is disappointing, such that he does not live up to the standard of righteousness of his father, to say the least.
I am comfortable with either explanation, and they both work out well with the clear peshat in the gemara, that the grapes are wicked only on an idiomatic level.
But someone more mystically inclined can find an entirely different message in this gemara, reading a belief in gilgul into it. The grapes are wicked because in a past life they were humans who sinned.
Thus, as Daf Notes reports on this gemara, with a devar Torah written by Rabbi Yosef Dov Karr (see there for his full remarks):
The Ben Yehaydah explains that a wicked person can come back as a gilgul (reincarnation) as fruit and his neshamah (soul) gets a tikkun in that a person makes a blessing on this fruit. Unfortunately, there are some evil people that are so wicked that when they return as fruit, they come back as peritzim, or fruit that will never ripen. They are not even considered a food (and therefore cannot become tamei). One does not say a blessing on peritzim and the wicked person does not receive his tikkun.
But what would Beis Shammai say about these reincarnated fruits? More seriously, if (and I stress the word if) gilgul is a theological belief foreign to Judaism, besides being an untrue and silly interpretation of the gemara, and one which corrupts the words of our Sages, it also changes our concept of sechar veOnesh even further. I can understand the justice in gilgul. It just takes the long view, that a soul has multiple visits to earch to achieve perfection, and thus there is a purpose to returning to earth and undergoing certain types of suffering. But this is gilgul just for the sake of punishment. This is not punishment in gehinnom to purify it; and it is not returning to earth to fix it. Rather, stick the soul in a fruit just out of spite, and deprive it an opportunity to fix itself, at least in that lifetime. (And why call these fruits wicked and not other fruits, less wicked who can achieve a tikkun, reshaim as well?) One can formulate a satisfactory answer within the system, but it seems even more problematic, seeming to make Hashem into a vengeful God, punishing a wicked soul just for the "heck" of it, and with no toeles in the punishment.