(a) The verse in Koheles (9:11) says, "Again I saw under the sun that the race is not won by the light-footed, and that the war is not won by the strong, and also that bread does not come to the wise, and also that wealth does not come to the intelligent, and also that favor does not come to the learned, for time and death occur to all of them."

Shlomo ha'Melech is teaching us a moral lesson: Even though, from our perspective, it seems like it is usually the strong who win wars, and the wise who are able to provide themselves with sustenance, and it is usually the intelligent who become wealthy, the truth is that winning wars and gaining sustenance and becoming wealthy are not dependent on these respective features of the person. Rather, it is Hash-m Who grants success, based on His own reasons.

This implies that, from our perspective, it is the wise who become wealthy (b'Derech ha'Teva), for that is why Shlomo ha'Melech needs to teach us not to think that wealth is dependent upon wisdom. Rebbi Yehoshua ben Levi in our Gemara is telling us what is evident from our perspective. (See also EINAYIM LA'MISHPAT here.)

Of course, our Gemara is referring to Tefilah, and it is Tefilah that is the most effective way of arousing Hash-m's mercy to grant a person his desires (see Nidah 70b). Rebbi Yehoshua ben Levi, thus, is telling us to Daven for wisdom, and just as Hash-m grants wisdom, He will also grant wealth.

(b) When she told Rav Sheshes, "See...," it was meant to be understood in the figurative sense, like "Ta Chazi" means "think about this" (or as a person might say, "I see," to express that he understands something.)

(c) The Midrash (Shir ha'Shirim Rabah end of 1:1; see also beginning of Koheles Rabah and Yalkut Shimoni 2:179) records a Machlokes whether Shlomo wrote Shir ha'Shirim before of after Mishlei. All agree, though, that Koheles was written last - unlike what Rashi here implies. The OHEL MOSHE explains that Rashi here inferred from the fact that the Tana mentions Shir ha'Shirim after Mishlei and Koheles that this Tana holds Shir ha'Shirim was written last, unlike the above-mentioned Midrashim. (Note, however, that the Midrash there actually lists the three Sefarim in the exact same order as our Gemara, and immediately afterwards asks "Which of the three were written first?" It would seem that the order was chosen for another reason, unrelated to the order in which they were written - see what I wrote below, from the Rashash, regarding Sifrei Chochmah.)

The RASHASH writes that perhaps even Rashi admits that Koheles was written last. What Rashi wants to emphasize is that Shlomo wrote Shir ha'Shirim after Mishlei (but before Koheles). The reason why the Tana lists Koheles before Shir ha'Shirim is in order to list it together with Mishlei, since both Mishlei and Koheles are Sifrei Chochmah, books that teach us wisdom - which is what Rashi points out in his previous comment. (The Rashash, too, is assuming that at least with regard to Mishlei and Shir ha'Shirim, the order in which these books are listed in the Beraisa is the order in which they were written - which is not consistent with the words of the Midrash, as I noted above. In addition, his words do not explain why Rashi emphasized that Shir ha'Shirim was written "in [Shlomo's] old age , as opposed to any other time after the composition of Mishlei.)

I suspect that Rashi had something else in mind. The Gemara here (15a) tells us that "Chizkiyah and his associates wrote Mishlei, Shir ha'Shirim and Koheles...." Yet it is clear from the verses that these books were written by Shlomo! Rashi (top of 15a) explains that the verse in Mishlei 25:1 indeed states that "the men of Chizkiyah" recorded in writing the book of Mishlei, which Shlomo taught. But what about Koheles and Shir ha'Shirim?

Rashi earlier (15a DH Kesavo Yeshayah) writes that "all of the prophets wrote their books near the time of their death." Based on this, he explains why Yeshayah's prophecy was recorded by the men of Chizkiyah and not by Yeshayah himself (as the Gemara here states). Since Yeshayah died suddenly, he did not get a chance to record his prophecy in writing and other prophets had to record his prophecy for him.

If we see that the same "men of Chizkiyah" finished off the work of Shlomo (at least with regard to Mishlei), we can infer that he, too, died earlier than he had expected and did not have a chance to record his prophecies. That is why the Gemara assumes that the men of Chizkiyah also recorded the rest of Shlomo's prophecies.

However, the logic that Rashi suggests by Yeshayah would not seem to apply to the Sefarim of Shlomo. The reason Yes. and others wrote their prophecies close to their deaths is because they were recording life history and it would not be appropriate. to have many partial versions circulating if they would write up the history while it was unfolding. However Shlomo had three finished products of prophecy that were independent and would not be added to. As soon as he finished each, he should have recorded it. An alternate explanation must be given for Shlomo would have recorded his prophecies only at the end of his life. The reason may be because he only experienced these prophecies close to his death. He did not have a chance to record them and so Chizkiyah recorded them.

With regard to Koheles, it is easy to see that these are the words of an old experienced man as the Medrash writes (ibid). But was Shir ha'Shirim said by Shlomo in his old age? This is counterintuitive, since - as the Midrash in beginning of Shir ha'Shirim Rabah notes - the words of Shir ha'Shirim seem to be those of a youthful lover. However, one Midrash (Shir ha'Shirim Rabah ibid., Yalkut Shimoni 2:172) indeed records a (third) opinion that maintains Shlomo wrote all three Sefarim at approximately the same time, "close to his passing." Rashi, then, is emphasizing that according to our Gemara, even Shir ha'Shirim was said by Shlomo close to his death, and that is why it was only recorded later, by the men of Chizkiyah!

Best wishes,

Mordecai Kornfeld

I understood that the reason he was criticized for "making his mother crazy" was because she had to use such desperate tactics to get him to agree to remove the "Ayin Hara." Expressing herself in such an explicit way is also an act of desperation.

Rabeinu Gershom does explain, though (as you seem to have understood) that she removed her shirt. The Gemara may still be understood as I explained. The mother of an Amora obviously would not disrobe in front of any seeing person; she was alone with Rav Sheshes. In order to let Rav Sheshes know how desperate she was, she hinted to him, while telling him to consider that she nursed him, that she was revealing herself as she spoke. (She hinted to this by saying "these", implying that they were visible, as Rashi writes many times in the Chumash, see Rashi Shemos 15:2.) Even though nobody saw her, this is called "making his mother crazy," since it is prohibited to reveal covered parts even when in closed rooms when not absolutely necessary, as the Shulchan Aruch rules (OC 2:2).

M. Kornfeld