Vayishlach, 36:12, 36:22--Achos Lohton Timna. Why didn’t the Ovos accept Timna’s geirus?

See Sanhedrin 99b, where the Gemara explains that Timna went to Avrohom, Yitzchok, and Ya’akov to become a giyores, to convert to Judaism, and they refused her. So she went and became Eliphaz’s concubine just to be close to the family of Avrohom Avinu, even though it was shocking for a daughter of a king to become a concubine. The Gemora then says that we were punished for this, in that Amolek descended from her union with Eliphaz. With this the gemora illustrates that what may seem to be a posuk with no special significance is actually very meaningful. But it is important to realize that this Gemora opens the window on a very significant issue.

The Alter from Slobodkeh (in his sefer Ohr Hatzafun) says that we know that Avrohom was a great seeker of geirim, and if he refused her, he must have seen terrible character traits in her.

If so, we can say that they refused her because they correctly discerned in her the midos that ultimately expressed themselves in her descendant, Amalek, and they didn’t want those personality traits grafted onto Klal Yisroel.

Even though this rejection resulted in the birth of Amoleik, it is better to allow the creation of an eternal existential threat rather than jeopardize our defining Jewish traits. Better an external threat than an dilution of our defining traits. Better to create an Amoleik than to bring middos ro’os into Klal Yisroeil.

(I wonder where those people who stick those pakeshvillen all over Yerusholayim come from. They certainly don’t exhibit the rachmonim bayshonim v’gomlei chasodim traits we are supposed to all have inherited. Of course, they are doing it l’sheim shomayim, and even rishonim use strong expressions against other rishonim they disagree with on psak and hashkofoh. But one difference is that the rishonim knew kol hatoroh kulloh, and could confidently say their shittos were daas Torah, whereas these people are using religious impetuosity to vent their achzorius. Another difference is that the pakeshvillen are often profane, arrogant, and ignorant.)

Similarly, we find the issur of accepting Amoni and Mo’avi, apparently for their bad middos. But maybe that is only after their nation had expressed the bad middoh in a mayseh which deserved punishment--shelo kidmu. Here, her middos ro’os had not yet expressed themselves.) Even so, the Torah shows us that he and the other avos should have helped her. Their refusal shows how serious a refusal to do a chesed is--our terrible nemesis Amalek came from her.

And this is the same taineh on Ya’akov for hiding Dinah from Eisav, and of course he was punished for that as well, when Dinah was taken by Shchem.

Perhaps (see Yalkut Lekach Tov at the end of Vayishlach) the taineh was not that they didn’t do differently, but that he didn’t feel any sympathy for her when they decided that they couldn’t help her. But the fact is the gemora uses the expression Lamos (in Iyov, from the shoresh “nomeis”, meaning melt, here meaning a person who shrinks from doing chesed for his neighbor) mei’rei’aihu chesed regarding Ya’akov, which sounds like a tainah for not doing differently.

Also remember what R’ Chaim Shmeulevitz says about “ohr vechoshech mishtamshim be’irbuvia” on the Makkas Choshech. Perhaps the problem in this marriage was not only the choshech alone, but the fact that it was combined with an ohr that both Eliphaz and Timna had. In other words, Timnoh was honestly motivated to become a giyores, but along with that ohr there was a choshech that they were unable to eliminate, which, in combination with their ohr, was capable of generating a terrible force.

But there might be a theme about refusing geirim, because not only do we have the Gemora in Sanhedrin about Timno, there’s also the Gemora in Sottah 42b about Orpoh, which says that both Golyas and Yishbi (who almost killed Dovid in a later battle) were among the four sons of Orpoh. The Gemora there says that omar Hakodosh Boruch Hu yovo’u b’nei haneshukoh v’yiplu b’yad bnei hadvukoh, so you can’t really tell whether there’s any taineh on No’omi for discouraging Orpoh, or the only point of the Gemora is that Orpoh was unfit to become a Jew, as shown by the sons she ultimately had. So, although there is a clear similarity between the cases of Timnoh and Orpoh– both being turned away, both giving birth to children who threatened our existence– and there’s also the Gemora about Yaakov refusing to give Dinah as a wife to Eisov, and the story of Shchem that followed, there’s no clear evidence as to how the three fit together, whether there is a general theme or mussor haskeil, or that you have to judge them on a case by case basis.

Also note that the Gemora in Yevomos (79a) says that the reason Hashem agreed to the demand of the Giv’onim to have the children of Sho’ul killed, was in order to make a Kiddush Hashem so that other potential Gerim would see the concern that the Jews have for the well-being of Gerim, and the Giv’onim lost their livelihood with the destruction of Nov. Now, Chazal also say that Yishbi’s ability to almost kill Dovid was because the aveiroh of Nov had as of then not been forgiven (that’s why he’s called Yishbi B’nov). So you have the son of a refused geir becoming the instrument of nekomoh for an injury to geirim– not good geirim, Giv’onim, but geirim nonetheless. So you see once again that Chazal stress the importance of sympathy with, and the risks of indifference to, the geir.

R’ Chaim Ehrman attended R Schwab’s chumosh shiur for four years, and in 1961 he heard the following from him:
When nations wage war, one nation generally covets the resources or the land of the other nation. Amalek went to the desert to wage war against Yisrael. Did they want the desert? There are miles and miles of desert available to any nation. There is no need to wage war to claim the desert. Amalek had a goal in mind. He wanted to show that the Am Hashem, the nation that Hashem chose to be His people are vulnerable and can be attacked like any other nation. Amalek deliberately waged war against the Will of Hashem. He wanted to show that Hashem’s nation is made up of mere humans and can lose a war (which happened when Moshe lowered his hands) like any other nation. What is the source of this hatred?

Rav Schwab answers this question based on the Gemora in Sanhedrin 99b. Amalek’s hatred came from his mother, Timna. She was a princess from the land of Canaan. She could have lead a life of luxury and royalty. She decided to become a giyores and marry into the descendants of Avraham Avinu. She approached Yaakov Avinu, but he replied, saying “you are from Canaan, and we may have nothing to do with Canaanites.” She went to Eisav, who told her that he had three wives and could not take another wife. She approached the children of Eisav and again she was rejected. Finally, Elifaz, the son of Eisav, took her as a concubine, not as a regular wife.

Timna felt totally rejected. She stooped from being a princess to a mere concubine, not even receiving a kesuba, a dowry. She realized that Hashem is the true G-d, but became very bitter because of her treatment and the respect she should have received. (Notice the warm reception Boaz gave Ruth, a princess of Moav who gave up her religion to become a giyores.) Amalek, her son, picked up the bitterness and unhappiness of Timna. He, then, decided to avenge his mother’s sadness and rejection. The mussar haskell (moral lesson to be learned) is that we must try to be mekarev (bring close) everyone, to the best of our ability, and avoid rejecting any person from Avodas Hashem.
(End Ehrman. He says that he is in middle of putting a together a sefer of the shiurim he heard from R Schwab, which will include this.)

So, you have a pretty clear difference of opinion between the Alter and R Schwab. One said that we pushed her away because she had middos m’gunos, the other says she had middos m’gunos because we pushed her away, which seems closer to what the Gemora in Sanhedrin says. Unless pshat is that we shouldn’t have pushed her away (at all, so brusquely, so completely) despite her middos m’gunos.

If I were around when Chazal talked about discouraging potential geirim, I would have asked, but look what happened when we did that to Timnoh and to Orpoh. What would they have answered? That the richuk there was too strong? That the richuk is only a test for sincerity, but once you find sincerity you should encourage them? That we were m’racheik them because of their bad middos, and better a bad goy than a bad Jew? That instead of rejecting them completely, we should have worked with them and helped them eliminate the middos ro’os and then taken them as geirim? That even if you are m’racheik, you should be close to them socially and try to do chesed for them?

At a conference in Eretz Yisroel in July 2006 about standards in Geirus, Harav Reuven Feinstein said a new pshat in Koshim Geirim L’Yisroel K’sapachas: he said that this is also referring to the punishment for being m’racheik a geir tzedek, or in making him wait five years before his geirus, because it says “m’kablim osso miyad.”

UPDATE DECEMBER 2014
I just saw Rav Bergman in his Shaarei Ora II on this parsha, and his discussion of this sugya is beautiful.  He goes with the Alter's approach.  He adds that it was davka because she was such a great person that her middos ra'os were indelible.  A normal geir will be mevatel themselves to Klal Yisrael, and overcome their natural techunos hanefesh.  But she was so great that she couldn't be mevatel herself to our hashkafos and middos, and her terrible middos would remain part of her.  But, he says, no matter what the reason is, rejecting a person who wants to become a ger has a terrible price.  He says that we see what Avraham Avinu was willing to forego, kabalas pnei haShechina, for all the years Lot was with him, so he could be mekareiv him.  He adds something I also once said: why is גדולה הכנסת אורחים מקבלת פני השכינה?  Because receiving guests is being domeh to Hashem, mah hu.... and become Godly is far greater than being in the presence of Godliness.  In any case, the idea is that kiruv is so precious and valuable that even in those cases where kiruv is not good, where it is dangerous, rejecting it causes tremendous damage.