Milah Points

The Bartenura on the Torah (17:24) says וקשה לפי זה למה המתין כל כך למול את עצמו. י"ל משום דהא דאמרינן שקיים כל המצות היינו לאחר שנמול אבל קודם לכן לא היה לו דעת לקיים מצות ולא נפתחו עיני שכלו וכדפרש"י לעיל שלא היה בו כח לסבול גלוי השכינה ולעמוד.  According to the Bartenura, Avraham fulfilled all the mitzvot only after his Milah.  The Maharsha in Yevamot (100b) suggests the same idea to explain how Avraham could marry Hagar, who was a first generation Egyptian, whom one is prohibited from marrying?  He says, it must be Avraham only kept the Torah after his Milah.  (According to the Maharsha it still is difficult how did Avraha marry  קטורה who Chazal identify as Hagar, at that point it was after Avraham's bris?)  See here where he cites Rishonim deal with the question about Hagar.   

According to the Bartenura, the bris milah of Avraham was not a mere mitzvah like any other but it was a transformation of his entire being.  This is supported from the Midrash beginning of Vaerah which comments on the greater level of Avraham after the milah.  

The Gemarah Avodah Zarah (27a) has a machlokes tanaim if Milah has to be done lishma.  The opinion of R' Yose is that it does not.  The Yaavetz asks a contradiction because in Yevamot (46b) R' Yose says if one comes before Beit Din with a milah having been done we can't just do the tevilah part because it is possible the milah was not done lishma.  But R' Yose doesn't hold a milah has to be done lishma?  The Chasam Sofer (Yoreh Deah teshuva #1,300) answers by differentiating between the milah of a yisrael and that of one who wants to be converted.  The regular mitzvah of milah for a Yisrael does not have to be one lishma but to enter into the Jewish nation one requires their milah being done lishma.  The Meshech Chachma (end of Lech Lecha and Bo) also suggests this idea as does Rav Yosef Engel. 

The possuk (17:23) says that Avraham gave all the people in his household a milah and then the last possuk in the parsha (17:27) repeats that Avraham gave them a milah.  Why does it repeat this?  The Ramban says that Avraham first gave everyone else a milah and then he gave himself a milah.  How could he give them a milah if he himself didn't have a milah (according to the opinion in Avodah Zarah that only one who has a milah can give a milah?)  The Chasam Sofer says that since Avraham was intending to get a milah he is considered to have a milah.  But that is only if he ended up getting a milah.  That's what the last possuk means, only after Avraham gave himself a milah was their milah complete (that is how it is נמלו אתו, with his bris their bris was complete as well.) 

The Tosfat Yeshanim in Yevamot asks the question of the Yaavetz and answers that R' Yose said in Avodah Zarah a milah doesn't have to be done lsihma only when a Jew is standing over the gentile telling him to do the milah lishma.  In other words, R' Yose also holds a milah has to be done lishma but it suffices it a gentile does it when a Jew tells him what to do.  This is very difficult to read into the Gemarah Avodah Zarah.  See also Achiezer volume 3 siman 27. 

The Avnei Nazer Yoreh Deah (345 end of the teshuva) takes issue with the Chasam Sofer for (if I understand his question correctly,) for if a milah not done lishma is considered a milah then the ger should be no different from someone who doesn't have an ערלה that wants to become a ger where he just does tevilah?  His question is propitiated on the assumption that there is no הטפת דם ברית in those situations which is a machlokes Rishonim.  But even if those cases don't require הטפת דם ברית here it is worse for in those scenarios the ger doesn't have an ערלה, so he just does tevilah but here the ger was an ערל and a milah no done lishma doesn't remove the ערלה status vis-a-vis gerus.  

R' Yose learns his law of milah lishma from the parsha here (17:13) הִמּ֧וֹל ׀ יִמּ֛וֹל יְלִ֥יד בֵּֽיתְךָ֖ וּמִקְנַ֣ת כַּסְפֶּ֑ךָ וְהָיְתָ֧ה בְרִיתִ֛י בִּבְשַׂרְכֶ֖ם לִבְרִ֥ית עוֹלָֽם, he learns the double verb teaches that circumcision may be performed by anyone.  However, if we put the idea of the Bartenura and the Chasam Sofer together it is difficult for this is the milah of gerus and there everyone requires it to be lishma?