(1) When Abram was ninety-nine years old, Adonai appeared to Abram and said to him, “I am El Shaddai. Walk in My ways and be blameless. (2) I will establish My covenant between Me and you, and I will make you exceedingly numerous.” (3) Abram threw himself on his face; and God spoke to him further, (4) “As for Me, this is My covenant with you: You shall be the father of a multitude of nations. (5) And you shall no longer be called Abram, but your name shall be Abraham, for I make you the father of a multitude of nations. (6) I will make you exceedingly fertile, and make nations of you; and kings shall come forth from you. (7) I will maintain My covenant between Me and you, and your offspring to come, as an everlasting covenant throughout the ages, to be God to you and to your offspring to come. (8) I assign the land you sojourn in to you and your offspring to come, all the land of Canaan, as an everlasting holding. I will be their God.” (9) God further said to Abraham, “As for you, you and your offspring to come throughout the ages shall keep My covenant. (10) Such shall be the covenant between Me and you and your offspring to follow which you shall keep: every male among you shall be circumcised. (11) You shall circumcise the flesh of your foreskin, and that shall be the sign of the covenant between Me and you. (12) And throughout the generations, every male among you shall be circumcised at the age of eight days. As for the homeborn slave and the one bought from an outsider who is not of your offspring, (13) they must be circumcised, homeborn, and purchased alike. Thus shall My covenant be marked in your flesh as an everlasting pact. (14) And if any male who is uncircumcised fails to circumcise the flesh of his foreskin, that person shall be cut off from his kin; he has broken My covenant.”
...וְעַל הַמִּילָה נִכְרְתוּ שְׁלֹשׁ עֶשְׂרֵה בְּרִיתוֹת עִם אַבְרָהָם אָבִינוּ. (בראשית יז ב) ״וְאֶתְּנָה בְרִיתִי בֵּינִי וּבֵינֶךָ״. (בראשית יז ד) ״אֲנִי הִנֵּה בְרִיתִי אִתָּךְ״. וַהֲקִמֹתִי אֶת בְּרִיתִי בֵּינִי וּבֵינֶךָ. לִבְרִית עוֹלָם. (בראשית יז ט) ״וְאַתָּה אֶת בְּרִיתִי תִשְׁמֹר״. (בראשית יז י) ״זֹאת בְּרִיתִי אֲשֶׁר תִּשְׁמְרוּ״. (בראשית יז יא) ״וְהָיָה לְאוֹת בְּרִית״. (בראשית יז יג) ״וְהָיְתָה בְרִיתִי בִּבְשַׂרְכֶם״. לִבְרִית עוֹלָם. (בראשית יז יד) ״אֶת בְּרִיתִי הֵפַר״. (בראשית יז יט) ״וַהֲקִמֹתִי אֶת בְּרִיתִי אִתּוֹ. לִבְרִית עוֹלָם״. (בראשית יז כא) ״וְאֶת בְּרִיתִי אָקִים אֶת יִצְחָק״:
...in connection with Circumcision, thirteen covenants were made with our ancestor Abraham: "And I will make My covenant between Me and thee" (Gen. 17:2); "As for me. behold, My covenant is with thee" (ib. 17:4); "And I will establish My covenant between Me and thee" (ib. 17:7); "for an everlasting covenant" (ib. 17:7); "And as for thee, thou shalt keep My covenant" (ib. 17:9); "This is My covenant which you shall keep" (ib. 17:10) "And it shall be a token of a covenant" (ib. 17:11); "And My covenant shall be in your flesh" (ib. 17:13); "for an everlasting covenant" (ib. 17:13); "he hath broken my covenant" (ib. 17:14); "And I will establish My covenant with him" (ib. 17:19); "for an everlasting covenant" (ib. 17:19); "But My covenant I will establish with Isaac" (ib. 17:21).
(א) וּבַיּוֹם הַשְּׁמִינִי יִמּוֹל. אֵין כְּתִיב שָׁם שֶׁיּוֹצִיא הוֹצָאוֹת עַל הַמִּילָה. בֹּא וּרְאֵה, כַּמָּה יִשְׂרָאֵל מְחַבְּבִין אֶת הַמִּצְוֹת, שֶׁהֵם מוֹצִיאִין הוֹצָאוֹת כְּדֵי לִשְׁמֹר אֶת הַמִּצְוֹת וְלִשְׂמֹחַ בָּהֶם. אָמַר הַקָּדוֹשׁ בָּרוּךְ הוּא, אַתֶּם מְשַׁמְּרִים אֶת הַמִּצְוֹת וְתִשְׂמְחוּ בָּהֶן, אֲנִי מוֹסִיף לָכֶם שִׂמְחָה, שֶׁנֶּאֱמַר: וְיָסְפוּ עֲנָוִים בַּה' שִׂמְחָה וְגוֹ' (שם כט, יט). חֲבִיבָה הַמִּילָה, שֶׁנִּשְׁבַּע הַקָּדוֹשׁ בָּרוּךְ הוּא לְאַבְרָהָם, שֶׁכָּל מִי שֶׁהוּא מָהוּל אֵינוֹ יוֹרֵד לַגֵּיהִנָּם, שֶׁנֶּאֱמַר: בַּיּוֹם הַהוּא כָּרַת ה' אֶת אַבְרָם בְּרִית לֵאמֹר (בראשית טו, יח). וּמִי יֵרֵד לְשָׁם. רְאֵה מַה כְּתִיב אַחֲרָיו, אֶת הַקֵּינִי וְאֶת הַקְּנִזִּי וְגוֹ'...
מַעֲשֶׂה שֶׁשָּׁאַל טוּרְנוּסְרוּפוּס הָרָשָׁע אֶת רַבִּי עֲקִיבָא, אֵיזוֹ מַעֲשִׂים נָאִים, שֶׁל הַקָּדוֹשׁ בָּרוּךְ הוּא אוֹ שֶׁל בָּשָׂר וָדָם. אָמַר לוֹ: שֶׁל בָּשָׂר וָדָם נָאִים. אָמַר לוֹ טוּרְנוּסְרוּפוּס, הֲרֵי הַשָּׁמַיִם וְהָאָרֶץ יָכֹל אָדָם לַעֲשׂוֹת כַּיּוֹצֵא בָּהֶם אָמַר לוֹ רַבִּי עֲקִיבָא, לֹא תֹּאמַר לִי בְּדָבָר שֶׁהוּא לְמַעְלָה מִן הַבְּרִיּוֹת שֶׁאֵין שׁוֹלְטִין עָלָיו, אֶלָּא אֱמֹר דְּבָרִים שֶׁהֵם מְצוּיִין בִּבְנֵי אָדָם. אָמַר לוֹ: לָמָּה אַתֶּם מוּלִין. אָמַר לוֹ: אֲנִי הָיִיתִי יוֹדֵעַ שֶׁעַל דָּבָר זֶה אַתָּה שׁוֹאֲלֵנִי, וּלְכָךְ הִקְדַּמְתִּי וְאָמַרְתִּי לְךָ, שֶׁמַּעֲשֵׂה בְּנֵי אָדָם נָאִים מִשֶּׁל הַקָּדוֹשׁ בָּרוּךְ הוּא. הֵבִיא לוֹ רַבִּי עֲקִיבָא שִׁבֳּלִים וּגְלֻסְקָאוֹת, אָמַר לוֹ: אֵלּוּ מַעֲשֶׂה הַקָּדוֹשׁ בָּרוּךְ הוּא, וְאֵלּוּ מַעֲשֶׂה יְדֵי אָדָם. אָמַר לוֹ: אֵין אֵלּוּ נָאִים יוֹתֵר מִן הַשִּׁבֳּלִים אָמַר לוֹ טוּרְנוּסְרוּפוּס, אִם הוּא חָפֵץ בַּמִּילָה, לָמָּה אֵינוֹ יוֹצֵא הַוָּלָד מָהוּל מִמְּעֵי אִמּוֹ. אָמַר לוֹ רַבִּי עֲקִיבָא, וְלָמָּה שׁוֹרְרוֹ יוֹצֵא עִמּוֹ וְהוּא תָּלוּי בְּבִטְנוֹ וְאִמּוֹ חוֹתְכוֹ וּמַה שֶׁאַתָּה אוֹמֵר לָמָּה אֵינוֹ יוֹצֵא מָהוּל, לְפִי שֶׁלֹּא נָתַן הַקָּדוֹשׁ בָּרוּךְ הוּא אֶת הַמִּצְוֹת לְיִשְׂרָאֵל אֶלָּא לְצָרֵף אוֹתָם בָּהֶם. וּלְכָךְ אָמַר דָּוִד, אִמְרַת ה' צְרוּפָה (תהלים יח, לא).
(1) And on the eigth day you shall circumcise It doesn't say here to make parties about the circumcision. Come and see how much Israel loves the commandments, that they make parties in order to observe the commandments and to have joy in them. The Holy One, Blessed is He says "you guard the commandments and celebrate them, I will increase joy for you", as it says (Isaiah 29:19) "The humble also shall increase their joy in the LORD..." [Beloved is circumcision, for The Holy One Blessed is He swore to Abraham that all who are circumcised will not descend to Gehenom, as it says (Genesis 15:18) "In that day the LORD made a covenant with Abram, saying...", and who descended to there? See what is says next (Genesis 15:19) "the Kenite, and the Kenizzite..."
It once happened that the evil Turnus Rufus asked Rabbi Akiva, "which are the greater works, those of the Holy One Blessed is He or those of flesh and blood?" He said to him, "Those of flesh and blood are greater." Turnus Rufus said, "But the Heavens and Earth — is Man able to make such as those?" Rabbi Akiva said to him, "Don't speak to me about something which is beyond Man, which he has no mastery over, rather speak of things which are found among people." He said, "Why do you circumcise?" He replied, "I knew you were going to ask me about that, which is why I started by telling you that the works of Man are better than the works of the Holy One Blessed is He." Rabbi Akiva brought him stalks [of grain] and loaves [of bread]. He said to him, "These are the works of the Holy One Blessed is He, and these are the works of Man." He said, "Aren't these better than the stalks?!' Turnus Rufus [then] said to him, "If He wants circumcision, why does the infant not emerge circumcised from his mother's womb?" Rabbi Akiva said to him ,"And why does his umbilical chord emerge with him, [so] he hangs from the belly, and his mother [has to] cut it? And this that you said 'Why doesn't he emerge circumcised?', [the reason is] because the Holy One Blessed is He gave the Israel the commandments only in order to refine them [Israel] through them [the commandments]. And that's why David said (Psalms 18:31) (all) 'the word of the LORD is refined.'"
Circumcision makes it clear as can be that you are here and not there, that you are out and not in – also that you’re mine and not theirs...Quite convincingly, circumcision gives the lie to the womb-dream of life in the beautiful state of innocent prehistory, the appealing idyll of living ‘naturally,’ unencumbered by man-made ritual. To be born is to lose all that. The heavy hand of human values falls upon you right at the start, marking your genitals as its own.
I think the interesting question is not why I circumcise my son but what happens when I circumcise him. A week ago I found out what was going on. I participated in a religious ceremony in the time-honored sense of the word.
This is a meaning that is gradually being lost, in a time when choosing to be religious is based on “what’s in it for me”: observing shabbat is social, sitting shiva is psychological, modesty expresses innocence lost. In modern times, religious laws have become passe and have gotten away from the notion that they are a Divine command. So here's a slice of a commandment that defies logic. When I circumcised my son, I felt for the first time in ages that I am observing mitzvot, commandments, not only because they are worthwhile, because they are healthy. I observe mitzvot because that is what God commanded.
(ה) רַבִּי יִשְׁמָעֵאל וְרַבִּי עֲקִיבָא, רַבִּי יִשְׁמָעֵאל אוֹמֵר אַבְרָהָם כֹּהֵן גָּדוֹל הָיָה, שֶׁנֶּאֱמַר (תהלים קי, ד): נִשְׁבַּע ה' וְלֹא יִנָּחֵם אַתָּה כֹהֵן לְעוֹלָם וגו', וְנֶאֱמַר לְהַלָּן (בראשית יז, יא): וּנְמַלְתֶּם אֵת בְּשַׂר עָרְלַתְכֶם, מֵהֵיכָן יִמּוֹל, אִם יִמּוֹל מִן הָאֹזֶן אֵינוֹ כָּשֵׁר לְהַקְרִיב, מִן הַפֶּה אֵינוֹ כָּשֵׁר לְהַקְרִיב, מִן הַלֵּב אֵינוֹ כָּשֵׁר לְהַקְרִיב, מֵהֵיכָן יִמּוֹל וְיִהְיֶה כָּשֵׁר לְהַקְרִיב, הֱוֵי אוֹמֵר זוֹ עָרְלַת הַגּוּף. רַבִּי עֲקִיבָא אוֹמֵר אַרְבַּע עֲרָלוֹת הֵן, נֶאֶמְרָה עָרְלָה בָּאֹזֶן (ירמיה ו, י): הִנֵּה עֲרֵלָה אָזְנָם, וְנֶאֶמְרָה עָרְלָה בַּפֶּה (שמות ו, ל): הֵן אֲנִי עֲרַל שְׂפָתַיִם, וְנֶאֱמַר עָרְלָה בַּלֵּב (ירמיה ט, כה): וְכָל בֵּית יִשְׂרָאֵל עַרְלֵי לֵב, וְנֶאֱמַר עָרְלָה בַּגּוּף (בראשית יז, יד): וְעָרֵל זָכָר, וְנֶאֱמַר לוֹ: הִתְהַלֵּךְ לְפָנַי וֶהְיֵה תָמִים, אִם יִמּוֹל מִן הָאֹזֶן אֵינוֹ תָּמִים, מִן הַפֶּה אֵינוֹ תָּמִים, מִן הַלֵּב אֵינוֹ תָּמִים, וּמֵהֵיכָן יִמּוֹל וְיִהְיֶה תָמִים, הֱוֵי אוֹמֵר זוֹ עָרְלַת הַגּוּף. מִקְרָא אָמַר (בראשית יז, יב): וּבֶן שְׁמֹנַת יָמִים יִמּוֹל לָכֶם כָּל זָכָר לְדֹרֹתֵיכֶם, אִם יִמּוֹל מִן הָאֹזֶן אֵינוֹ שׁוֹמֵעַ, מִן הַפֶּה אֵינוֹ מְדַבֵּר, מִן הַלֵּב אֵינוֹ חוֹשֵׁב, מֵהֵיכָן יִמּוֹל וְיִהְיֶה יָכוֹל לַחֲשֹׁב, זוֹ עָרְלַת הַגּוּף. אָמַר רַבִּי תַּנְחוּמָא מִסְתַּבְּרָא הָדָא מִקְרָא וְעָרֵל זָכָר, וְכִי יֵשׁ עָרֵל נְקֵבָה, אֶלָּא מִמָּקוֹם שֶׁהוּא נִכָּר אִם זָכָר אִם נְקֵבָה מִשָּׁם מוֹהֲלִים אוֹתוֹ.
(5) (5) R' Yishmael and R' Akiva: R' Yishmael says, Avraham was a High Priest, as it says (Ps. 110:4), "The LORD has sworn and will not relent, 'You are a priest forever, etc.'" and it says elsewhere (Gen. 17:11), "You shall circumcise the flesh of your foreskin." From where should he be circumcised? If he is circumcised from the ear, he is not fit to offer sacrifices. From the mouth, he is not fit to offer sacrifices. From the heart, he is not fit to offer sacrifices. Where should he be circumcised so that he will be fit to offer sacrifices? You must say it is the foreskin of the body. R' Akiva says, there are four foreskins. Foreskin is said with regard to the ear (Jer. 6:10): "Their ears are blocked." Foreskin is said with regard to the mouth (Exod. 6:12): "me, a man of impeded lips." Foreskin is said with regard to the heart (Jer. 9:25): "but all the House of Israel are uncircumcised of heart." Foreskin is said with regard to the body (Gen. 17:14): "male who is uncircumcised [one who is uncircumcised in his maleness]." It was said to him, (Gen. 17:1): "Walk in My ways and be blameless/whole." If he is circumcised from the ear, he is not whole; from the mouth, he is not whole; from the heart, he is not whole. From where should he be circumcised so that he will be whole? You must say it is the foreskin of the body. Scripture says (Gen. 17:11-12), "[You shall circumcise the flesh of your foreskin, and that shall be the sign of the covenant between Me and you.] And throughout the generations, every male among you shall be circumcised at the age of eight days." If he is circumcised from the ear, he cannot hear; from the mouth, he cannot speak; from the heart, he cannot think. From where should he be circumcised so that he can think? This is the foreskin of the body. R' Tanhuma said, tis Scripture makes sense (Gen. 17:14): "male who is uncircumcised [one who is uncircumcised in his maleness]." And does there exist one who is uncircumcised in femaleness? Rather, from the place where it is recognized whether male or female -- from there we circumcise him.
Additional (Phenomenal) Reading
The Best Place on Earth by Ayelet Tsabari, Brit Milah, pg. 47-69