The Torah takes a break in the middle of Joseph’s tale to give us the story of Judah (or maybe it was always his story). It begins with Judah “descending” from his brothers - we will come back to that. He then marries a Canaanite women. This is surprising considering that until now all of the forefathers have tried to get their children to not marry Canaanites.
בראשית פרשת וישב פרק לח
Genesis Chapter 38
(1) Then it was at that time that Judah descended from his brothers and turned to an Adullamite man whose name was Chirah.
(א) וַיְהִי בָּעֵת הַהִוא וַיֵּרֶד יְהוּדָה מֵאֵת אֶחָיו וַיֵּט עַד־אִישׁ עֲדֻלָּמִי וּשְׁמוֹ חִירָה:
(2) Then Judah saw there the daughter of a Canaanite man whose name was Shua; then he took her [as a wife] and went to her.
(ב) וַיַּרְא־שָׁם יְהוּדָה בַּת־אִישׁ כְּנַעֲנִי וּשְׁמוֹ שׁוּעַ וַיִּקָּחֶהָ וַיָּבֹא אֵלֶיהָ:
בראשית פרשת חיי שרה פרק כד
Genesis Chapter 24
(2) Then Abraham said to his servant, the elder of his house in charge of all that was his, “Place your hand under my thigh.
(ב) וַיֹּאמֶר אַבְרָהָם אֶל־עַבְדּוֹ זְקַן בֵּיתוֹ הַמֹּשֵׁל בְּכָל־אֲשֶׁר־לוֹ שִׂים־נָא יָדְךָ תַּחַת יְרֵכִי:
(3) “And swear to me by Hashem, God of the Heavens and God of the earth, that you will not take a woman for my son from the sons of the Canaanites amongst who I dwell.”
(ג) וְאַשְׁבִּיעֲךָ בַּיקֹוָק אֱלֹהֵי הַשָּׁמַיִם וֵאלֹהֵי הָאָרֶץ אֲשֶׁר לֹא־תִקַּח אִשָּׁה לִבְנִי מִבְּנוֹת הַכְּנַעֲנִי אֲשֶׁר אָנֹכִי יוֹשֵׁב בְּקִרְבּוֹ:
בראשית פרשת תולדות - ויצא פרק כז - כח
Genesis Chapters 27-28
(מו) וַתֹּאמֶר רִבְקָה אֶל־יִצְחָק קַצְתִּי בְחַיַּי מִפְּנֵי בְּנוֹת חֵת אִם־לֹקֵחַ יַעֲקֹב אִשָּׁה מִבְּנוֹת־חֵת כָּאֵלֶּה מִבְּנוֹת הָאָרֶץ לָמָּה לִּי חַיִּים:
(46) Then Rebecca said to Isaac, “My life is cut short by the daughters of Chet, lest Jacob take a woman from the daughters of Chet like these of the daughters of the land; why should I live.”
(א) וַיִּקְרָא יִצְחָק אֶל־יַעֲקֹב וַיְבָרֶךְ אֹתוֹ וַיְצַוֵּהוּ וַיֹּאמֶר לוֹ לֹא־תִקַּח אִשָּׁה מִבְּנוֹת כְּנָעַן:
(1) Then Isaac called to Jacob, then blessed him and commanded him, saying to him, “Do not take a woman from the daughters of Canaan.”
We see earlier in Genesis that Chet was the younger son of Canaan.
בראשית פרשת נח פרק י
Genesis Chapter 10
(טו) וּכְנַעַן יָלַד אֶת־צִידֹן בְּכֹרוֹ וְאֶת־חֵת:
(15) And Canaan sired Tzidon his first-born and Chet.
However, we have two places in Tanakh where the word K’naan [כנען] means “merchant” or “trader,” and not an actual Canaanite.
ישעיהו פרק כג
Isaiah Chapter 23
(8) Who counsels this against Tyre the crowned whose merchants are princes, traders [kinane-ha] are the respected of the land.
(ח) מִי יָעַץ זֹאת עַל־צֹר הַמַּעֲטִירָה אֲשֶׁר סֹחֲרֶיהָ שָׂרִים כִּנְעָנֶיהָ נִכְבַּדֵּי־אָרֶץ:
הושע פרק יב
Hosea Chapter 12
(ח) כְּנַעַן בְּיָדוֹ מֹאזְנֵי מִרְמָה לַעֲשֹׁק אָהֵב:
(8) A merchant [k’naan] has deceitful scales in his hand; he loves to oppress.
The translation of Yonatan into Aramaic translates Canaanite as “merchant” in the Judah story (among his other interesting changes).
תרגום יונתן בראשית פרשת וישב פרק לח
Translation of Yonatan, Genesis Chapter 38
(2) Then Judah saw there the daughter of a merchant man and his name was Shua, converted her and went to her.
(ב) וחמא תמן יהודה ברת גבר תגר ושמיה שוע וגיירה ועל לותה:
The Talmud takes the approach that Judah must have married a merchant, not an actual Canaanite.
תלמוד בבלי מסכת פסחים דף נ עמוד א
Babylonian Talmud, Tractate P’sachim, 50a
“Then Judah saw there the daughter of a Canaanite man.” What is a “Canaanite”? If one says it is an actual Canaanite, is it possible that Abraham came and prohibited Isaac, came Isaac and prohibited Jacob, and Judah went and married one? Rather, said Rebbi Shimon son of Lakish, “It is the daughter of a merchant man, as it says, “A merchant [C’naan] has deceitful scales in his hand,” (Hosea 12:8). And if you want to say [a different source], it is from here: “Whose merchants are princes, traders [kinane-ha] are the respected of the land,” (Isaiah 23:8).
וירא שם יהודה בת איש כנעני. מאי כנעני? אילימא כנעני ממש - אפשר בא אברהם והזהיר את יצחק, בא יצחק והזהיר את יעקב, ויהודה אזיל ונסיב? אלא אמר רבי שמעון בן לקיש: בת גברא תגרא, דכתיב "כנען בידו מאזני מרמה," (הושע יב:ח). ואיבעית אימא מהכא "אשר סחריה שרים כנעניה נכבדי ארץ," (ישעיהו כג:ח).
However, whether Judah (and potentially the other brothers) married a Canaanite woman is a debate in Genesis Rabbah, based on the following verse. The verse describes Jacob’s sons and daughters attempting to comfort him after the supposed death of Joseph. It is confused about who are his daughters.
בראשית פרשת וישב פרק לז
Genesis Chapter 37
(35) Then all of his sons and all of his daughters got up to comfort him, but he refused to be comforted and said, “I will go down to my son in mourning to the grave;” then his father wept for him.
(לה) וַיָּקֻמוּ כָל־בָּנָיו וְכָל־בְּנֹתָיו לְנַחֲמוֹ וַיְמָאֵן לְהִתְנַחֵם וַיֹּאמֶר כִּי־אֵרֵד אֶל־בְּנִי אָבֵל שְׁאֹלָה וַיֵּבְךְּ אֹתוֹ אָבִיו:
Rebbi Yehuda, in the midrash, takes the opinion that each tribe (i.e. son of Jacob) married a sister. In other versions of this midrash it says each married a twin sister. Rebbi Nechemiyah argues that the “daughters” in the verse were Canaanite wives of the sons of Jacob and that daughters-in-law are also called daughters. While Rebbi Yehuda solves the issue of the sons of Jacob marrying Canaanites, it does so with an even more chilling set of relationships.
בראשית רבה (תיאודור-אלבק) פרשת וישב פרשה פד:יט
Genesis Rabbah (Theodore Albek Edition), Parasha 84:19
Rebbi Yehuda says, “Each of the tribes married their sister, thus it says, ‘Then all of his sons and all of his daughters got up.’”
ר' יהודה א' לאחיותיהם נשאו השבטים הה"ד ויקומו כל בניו וכל בנתיו וגו'
Rebbi Nechemiyah says, “They were Canaanites… rather, a person is not prevented from calling his son-in-law, ‘Son,’ and daughter-in-law, ‘Daughter.’”
ר' נחמיה א' כנעניות היו… אלא אין אדם נמנע לקרוא לחתנו בנו ולכלתו בתו.
Rebbi Eliyahu Mizrachi, based on two conflicting Rashis, tries to reconcile the opinion of Rebbi Nechemiyah in Genesis Rabbah with the Talmud. He says that Judah did marry a merchant because as the king of the sons (as Jacob later addresses him and his line later upholds) he has the option to marry outside of the local Canaanites. However, the other brothers have no choice. They have no ability to take wives from Haran as did Isaac and Jacob. According to this, maybe it was only Judah, the son who most continues the line of tradition, who may not marry outside of the Abrahamic family.
רבי אליהו מזרחי בראשית פרשת ויחי פרק נ
Rebbi Eliyahu Mizrachi on Genesis Chapter 50
Eliyahu of Constantinople, 15th and 16th Centuries
There is to say that Judah is different, for he was a king and he had the power to marry a woman from any nation he desired. But his brothers, for them it was only possible to marry daughters of Canaanites among whom they dwelled, they could not.
יש לומר, שאני יהודה שהיה מלך והיה ספק בידו לישא אשה מאי זו אומה שהיה רוצה, אבל אחיו דלא הוה אפשר להו לישא אלא מבנות כנען שהיו דרים עמם, לא.
The Maharsha thinks the Talmud agrees with Rebbi Yehuda that the sons of Jacob married their sisters. He goes as far as to say that the prohibition of marrying a Canaanite predates the prohibition on marrying a sister. He might even be implying - though this is only speculation - that the former is worse than the latter.
מהרש"א חידושי אגדות מסכת פסחים דף נ עמוד א
Maharsha, Novella on Narrative, Tractate P’sachim 50a
Shmuel Eidels, 16th and 17th Centuries Poland
And it seems that our Talmud reasons like Rebbi Yehuda who says in Genesis Rabbah that they did not marry Canaanites; rather that born with each one of them was a twin sister and they married them.
ונראה דתלמודינו מצי סבר כרבי יהודה דאמר בב"ר דלא נשאו כנעניות אלא דאחיות תאומות נולדו עם כ"א מהם ונשאום
And even though this is an issue that the Torah will later forbid, the children of Jacob were not prohibited in it like they were prohibited in marrying the daughters of Canaan in that we see explicitly in the text that the forefathers were prohibited in it; investigate and you find this simply.
ואע"ג שהוא דבר שעתידה התורה לאסור לא הוזהרו בו בני יעקב כמו שהוזהרו מלישא בנות כנען שמצינו מפורש בקרא שהוזהרו בו האבות ודו"ק:
The Gur Aryeh takes a different approach. He thinks that the prohibition against marrying a Canaanite only applied when the Abrahamic offspring had not yet cohered into a nation: when there were twelve brothers. Once that happened, a Canaanite marrying in becomes absorbed into Israel.
גור אריה בראשית פרשת וישב פרק לח
Gur Aryeh on Genesis Chapter 24
Yehuda Loeb, 16th Century Poland
And if you say that Rebbi Nechemiyah who thinks that they were Canaanites is challenged by, “Is it possible that Abraham came and prohibited, etc.” One can respond that this was only when the twelve tribes of Israel were not yet born, that is the sons of Israel. If they [before the tribes] had married Canaanites, they would not have been absorbed within the general structure of Israel. But once there were twelve tribes - and they were considered as a people - as is written about about Shechem son of Chamor, “Then we will be one nation,” (Genesis 34:16). But before this they were two nations. If so, they became a people once the tribes were born.
ואם תאמר ור' נחמיה דסבירא ליה דכנעניות היו תקשה ליה "אפשר בא אברהם והזהיר וכו'', ויש לומר דוקא כאשר עדיין לא נולדו י"ב שבטי ישראל שהם בני ישראל - אם היו נושאים כנעניות לא היו בטלים בתוך כלל ישראל, אבל כאשר היו כל י"ב שבטים - ונחשבו לאומה - כדכתיב למעלה אצל שכם בן חמור "והיינו לעם אחד," (בראשית לד:טז) , וקודם לכן - היו שני אומות, אם כן שם אומה עליהם מיד שנולדו השבטים,
And once they were considered one nation, there is no prohibition in this. For anyone who attaches to a nation is like that nation and [has their previous identity] completely canceled to them and are completely considered Israelites.
וכאשר נחשבו לאומה אין איסור בזה, לפי שכל המתחבר לאומה הרי הוא כאומה ובטילה אצלם לגמרי, ונחשב בכלל ישראל.
The Chatam Sofer does not think that Judah’s marrying a Canaanite who was really a merchant, not an actual Canaanite, is not so helpful. After all, a Canaanite is not just any merchant but one who sells to the poor. Based on the verses we saw, such a merchant is one who, in selling to the poor, is able to cheat them. He carries deceitful scales and loves oppression. The point of teaching us Judah married a Canaanite - meaning merchant - is to teach us these types of merchants are not people one should associate with. For background, he is actually commenting on the verse from the end of Proverbs “וחגור נתנה לכנעני” (She sells belts to the Canaanite/merchant).
חתם סופר מסכת פסחים דף נ עמוד א
Chatam Sofer, Tractate P’sachim 50b
Moshe Sofer, 18th and 19th Century Austria-Hungary
It seems, in my humble opinion, that for sure the text does not budge from its meaning. For sure a Canaanite is a merchant, but he is a merchant who sells little by little to the poor for pennies and the like...
הנלע"ד דודאי קרא אינו זז ממשמעותיה לעולם דכנען הוא תגר אך הוא תגר המוכר על יד על יד לעניים בפרוטה וכדומה...
Therefore it is derived from Judah. For sure it follows like this [that it is a merchant to the poor], for if it were not so, what do we learn that he married the daughter of a Canaanite once we learn this is not an actual Canaanite? Rather, to teach us that he descended from his brothers, as Rashi explains, that he descended from his greatness and married a “Canaanite” that is a minor merchant which was not according to his honor and high status. Or it says that he married the daughter of a Canaanite whose way it is to benefit from theft and to have in his hands deceitful scales.
לכן מייתי מיהודה דודאי משמע דהכי הוא דאל"כ מאי קמ"ל שנשא בת איש כנעני כיון דלאו כנענית ממש הוה א"כ מאי קמ"ל בזה אע"כ להשמיענו שירד מאת אחיו כפרש"י שירד מגדולתו ונתחתן עם כנעני שהוא תגר קטן שאינו לפי כבודו וגדלו או יאמר דנשא בת כנעני שדרכו להנות מן הגזל ולהיות בידו מאזני מרמה
If I may, humbly, attempt to tie this together, perhaps the entire issue with Canaanites is that they are unscrupulous merchants, which may be hinted at in the story of Abraham buying a plot for Sarah’s grave.