Avraham was extremely careful that Yitzchak not marry a Canaanite and as we know, he married Rivkah bas Besuel ben Nachor. Yitzchak was very careful that Ya'akov not marry a Canaanite and as we know he married Leah and Rachel bnos Lavan ben Besuel ben Nachor. The pasuk in VaYeishev specifically says that Yehudah married the daughter of Shua the Canaanite. VaYigash says that Shimon's youngest son Shaul was a son of a Canaanitess.

Sefer HaYashar to Parshas VaYeishev (Chapter 45) says as follows:

"Then Re'uven ben Ya'akov went towards Timnas and took Elioram bas Evi the Canaanite for a wife for himself and he came to her. She conceived and Elioram wife of Re'uven bore him Chanoch and Pallu and Chetzron and Karmi four sons. And Shimon his brother had taken Dinah his sister for a wife and she bore him Yemuel and Yamin and Ohad and Tzochar five sons. And after that, Shimon had come to Bonah the Canaanite that is Bonah who Shimon had captured from the city of Shechem. Bonah was before Dinah and she attended to her and Shimon came to her and she bore him Shaul. And Yehudah had gone at that time to Adulam and he turned to an Adullamite man and his name was Chirah. Then Yehudah saw there a daughter of a Canaanite man and her name was Eilis bas Shua and he took her and he came to her. Then Eilis bore to Yehudah Er and Onan and Shelah three sons."

The rest of the brothers do not marry Cana'anites, Levi and Yissachar marry two granddaughters of Yoktan ben Ever. Dan marries a Moabite. Gad and Naphtali marry two great-granddaughters of Nachor. Asher marries a Yishmaelite and then a granddaughter of Yoktan. Zevulun marries a Midianite (discussed here The wife of Zevulun (Sefer HaYashar)). Binyamin marries an Aram-Zovah-ite and a daughter of Zimran ben Avraham. Yehudah then Tamar bas Eilam ben Shem and Yoseph marries Osenas.

Why was Ya'akov not so careful that his sons not marry Canaanites?

In addition, I heard that Osenas was actually the daughter that Dinah had with Shechem, which would make Osenas a Canaanite as well.

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    If Osnas was the daughter of Dinah who was a Jewish Mother, she's automatically Jewish. – Al Berko Dec 1 '18 at 19:27
  • @AlBerko it’s possible that before matan torah identity worked according to patrilineal descent. Nevertheless, you can hardly consider Dinahs daughter a true Caananite. She would possess some Jewish character. – LN6595 Dec 2 '18 at 2:34
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    I don't want to get downvoted, But I feel it's my obligation to point out something I found out while learning Midrashim for a While. Almost all Medrashim are written IE Edited by the Holy and Great Tannaim. But Sefer Hayashar is different in several ways and considered much less reliable. #1 The Vast majority of Sefer Hayashar tells stories in detail that I nor my Rabbim ever heard. #2 Sefer Hayashar brings down many names (Of Wives, family members, friends) sometimes contradicted by Meforshim #3 Many Printings say that the Person who claims he found the Book might've written it. – Sochacz Jan 4 at 17:10

According to Pesahim 50a, the very premise of the question; that Jacob's sons married Canaanite women is wrong. Indeed, the very notion is so inconceivable that that the Talmud interprets Genesis (38:2) as not implying that Judah married a Canaanite wife:

דכתיב 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

For it is written 'And there Judah saw the daughter of a Canaanite man'. What is meant by Canaanite? If you say an actual Canaanite, is it possible that Abraham warned Isaac, and Isaac warned Jacob [not to marry Canaanites] and Judah went and marries [one]? Rather Said R. Simon ben Lakish, [it means that] she was the daughter of a merchant.

According to R. Hayyim Paltiel (Genesis 37:35) even according to the opinion that the tribes married Canaanites, it is possible that they weren't ethnic Canaanites, but only resident there:

ר' יהודא אמר כנעניות היו. וצ"ע דסוף פרק אילו עוברין אמרינן בת איש כנעני אילימא בת כנעני ממש, אי אפשר, בא אברהם והזהיר בא יעקב והזהיר ויהודה נשא כנענית, ואילו הכא אמרינן השבטים נשאו כנעניות... ושמא י"ל דלא היו אלא מארץ כנען

Based on the above understanding the the brothers didnt marry Canaanites, Simon seems to be the exception that proves the rule. As Radak writes in Genesis (38:2):

בת איש כנעני ...וכנעני כתרגומו סוחר היה משאר האומות והתגורר שם, כי בני יעקב היו נזהרים מלהתחתן עם בנות כנען כמו האבות, כי שמעון שלקח אשה מבנות כנען זכרו לגנאי והפרידו מאחיו ואמר ושאול בן הכנענית:

The daughter of a Canaanite...And 'Canaanite' is identical in meaning to its Targumic explanation; that he was a merchant from a different nation [other than Canaan]. For Simon who took a wife from the daughters of Canaan, was mentioned negatively, and [listed] separately from his brothers, and it is said 'and Saul the son of the Canaanite'.

See also Ramban to Genesis (38:2).

  • This helps with all except Osenas because being the daughter of Shechem ben Chamor, king of Shechem, he surely must have been an actual Canaanite? – Joshua Pearl Mar 5 '17 at 20:55
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    The Talmud apparently isnt going with that idea. Furthermore, I have no idea why Rabbenu Hayyim Paltiel's answer is any less relevant to Shekhem ben Hamor. Who says he was an ethnic Canaanite. Lastly, we don't know what the Avot would've thought about partial Canaanites. – mevaqesh Mar 5 '17 at 21:07
  • @mevaqesh This suffers from circular reference. They weren't Canaanite because they could not be Canaanite. Case closed. Why R'Yehuda does say Canaanites Mamash? – Al Berko Dec 9 '17 at 23:54
  • @AlBerko I have no idea what you are talking about. I made no circular reference (and suspect you don't know what a circular reference is. Perhaps you are confusing this with circular reasoning, which of course, this isn't either.) They weren't Canaanites because that is what the commentators say; not because they weren't Canaanites. I didn't quote R. Yehuda, in this post. If you are asking about the opinion, כנעני ממש, Rabbenu Hayyim Paltiel addressed that. || The post is quite clear, and written in fine English, I don't think anything I write in comments could be any clearer. [cont.] – mevaqesh Dec 10 '17 at 0:24
  • @AlBerko There is no point of leaving a comment that is indecipherable anyway. You may as well neaten up the comment section be deleting your comment, posting a clearer version of it if you are absolutely positive it has some merit. – mevaqesh Dec 10 '17 at 3:44

R' Moshe Luriah addresses this question following the to Ariz"L tradition (a little Kabbalic though).

  1. There are two sorts of "bad" - a "not so bad" bad and "really bad" bad. The former, if dealt properly, can be "converted" and useful, the other cannot be "converted" and used.

  2. Examples of the first type are: אשת יפת תואר that can be slept with and converted and חזיר that's allowed to be eaten, both in certain conditions by certain people, but not others.

  3. Examples of the second type are the seven nations in the Holy Land that can not be converted or even enslaved and have to be completely exterminated (after Matan Torah). Or Amolek.

  4. The prohibition of marrying Canaanites was valid for Itzhak and Yaakov because of their personal qualities, but the Tribes were already different. The had the qualities to override the טומא of the Canaanites and put them into Keddushah.

  5. Not only that was "allowed" for them but it was a bigger Mitzvah as this would weaken the Canaanites. That was true for Yossef taking Osnat of Putifera and Moses taking Tziporah of Medyan etc.

I'm aware of the fact that most interpreters feel uncomfortable with the Pshat of the Torah and try to skew it but they shouldn't.

  • I'm up voting you because of your personal comment at the end. – Aaron Dec 3 '18 at 1:08

Source for אסנת being Dina’s daughter is מסכת סופרים 21:9

בת שש שנים היתה דינה כשהולידה את אסנת משכם מנין שש שנים של שכר הצאן שעבד יעקב אבינו ללבן והוסיף עשרים שנה שמת מכאן ואילך יוסיף המבין דעת וירד מיכאל והוליכה לבית פוטיפר

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