Orthodox rabbi Jack Abramowitz came to realize that gender issues in halacha are far more intricate than many would assume.
Recently, I received an inquiry from someone who was researching transgender issues in halacha. The first thing I told them, before suggesting some sources, was that this issue is far above my pay grade. I am not qualified to comment on the permissibility of any course of action and I can make no recommendations. All I can do is direct them to information. With that understanding in mind, there’s an observation I have since made that is important to share. Some might find this controversial but I don’t think it is. It’s certainly not intended to be. I’m not saying anything of my own invention, I’m just connecting the dots.
Our forefather Yaakov had four wives: Rachel and Leah were sisters; Bilha and Zilpah were their servants (“handmaidens”). They knew that among them, they were destined to bear twelve Tribes. At one point, Leah had six sons, Bilha had two, Zilpah had two, and Rachel had none. Rachel and Leah both became pregnant. Leah realized, “If I have a son, that will be eleven and my sister Rachel will only be able to bear one Tribe – less than our servants!” Out of concern for Rachel’s honor, Leah prayed and God made a miracle. According to the version of the Midrash cited by Rashi, the baby in Leah’s womb – originally intended to be a boy – was turned into a girl (Genesis 30:21 – actually citing a Gemara in Brachos). Another Midrashic understanding is that God switched the embryos in Rachel and Leah’s wombs (Targum Yonasan).
This Midrash has occasionally been used to explain anomalous behavior in Dina (Leah’s daughter) and Yosef (Rachel’s son). At a time when women were typically homebodies sticking to their tents, Dina was outgoing and inquisitive (Bereishis Rabbah), arguably the result of her male origins. Similarly, Yosef was more concerned with his appearance, such as his hair and his clothes, than any of his brothers (ibid). This can potentially be attributed to his female roots.
Michal, the daughter of King Saul and the wife of King David, used to put on tefillin. (Whether this was allowed differs between Talmud Bavli and Yerushalmi – Eiruvin 96a and Brachos 2:3.) Kabbalistically, Michal possessed a soul that was male in a previous incarnation (Kaf HaChaim OC 38:9). This does not appear to be the result of a miracle as with Dina and Yosef. Here are people who, for whatever reason, went against their gender norms. It’s important to note that this characteristic is not attributed to Lavan, Pharaoh or Haman. The people described as having tendencies that were not gender normative were tzaddikim (righteous people). They are heroes in the story.
It shouldn’t come as a surprise that Judaism is traditionally rigid when it comes to gender roles. Deuteronomy 22:5 contains two separate prohibitions against cross-dressing, one for men not to wear women’s clothes and vice versa. There are similarly a number of practices that are limited to one gender or the other.