Toldois 2025: Reincarnation & Transgenderism

by devadmin | November 20, 2025 9:38 pm

Raboyseyee and Ladies,

We begin with mazel tov wishes to our friends Deena & Marc Intrator upon the upcoming wedding this coming Sunday on their amazing son Samuel Elliot (AKA: Sammy) to Abigal Rose Minkove, she the beautiful daughter of Elana & Shami Minkove. We look forward to participating in this most joyous event and wish Abigail and Sammy many years of blissful marriage ahead. Mazel tov to both immediate and extended families.


Yashar koach to Esther and Chaim Kopel (he better known as Howard, the Deputy Presiding Officer of the Nassau County Legislature and Legislator of the 7th District of Nassau County) for hosting the heylige Ois and eishes chayil for lunch this past Shabbis, where the meal and ambiance were perfect. Esther, who hails from a well-known dynastic rebbishe family is no slouch either; that for another time.

Reincarnation & Transgenderism

From time to time, I quote and share what the kabbalists say about a certain topic, but what is kabolo? Did the RBSO share any with us? Can anything about kabolo be found in the Heylige Toirah? Anywhere? In the Mishnah or in the heylige Gemora? How about in the medrish where all fantasies come to life? Drumroll…..and the answer is no, no, no, and no! Oib azoy (that being the case), how did it get here? Why do certain people study it, and swear by it? Why do many quote it when groping for answers to difficult questions? Is it real?

Shoin, let’s start with its main talking point and that is gilgul. What is gilgul? Gilgul is the reincarnation of the soul (only). In kabolo, the neshomo (soul), or part of it, returns in another body to complete its unfinished spiritual work, whatever that means. That being stated, the Ois repeats this: There is zero explicit mention of reincarnation in the Heylige Toirah: No posik says the souls come back, no narrative describes it, and not a single mitzvah or commandment references it. If that’s the case -seemingly it is- who came up with it, and why did people buy in? Is it mamish but a made-up concept? Finally, why is the Ois leading with it?


And the answers raboyseyee and ladies include these: First of all, there is a theory some kabbalists put forth suggesting that Rivka, central character of this week’s parsha, may have been a gilgul; she was, or may have been, someone else in a prior life but came back. Shoin.

Just so you know, there is some discussion about reincarnation dating back to the 11th century but it seems to have come to life -pun intended- back in the 16th century when the Arizal reduced his thoughts to writing. The bottom line: kabolo for real is only a few hundred years old and only appeared years after the heylige Toirah was given over 3000 years back.  In other words: it’s still rather newish. Another bottom line: A handful of rabbis -mostly themselves kabbalists or at least believers- decided that certain passages in the Heyilge Toirah hint to the concept of reincarnation and rectification. And shoin, kabolo was born, marketed, and since, accepted by many luminaries. Of course, not all, as some -listed by name later- are adamant that this is all nothing but narishkeyt (nonsense) and BS. Those who lead the movement said with a degree of certitude, that there are two or three aggadic sugyos in the heylige Gemora that some later kabbalists reinterpret as hints to this line of thinking. Pshat being that the words lend themselves to kabbalisitc interpretation. Let’s check them out.

That said, these Gemora citations never mention reincarnation. Not once. But don’t these concepts come to life in the medrish where everyone is given license to imagine or interpret? Is gilgul in the medrish? So you know and chap, classical midrashim (Bereishis Rabbah, Tanchuma, Mechilta, Sifrei, etc.) do not discuss gilgul.  For full disclosure: Later midrashic-style mystical books do, but those are NOT part of Chazal.  Who says what and why? Gilgul entered Jewish thought much later through the Bahir (1100s), the Zohar (1280s–1300s Spain), and  the Arizal (1500s Tzfas). You may not have heard about the Bahir of the 11th century but kimat all readers did hear about the heylige Zoihar (13th century) who put out a major mystical elaboration, and in the 16th century, the Arizal systematized the entire doctrine in Sha’ar HaGilgulim. The bottom line: you may not know them but it’s entirely possible that they knew you. Hec, you might have been one of their contemporaries in your earlier iteration of yourself, ver veyst!?

And with that introduction, let us dig into Parshas Toldois which features the birth of Yaakov and Eisav, and a most famous story which has Yaakov -with the help of his very creative mother, Rivka- concoct a plan to outwit his twin brother Eisav. And in our sixteenth time around Parshas Toldois, let’s get mystical.  As mentioned in the opening paragraph, from time to time, the heylige Ois will take a look at the Zoihar, Arizal, Targum Yoinoson Ben Uzeil, and others, because they, besides being great mystics, also had mamish very vivid and wild imaginations. This week, they will try to convince us that it’s efsher possible that Rivka Emanu, she the wife of Yitzchok Ovenu -our second forefather, and sister of that conniver Lovon who will -in next week’s parsha- become the father-in-law of Yaakov, was mamish a gilgul (reincarnation) of Chava. She was what? One more time: they say that Rivka – central character of this week’s parsha- was mamish a reincarnation of Chava. Wait, there’s more: Says the heylige Zoihar -as quoted by the Beni Yisoschor- that Yaakov -whom we will meet very early in the parsha- came down to this world to do ‘tikkun’ (rectification) for sins committed by Odom (Adam) and that Eisav, his twin older brother, was somehow connected to the nochosh (snake). Aren’t we all, if you chap? In other words: the entire starting lineup featured in our parsha, is comprised of past celebrities who have been reincarnated for the storyline in our parsha. Wow! Is your head spinning yet?

Shoin, let’s begin by going over what the Arizal – he most famous for shrinkage in the coldest mikveh in the world- had to say about this Rivka/Chava gilgul. WARNING: Many times, views coming from these giants among men, will be vild (wild) mamish and will typically also contain some sexual content. Don’t blame the Ois; He’s mamish but either quoting or paraphrasing what these great men had to say. And how great was Reb Yoinoson ben Uzeil? Heck, his interpretations -as he imagined them- made their way in the finest version of the Chumish -the big one- the Mikro’ois Gidoilois- the version that yeshiva boys get as bar mitzvah presents never to be seen again until they move out, and the very version that our finest high schools want our boys to purchase so that it appears as if they are leaning something. They don’t! They can barely read.

Anyway, said the Arizal azoy: Rivka was indeed a gilgul (reincarnation) of Chava, the first woman. Shoin! She was? Why taka are people reincarnated? That avada depends on whom you ask ober, hakol moidim (all agree) that one of the main reasons for reincarnation is so that the new ‘he/she’ can rectify the sins that were committed in an earlier lifetime by the old ‘he/she.’ Taka, when a he acts like, or becomes a she, and farkert, there are usually a few sins that require rectification. In plain English: the erectification, if you chap, was in the wrong place. Reincarnation and rectification are closely related. So happens that in kabolo, which dates back a few centuries -way before transgender was a thing- and even without costly and painful surgical procedures, a he can come back as a she, and vice versa. Indeed, a woman’s soul can reincarnate into a man. Mamish! Says the Arizal: Souls are not “male” or “female” in essence. They have a root (shoresh), and their mission determines whether they come as Male, female, or sometimes both across multiple lives. Don’t question the messenger but this information is explicit all over the Sha’ar HaGilgulim, especially in Chapter 9, 20–22, 34, and 38. As an aside, there are cases where the soul can come back as an dog or other such animal or creature; that for another day.

Why does a soul switch genders? Because the tikkun (repair) needed changes. Sometimes: A female soul returns as male to complete a mitzvah obligation and at other times, a male soul returns as female to correct emotional, relational, or spiritual aspects. Confused? You are not alone; so are the hyntige (todays) transgenders. And says the Arizal that some biblical figures switched genders across lifetimes — he doesn’t mean physically in this life, but in reincarnations across generations. Well, blow me down.

And before I start hearing from that community, avada there are major differences between gilgul and transgenders, but know these factoids: the heylige Ois writes with humor and sarcasm. That said, both involve a change of sex or gender. In Kabolo, a soul can be reincarnated (gilgul neshomo) into a new body. Sometimes, a soul that was in a male body may return in a female body, or vice versa. The change of sex is not about identity or social roles, but purely the soul’s journey and spiritual mission. On the other hand, transgender people experience a mismatch between their gender identity and the sex they were assigned at birth. It’s about personal identity, psychology, and social/medical considerations, not the soul’s karmic path.

Shoin, so far what we learned from the Arizal is this: Rivka was a gilgul of Chava.  But there is more: In Sha’ar HaGilgulim (Hakdama 22 and 29), he writes this:  Rivka was a tikkun -rectification- for the damage Chava caused in the womb. Pshat is azoy: When Chava ate the forbidden, the tumah (impurity) of the nochosh entered not only her, but embedded itself in the future pregnancies of all womankind. And who removed that tumah? Rivka. How so? Thorough her stomach pain. When we read -in our parsha- “vayisroytzetzu habonim bekirba” that the children in her womb were quarreling, this infighting was the final battle between the tumah implanted by the snake and the kedusha implanted by Odom. In other words: Rivka’s pregnancy wasn’t uncomfortable; it was pelvic exorcism. Well, blow me down with a feather!

The snake implanted tumah into Chava? What’s up with that? How did the snake who but gave Chava a bite of forbidden fruit, implant impurity?  Was he up for it? And just how taka did Rivka rectify Chava’s sins? What exactly is the Arizal talking about when he states that tumah entered Chava? Shoin, let’s turn back the clock to Parshas Bereishis where avada you will recall learning -everyone remembers this part- the myseh where the nochosh (snake) somehow convinced Chava to eat from the Eitz Hada’as (Tree of Knowledge). And what did Chava do immediately after she was enlightened and after -according to some-she had a shtikel relationship with the snake itself? A relationship with what? Well, believe it or not, several medroshim, specifically the mystics, believe that Chava and the snake who was still upright back then -was he ever, if you chap- mamish had relations of some sort. What the means exactly, ver veyst! Has the Ois gone off the reservation? Perhaps, but not with this pshat because it’s mamish right of the medrish (Bereishis Rabbah 18:6) which tell us that the nochosh attempted marital relations with Chava. In fact, though not explicitly stated, according to some, the upright -if you chap- but not so upstanding nochosh did just that!  The heylige Zoihar (vol. I, fol. 55b-56a) and other kabbalistic texts discuss the concept of the “nochosh” (serpent) as a spiritual force that seeks to corrupt female souls. Some later kabbalists (medieval commentaries on the Zoihar) use allegorical language suggesting that Chava’s sin caused the conception of demonic forces, sometimes described as “mazikin” or “shedim.” In other words, that’s what she delivered as a result of this pregnancy. Back in Bereishis (4:25) we read this: “And Adam knew his wife again, and she bore a son and called his name Shais (Seth)…” In the text of the parsha which is avada very precise, there is no mention of demons, non-human children, or any unusual pregnancies. Chava gave birth to Kayin, Hevel, and then Shais (with other children implied later (see Bereishis 5:4) and any claims about demons or other beings are from later mystical or midrashic sources, not the plain text. That said, certain medieval mystical texts (some versions of Sefer HaTemunah, Sefer HaRazim, or obscure kabbalistic writings) make statements about Chava giving “birth to demons” before Shais.

What taka may have happened? We need to assume that these interpretations about Chava and the snake are but allegorical or symbolic: some texts taka say that before Shais, Chava’s spiritual mistake created forces of impurity, sometimes described as “demons,” which needed rectification in future generations. Shais is then born -130 years later- as the first fully rectified, spiritually aligned child, signaling a new stage of human spiritual development. One medrish suggests that during the 130-year time frame until Shais, Cava only gave birth to these demons. The bottom line: exactly what took place between Chava and the snake, ver veyst, and it can zicher appear like “pregnancy,” perhaps many of them. Ober, we need to chap that the language of “giving birth” in these mystical texts is metaphorical, representing the emergence of spiritual entities from sin. Why is that? Because in Kabbalah, “birth” doesn’t always refer to the physical womb, but to emanation or creation of a spiritual form. As well, we need to chap that the sources do not literally say she had sexual intercourse with the slithering snake though we are taught that back then, the snake -as mentioned above- stood upright and was seemingly capable of the act. The “impregnation” is symbolic — meaning that from the sin of the first woman came negative spiritual consequences (evil sparks, klippos, demonic tendencies). What all the means is above my pay grade. Veyter.

Says the heylige Toirah that Chava went and gave some of that forbidden fruit to her husband. Rashi will tell us that she did so out of fear. She was afraid that Odom, following her death, would seek out another woman. She was taka enlightened! In the past, we have talked about the jealousy of women and how they do crazy irrational things when jealousy takes over, and this week we learn that Chava was not just the first woman, she was also the first such woman. She did not want Odom with another woman, her eventual passing notwithstanding. Odom, being a man, was weak.  He partook of the forbidden fruit and shoin, both were cursed. He with death and struggles to make a living, and she with birthing pains and insane jealousy. Let’s also keep in mind that ever since Odom, men have enjoyed -very much so- in partaking of forbidden fruit, oy vey. Let’s not forget that woman was also cursed with long term memory; they don’t forget a thing.  The list goes on.

Nu, what to do and how to fix this mess? Shoin, along came Rivka whose job now was to untangle and rectify. And she did this how? Halt kup (pay attention), as it’s mamish so gishmak. Back in Bereishis, Chava fed her husband something forbidden, ober here in our parsha, along comes Rivka and with her devious plan to help her younger son outwit her older son, to prevent her husband Yitzchok from eating something forbidden. And what was that? The very food that Eisav had just hunted down and prepared at his father’s behest. Says Reb Targum Yoinoson azoy: the dish Eisav prepared was not kosher. Moreover, it was not slaughtered in accordance with the rules of the ‘not-yet-given-Toirah.’ Of course, you recall that our Ovois (forefathers) kept the heylige Toirah in its entirety. And it so happens that Targum Yoinoson will tell us that Eisav brought him dog food, say it’s not so.

The bottom lines: The mystical idea that Chava’s sin created “negative offspring” strengthens the idea that a later holy soul was needed to rectify it. Rivka’s mission was to repair Chava’s missteps and according to the mystics, she guides Yaakov’s actions, ensures proper blessings go to the right child, and prevents the perpetuation of spiritual corruption. In other words, the “demons” are part of the spiritual imbalance Rivka came to fix. The bottom line: Exactly what took place, ver veyst, but one thing is zicher: absent of any eye-witnesses besides the RBSO who chose not to share the intimate details of what went down between Chava and the snake, the imaginations of some of the famous mystics was mamish out of control. Let’s go veyter.

Lest you think that only Rivka was a gilgul, let’s close with this:  Yaakov’s story is further developed, we will find him deeply involved in the plot to outwit his older brother Eisav out of his birthright. Zicher you recall this famous myseh, everyone does. Ober how could honest Yaakov taka be involved in so nefarious a plot? Ober says the Zoihar and who had a better imagination that did he, azoy: it’s quite poshit (simple). It was Yaakov’s tafkid (his mission) to come down to earth to rectify the sins of Odom and his lovely wife Chava. They were enticed by the snake who used his cunning ways to bring them to sin. Therefore, Yaakov was sent down to use some of his own cunning (with help from his mother Rivka of course) to outwit his brother Eisav out of the birthright. Shoin, even-steven. It’s what the RBSO wanted and if the RBSO wanted that outcome, as He seemingly did, and for Yaakov to be the father of the B’nai Yisroel, He enabled Rivka along with Yaakov to cook up (pun intended) this givaldige plot. And it so happens that the Zoihar will tell us that Eisav represented the bad snake that needed to be rectified. Shoin the loop is closed. Rivka is the reincarnation of Chava, Yaakov came down to rectify the sin of Odom and Eisav was here so that through him losing the birthright, the snake too would be rectified, though erect he would never again be. He continues to slither and cause trouble ad hayoim hazeh (until today’s times).

Earlier we mentioned that because of the chicanery as plotted by Rivka and executed by Yaakov who snookered his older brother, he was now the proud owner of the birthright while Eisav was left seething and plotting revenge. Rivka had no choice but to send Yaakov out of the house and the city. She was avada concerned for his safety and was seemingly also concerned that he was still single.  Not just single but 63 years old and still single; yikes!  And, having seen the ethnicity of the women Eisav already married -two Chitite shiksas- Rivka was mamish tzibrochen that her son ‘married out’ and warned Yaakov not to marry a girl from Chiti.  Next, we will learn that after hearing Rivka’s instructions, Yitzchok spoke up and asked Yaakov not to marry any K’nany girls either. The next posik (Bereishis 28:7) tells us azoy: “and Yaakov obeyed his father and mother and went to Paddan-aram.” So happens that the Ois, a few months back mamish, came across a street named Padanaram while on a drive to CT and was taka wondering if this street has epes biblical connections.  Ober that for another day; let’s go veyter.

Ober what could Yaakov have been thinking when, after obeying his mother and having been blessed by his father, suddenly found himself kicked out of his own house and city?  He was mamish on the run. Was this his reward for ‘kibud Eim’ (honoring and obeying his mother?) Was this new life the manifestation of his father’s brochis? Not! His new reality was that of a fugitive; he was exiled from his mishpocho and heading to places unknown. Would he see them again? Moreover, Yaakov’s adventures as will be detailed from here until the end of Sefer Bereishis are mistama not what he had in mind when he heard his father promise him an abundance of spiritual and materialistic success.

Ober Raboyseyee and ladies, we have to chap that pshat is mistama azoy.  Only in looking back can one see that the journey was necessary. Yaakov’s journey was taka shver. There are zicher times when many of you feel like Yaakov. Ober we must keep in mind azoy: though one may find himself on a circuitous and perilous road filled with aggravation and embarrassment, it’s efsher part of the master plan, ver veyst. As to Yaakov, efsher it was only because he was on the run and only because he needed to escape from his brother, that he did propitiously somehow end up -where else but at the well- meeting the love of his life, Rochel and her older sister Leah. Let’s avada not forget Bilah and Zilpah. In the end he did marry all four. Each gave him children and twelve of them went on to become the fabulous holy shevotim (tribes). Avada we will have lots more to say about these twelve and their sister Dina, ober that for another parsha.

What’s taka the take-away from all this? Nu, for those seeking inspiration and hope, for those currently down on their luck, their lives, or marriages, or, whatever else, and see only darkness, this darkness may in reality be the beginning of the new dawn, the new light. Not always of course but let us not lose hope. When Yaakov set out from his parent’s home, he was on a journey and did not yet know what may lie ahead. It was a journey into the unknown; ober in the end, because he kept his faith -although he did taka make a deal with the RBSO- as we will learn in the upcoming parshas- he did lead a productive life, had a name change to Yisroel and we, his progeny, are all referred to as the B’nai Yisroel. Gishmak.

The takeaways? Are we allowed to not believe in gilgul? ABSOLUTELY. It’s totally kosher. Many gedolim (big big Sages, some even giants) did not believe in it. That list includes: The Rambam, Rav Saadia Gaon, Rav Sherira Gaon, The Son of a gun, The Meiri, The Abarbanel (sometimes), and Rav Hirsch. On the other hand, many big names did believe in gilgul and that list includes The Arizal, The Ramak, The Zoihar, The Vilna Gaon, the Ramchal, and Chassidus generally.

The final bottom line: If you don’t believe in reincarnation, that is a very kosher Jewish position, held by serious early sages -from the Gaonim straight down to the Rambam. Is gilgul min haToirah? Not! It’s not pshat, not medrish, not Mishna, and not  Gemora. It shows up much later in the mystical tradition. If you want to believe in it- Gezunderheit (be my guest, knock yourself out)!  The heylige Zoihar, the Arizal, and half of Chassidus will back you up. Want to say it’s bubbe mysehs? Also perfectly kosher as the Rambam, Saadia Gaon, and a few other heavyweights will be sitting next to you in Olam Habo, nodding in agreement.”

A gittin Shabbis!

The Heylige Oisvorfer Ruv

Yitz Grossman

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