In Parshas Toldos, we are first introduced to Yaakov and Esav. Their struggle with each other began even before their birth, as they pained their mother Rivka while still in her womb. At the beginning of the parsha, before we really even know a great deal about the twins, the pasuk states that Yitzchak loved Esav and that Rivka loved Yaakov. That’s not to say that each parent didn’t love the other child as well, but the Torah emphasizes that Yitzchak had an affinity to Esav, while Rivka had an affinity to Yaakov. From a young age, we are taught the events that follow between Yaakov and Esav. Esav returns home rather peckish after a strenuous day in the field. His younger brother was in the kitchen preparing food, which enticed him tremendously. Yaakov, as we know, only acquiesces to feed his brother on the condition that he, the younger brother, receive the Bechora blessing from their father. A strange trade off, no? Esav, as ravenously hungry as he was, agrees to these terms, and the deal is done.

I have always been curious as to why Yitzchak felt more of a connection to Esav than he did to Yaakov. Didn’t he know Esav was a rasha and Yaakov was a tzaddik? He wasn’t a random passerby who didn’t know the stories of the brothers and what they were doing with their lives. He’s their father! Even though Esav is the elder of the two, Yitzchak could’ve given Yaakov the blessing and blessed Esav with something else, which he ultimately did anyway!

So why did Yitzchak want to give the bracha of Bechora to Esav? Surely Yitzchak knew that Yaakov was an “ish tam” and that Esav was “yodeah tzayid.” The Chasam Sofer’s take on this conundrum is one that I found very interesting. He posits that Yitzchak had envisioned a grand partnership between the twins. In his mind, Esav and Yaakov were supposed to function like Yissachar and Zevulun. Yaakov would learn and support Esav spiritually and Esav would support Yaakov’s needs. It was precisely for this reason that despite Yaakov trading for the Bechora and being more righteous than his brother, Yitzchak was so intent on giving Esav the Bechora. Yitzchak Avinu still held to the belief that this model of working together could be achieved. The blessing given states that Hashem should give him from the dew of the Heavens and the fat of the land, while also being privy to an abundance of grain and wine. This was all supposed to go to Esav in order to support himself as well as Yaakov. While Esav is indeed blessed in the Parsha, he did not receive the Bechora, the blessing he traded away so eagerly yet eventually came to cash in on.

It’s written in Tehillim (133) “Hinei mah tov umah naim sheves achim gam yachad. How good and how pleasant it is, brothers sitting together.” (It was actually written by David HaMelech before it was a Miami Boys Choir song…). Rivka may have known that this was not to be, and sent Yaakov away as soon as he was blessed with the Bechora. But for Yitzchak, it was a dream that he still held onto of what could have been.