Family D'var Torah Parshas Vayeshev: Paving the Road for the Next Generation

By R' Yechiel and Nati Del Castillo

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An interesting phenomenon occurs in this week’s parashah: the abundance of the letter vav. Nearly every pasuk begins with a vav, symbolizing connection and continuity throughout the narrative.

In Hebrew, the word vav means “hook” or “connector,” like the hooks used to join the curtains of the Mishkan and the Beit HaMikdash. By beginning almost every pasuk with a vav, the Torah teaches that every detail in the parashah is interconnected and essential to the final outcome of the story of Yosef and his brothers. Events that appear disparate, painful, or even tragic at the time are all part of a larger, divinely orchestrated plan. The unbroken flow of the narrative emphasizes that the episodes in Vayeishev: Yosef’s dreams, his sale into slavery, the story of Yehudah and Tamar, and Yosef’s descent into Potiphar’s house are not random. Rather, they form a continuous sequence leading to the Jewish people’s descent into Egypt, in fulfillment of Hashem’s will and prophecies.

Our forefather Yaakov showed special favor to his son Yosef, the firstborn of his beloved wife Rachel. Rashi (Bereishis 37:3) explains that Yaakov taught Yosef all the Torah he had learned in the yeshivah of Shem and Ever, and he purchased fine wool to make Yosef a special coat. This favoritism stirred jealousy among the brothers, which eventually turned into hatred and led them to sell Yosef into slavery. The long-term result of this act was the exile and enslavement of the Jewish people for hundreds of years.

Chazal derive from this story a powerful lesson about parenting. The Gemara (Shabbat 10b) teaches that it is improper to show favoritism to one child over another. As the Talmud states: “Because of the favoritism that Yaakov showed to Yosef by purchasing him fine wool weighing two sela’im, his brothers became jealous, and this caused our forefathers to descend to Egypt.”

Our sages further teach, in Midrash Rabbah, the Zohar, and other sources, how remarkably similar Yaakov and Yosef were.

The Torah states: “These are the generations of Yaakov: Yosef was seventeen years old…” (37:2).

Should the verse not have said, “These are the generations of Yaakov: Reuven, Shimon, Levi…”? Why single out Yosef? Because everything that happened to Yaakov also happened to Yosef.

Just as Yaakov was born circumcised, so too was Yosef. As Yaakov’s mother was infertile, so was Yosef’s. As Yaakov’s mother experienced difficulty in childbirth, so did Yosef’s. As Yaakov’s mother bore two sons, so did Yosef’s. As Yaakov was hated by his brother and pursued for his life, so was Yosef hated by his brothers and nearly killed by them. Yaakov was a shepherd, and Yosef was a shepherd. Yaakov was persecuted, and Yosef was persecuted. Yaakov was exiled from Eretz Yisrael, and Yosef was exiled from the Land.

Yaakov married outside the Land and fathered children outside the Land; so did Yosef. Yaakov was escorted by angels, and Yosef was escorted by angels. Yaakov rose to greatness through a dream, and Yosef rose to greatness through dreams. The house of Yaakov’s father-in-law was blessed because of him, and the house of Yosef’s master was blessed because of him. Yaakov descended to Egypt, and Yosef descended to Egypt. Yaakov ended a famine, and Yosef ended a famine. Yaakov adjured his children, and Yosef adjured his brothers. Yaakov died in Egypt, and Yosef died in Egypt. Yaakov was embalmed, and Yosef was embalmed. The bones of Yaakov were brought back to Eretz Yisrael, and the bones of Yosef were brought back as well.

Yaakov fathered tribes, and Yosef fathered tribes. Yaakov was separated from his father for 22 years, and Yosef was separated from his father for 22 years. Yaakov was indentured because of a woman, and Yosef was imprisoned because of a woman. Yaakov supported Yosef for 17 years, and Yosef supported Yaakov for 17 years.

I want to focus for a moment on Yosef’s age. Yosef was only seventeen years old when he was thrust into the most morally depraved society of that era. How was he able to withstand such intense nisyonos? How was he able not only to survive, but to build a strong, frum family in Mitzrayim? These trials were designed to strengthen our forefathers and their descendants, to succeed and ultimately fulfill HaKadosh Baruch Hu’s plan for the Jewish people. Their resilience became part of our Jewish DNA.

In Sefer Mishlei (22:6), Shlomo HaMelech teaches: “Train a youth according to his way; even when he grows old, he will not depart from it.” In just a few words, this oft-quoted pasuk provides a timeless guide to chinuch. Rabbeinu Yonah explains that young people lack the maturity and wisdom to guide themselves properly; therefore, they must be guided while their character is still malleable and receptive to change. One must not delay education until later years, when habits are harder to reshape. Rabbeinu Yonah adds that true education is a gradual process, advancing patiently from stage to stage.

Yosef was trained to see the world not through physical eyes alone, but through spiritual eyes. His perspective was firmly rooted in the Torah he learned from his father, Yaakov. Torah, our rock, shield, and protection, empowers us to face life’s challenges without being overwhelmed by what we see on the surface. Instead, it teaches us to trust that just as our forefathers endured their trials, we too can overcome ours. This spiritual vision, however, can only be sustained if we continuously nourish our souls with heavenly food.

We are truly blessed to be part of the Yesodei Yisrael family, with Rabbeim who pour themselves into each child, partnering with parents to train, prepare, and mold our children in Hashem’s ways through Torah. Let us carry forward the message of this week’s parashah: continuity in Torah learning is the antidote to the yetzer hara and its relentless attempts to pull us away from Hashem’s plan for our lives.

Good Shabbos.

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The Del Castillo family made Aliyah from St. Louis, Missouri in 2023 and currently resides in the Neve Shamir neighborhood of Ramat Beit Shemesh. Their family story is both unique and inspiring. Originally from Panama, they immigrated to the United States in 1981. In 1983, Yechiel Del Castillo enlisted in the United States Navy, where he served as a combat medic until 2008, including four deployments to the Persian Gulf.

Following his military service, R’ Yechiel spent an additional ten years in military civil service, supporting the U.S. Army, Navy, and Air Force. In 2021, the Del Castillo family completed their journey by converting to Judaism, and they now continue to build a life of Torah and community in Eretz Yisrael.

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