“Quitters Always Finish First” – The Brutal Truth About Spiritual Growth (Parsha Pearls: Toldos) 5786

Parshas Toldos is the ultimate masterclass in parenting, love, perseverance, and the eternal tug-of-war between heaven and earth. When Rivka feels her twins fighting in the womb, she is terrified that she is carrying one confused child who is pulled toward both holiness and idolatry. The prophet calms her with the shocking news: “Shnei goyim b’vitnech – two nations are in your womb.” Instead of despairing, she is relieved. Why? Because, as Rabbi Wolbe explains, “the benefit and greatness of Yaakov is so immense that it will supersede all the negative that she will ever experience from Esav.” One pure Yaakov is worth more than all the damage a thousand Esavs can do.

The Torah then paints a seemingly troubling picture: “Isaac loved Esav because he put game in his mouth, but Rivka loved Yaakov.” How can holy parents play favorites? The answer redefines love itself: “Love is not finding similarities — love is seeing the potential in the other person and connecting to that.” Isaac gazed at wild, powerful Esav and thought, “If this explosive energy is ever channeled for good, he could move mountains.” Rivka looked at quiet, tent-dwelling Yaakov and saw pure, undiluted holiness already shining. Both parents loved both sons — they simply poured their energy into the child whose hidden potential moved them the most. This becomes the model for all healthy parenting and marriage: every child is your favorite — favorite scholar, favorite artist, favorite comedian, favorite mensch — because “each one is uniquely different… you’re not comparing apples to apples, you’re comparing apples to oranges to bananas.”

For 63 long years Yaakov lives in his wicked brother’s shadow. Esav hunts, flatters, and cleverly asks questions like “How do you tithe salt?” just to appear pious and win Isaac’s heart. Yaakov, meanwhile, clings only to the “heel” of spirituality — always second place, always doubting, always wondering, “Maybe my father is right and I’m wrong.” Yet he never once compromises. At 63 he finally cooks the lentil stew that wins the blessings, proving that “spiritual growth is always at the heel — slow, painful, and full of doubt — but the tzaddik never quits.” As Rabbi Wolbe powerfully declares: “Quitters always finish first. If you want to win, you can’t quit — ever.” And again: “The natural state of a tzaddik is to fall seven times… but the falling is not what we emphasize — it’s the getting back up.”

The parsha ends with two beautiful side lessons. First, Eliezer (from the cursed lineage of Canaan) is rejected as a match for Isaac, yet when he remains loyally devoted to Avraham despite the insult, Hashem rewards him with kfitzas haderech — miraculous instant travel reserved only for the righteous. Loyalty and perseverance turn even a “cursed” person into a tzaddik. Second, the same dynamic of “investing in the child who needs it most” repeats with Yaakov and Yosef: Yaakov favors Yosef not out of nepotism, but because he sees the unimaginable trials awaiting him in Egypt and knows, “This one is going to need extra love to survive and triumph.”

_____________
This episode of the Parsha Review Podcast is dedicated in honor of Lenny & Teresa Friedman

• Download & Print the Parsha Review Notes:
  https://drive.google.com/drive/folders/1ncaRyoH5iJmGGoMZs9y82Hz2ofViVouv?usp=sharing

Recorded at TORCH Meyerland in the Levin Family Studios (B) to a live audience on November 25, 2025, in Houston, Texas.
Released as Podcast on December 3, 2025

_____________
Subscribe: 

• Apple Podcasts (https://podcasts.apple.com/us/podcast/parsha-review-podcast-rabbi-aryeh-wolbe/id1651930083)
• Spotify (https://open.spotify.com/show/22lv1kXJob5ZNLaAl6CHTQ) to stay inspired! 

Share your questions at [e-mail] or visit torchweb.org for more Torah content.  
_____________

About the Host:
Rabbi Aryeh Wolbe, Director of TORCH in Houston, brings decades of Torah scholarship to guide listeners in applying Jewish wisdom to daily life.  To directly send your questions, comments, and feedback: [e-mail]
_____________

Support Our Mission:
Help us share Jewish wisdom globally by sponsoring an episode at torchweb.org. Your support makes a difference!
_____________
Subscribe and Listen to other podcasts by .css-j9qmi7{display:-webkit-box;display:-webkit-flex;display:-ms-flexbox;display:flex;-webkit-flex-direction:row;-ms-flex-direction:row;flex-direction:row;font-weight:700;margin-bottom:1rem;margin-top:2.8rem;width:100%;-webkit-box-pack:start;-ms-flex-pack:start;-webkit-justify-content:start;justify-content:start;padding-left:5rem;}@media only screen and (max-width: 599px){.css-j9qmi7{padding-left:0;-webkit-box-pack:center;-ms-flex-pack:center;-webkit-justify-content:center;justify-content:center;}}.css-j9qmi7 svg{fill:#27292D;}.css-j9qmi7 .eagfbvw0{-webkit-align-items:center;-webkit-box-align:center;-ms-flex-align:center;align-items:center;color:#27292D;}