September 7, 2025|י"ד אלול ה' אלפים תשפ"ה The Most Powerful Chinuch By Rabbi Jonathan Muskat

In the 1920s, Al Capone virtually owned Chicago. He was notorious for bootlegging, prostitution, and murder. His lawyer, “Easy Eddie,” was brilliant. Thanks to Eddie’s legal maneuvering, Capone avoided prison for years. Capone paid him handsomely: Eddie lived in a mansion the size of a city block, with every luxury.

Eddie enjoyed the high life, but he had one soft spot –  his son. He gave him everything money could buy and tried, despite his mob ties, to teach him right from wrong. Yet with all his wealth, there were two things Eddie couldn’t give his son: a good name and a good example.

Eventually, Eddie reached a painful decision. He would testify against Capone. He knew it would cost him dearly, but he wanted to leave his son the gift of integrity. 

The entire institution of ben sorer u’moreh – the wayward son who is executed for stealing meat and wine – seems almost impossible to grasp. Teenagers make plenty of mistakes; can we really believe this law was ever carried out? The Gemara itself says it never happened. Rabbi Yehuda explains it was impossible to fulfill the legal requirements. Rabbi Shimon adds it is inconceivable that parents would hand over their child. So why does the Torah present this law at all? Drosh v’kabel Sachar – to teach us. It warns us about how quickly youthful indulgence can lead to adult destruction, and it calls on us to be vigilant as parents and educators.

But Rabbi Yonatan pushes back: ani re’itiv v’yashavti al kivro – “I saw him, and I sat on his grave.” According to Rabbenu Bachya, Rabbi Yonatan wasn’t describing an actual trial but a child who fit the profile – impulsive, indulgent – who eventually became the criminal the Torah predicted. The debate is really about whether some children are irredeemable. Most sages insist no child is beyond hope. Parents and teachers must never give up. But Rabbi Yonatan insists: re’itiv v’yashavti al kivro – I have seen with my own eyes a wayward teenager who never turned his life around, and I sat on his grave. In other words, after his death, it became clear to all that he had become exactly what the Torah warned he would become. Rabbi Yonatan reminds us that in rare cases, even after all efforts, a child may not change. The question then becomes: what does it mean to truly “try”?

Here the Midrash adds a deeper layer. Why is ben sorer u’moreh placed right after the laws of the eishet yefat to’ar and the man with two wives? First, we encounter the case of the eishet yefat to’ar – the captive woman whom a soldier desires in battle. The Torah allows him to marry her, but only after a period of waiting and transition. Then, immediately following this, the Torah discusses the man with two wives – one beloved, one hated – and the laws of inheritance that arise from such a situation. And right after that comes the section about the ben sorer u’moreh, the rebellious child. 

Why is this sequence important? Because it tells a story. Because it is one story. A soldier loses control and marries a captive. Later he has two wives – one loved, one hated. Out of that conflict comes the wayward son, who also cannot control his impulses. Imagine the father rebuking his son for indulgence, only for the boy to answer: “Father, isn’t my very existence the result of your lack of control?” And the father has no reply.

This is not punishment – it is consequence. A child who cannot master himself often learned that from a parent who could not master himself. Yes, the father can do teshuva, but he cannot erase what his children saw. He cannot undo the model he gave them.

That is the sobering message of this sequence: eishet yefat to’ar, the hated wife, the wayward son. The Torah is teaching us that the most important thing a parent or educator can do is to be a role model. Children learn far more from who we are than from what we say. We can tell them to be honest, but if we cut corners, they will too. We can tell them to be respectful, but if we speak without kavod, they will copy us. We can tell them to control their desires, but if we fail to control ours, the lesson will not stick.

And we see this today, even in small, subtle ways. I’ve noticed not just in this community but in many communities that some fathers of teenage boys who never used to come to shul on Sunday mornings now show up alongside their sons. Maybe they didn’t make that effort before, but something changed. Perhaps consciously, perhaps unconsciously, they realized: if I want my child to grow in commitment, I need to model commitment. And of course, this truth applies far beyond davening. In every arena of life – chesed, Torah, honesty, respect – our children are watching us more than they are listening to us.

Teshuva can repair so much – but not the example we set once it has been absorbed. That becomes part of a child’s world. And so, the Torah’s message is clear: if we want children who can channel their impulses for good, we must show them how it is done. Because the most powerful chinuch does not come from what we say. It comes from how we live.

Eventually, Easy Eddie reached a painful decision. He would testify against Capone. He knew it would cost him dearly, but he wanted to leave his son the gift of integrity. Not long after, Easy Eddie was gunned down on a Chicago street.

Let me share with you a second story. The Second World War produced many heroes. One of them was Lieutenant Commander Butch O’Hare, a fighter pilot on the aircraft carrier Lexington in the South Pacific.

One day his squadron went out on a mission, but after takeoff he realized his fuel tank hadn’t been filled. Ordered back to the carrier, he turned around – only to spot a squadron of Japanese planes heading straight for the defenseless American fleet.

With no time to warn anyone and no squadron to back him up, Butch had only one choice: to attack alone. He dove straight into the formation, his guns blazing. Even after his ammunition ran out, he continued diving at the planes to scatter them. Finally, the enemy squadron veered off.

His gun camera later confirmed he had destroyed five enemy aircraft. On February 20, 1942, Butch O’Hare became the Navy’s first ace of World War II and the first naval aviator to win the Medal of Honor. A year later he was killed in combat at just 29.

Today, Chicago’s O’Hare Airport bears his name, and a statue and his Medal of Honor stand between Terminals 1 and 2. What do these two stories – the story of Easy Eddie and story of Butch O’Hare have to do with each other? Butch O’Hare was Easy Eddie’s son.

Butch O’Hare was Easy Eddie’s son. A man who once lived surrounded by corruption, who chose in the end to risk everything to leave his child a different kind of inheritance—not wealth, not status, but a good name and a good example. And from that gift of integrity emerged a hero whose courage saved countless lives, whose legacy is remembered to this day.

This is the Torah’s message. Ben sorer u’moreh is not about a child who was condemned – it’s about parents and teachers who must recognize the immeasurable impact they have. It is about realizing that who we are becomes who our children become. Our choices echo in the lives of those who look up to us.

As we approach the Yamim Nora’im, the season of teshuva, we are called not only to repair our relationship with God, but to ask: what impact am I having on others? What model am I providing – for my children, my students, my friends, my community?

Because the truth is, our greatest influence will not come from our words, our speeches, or even our lessons. It will come from the lives we live every single day. If we want the next generation to be strong, honest, compassionate, and faithful, then we must be strong, honest, compassionate, and faithful.

Teshuva is not only about who we are. It is about who we inspire others to become. And if we can rise to that challenge – if we can live as models of integrity and faith – then the legacy we leave will not only change our children. It can change the world.