November 2, 2026|כ"ב חשון ה' אלפים תשפ"ז The Judge Who Believes in Me
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In 2012, a young woman named Alexa, struggling with drug addiction, stood before a federal judge in New York awaiting sentencing. The judge sentenced her to 18 months in prison. He told her it was one of the hardest sentencing decisions he had ever made but also told her something she would never forget: He said he believed in her. He believed she could overcome her struggles and had a bright future ahead of her.
Think about that. He was sending her to prison while telling her he believed in her future. He was holding her accountable without giving up on her. Alexa served her sentence, turned her life around, earned a master's degree, secured a respected position in New York State government, and built a family.
Last week, when the judge passed away, she wrote a remarkable tribute: "He changed my life. My time in prison is exactly what I needed and I was indeed able to have a bright future." She added, "I will never forget the impact he made on my life and the tough love that was shown to me."
The judge was the Honorable Alvin K. Hellerstein, my brother-in-law's father, who passed away at 92. Al, as I knew him, served for nearly three decades as a federal judge in the Southern District of New York. He presided over many consequential cases, including high-profile litigation arising from September 11 and the recent criminal case against Venezuelan leader Nicolas Maduro. He was a respected legal mind, accomplished jurist, and was well-regarded among his peers and the lawyers who went before him. But the lesson I want to share isn't about his distinguished career. It is about something he understood that we all need to learn.
Sometimes love means saying no. Sometimes caring means holding someone accountable. And sometimes believing in someone means refusing to give up on what they can become.
I had the privilege of knowing Al for many years as family. He was kind, thoughtful, and generous with compliments. He made people feel appreciated but was also honest with constructive feedback. His praise meant something because you knew his honesty was genuine. Above all, Al loved his family. For all his professional accomplishments, they were at the center of his life.
A few years ago, we interviewed Al on our Behind the Bima podcast. Asked how his Jewish values influenced his work, he explained that when sentencing someone, he reminded himself that the defendant was a person created by God, just as he was. That person may have done something terrible, but that didn't make him a terrible person. In his words, "I'm punishing him not as a bad person—because he's not—but for the bad things he does."
What a powerful distinction. We can reject someone's behavior without rejecting the person, be disappointed in what someone has done without losing faith in who they can become. Al shared that he intentionally scheduled sentencing hearings on Friday mornings so he would have Shabbos to reflect on them. Had he been too severe? Too lenient? Too compassionate? He admitted he never felt completely confident he had gotten the punishment exactly right. Taking away someone's freedom was an awesome responsibility, and it weighed heavily on him.
Displayed in his chambers were the words צֶדֶק צֶדֶק תִּרְדֹּף, "Justice, justice shall you pursue." Al explained his favorite interpretation of the repetition. We don't always know where justice is. We must pursue it, search for it, and never assume that having authority means automatically knowing what is right.
There is something meaningful about Al's Hebrew name, Avraham. We associate Avraham Avinu with chesed, his open tent, welcoming strangers, caring for others. But his legacy wasn't chesed alone. In Parshas Vayeira, Hashem explains why He chose Avraham:
כִּי יְדַעְתִּיו לְמַעַן אֲשֶׁר יְצַוֶּה אֶת בָּנָיו וְאֶת בֵּיתוֹ אַחֲרָיו וְשָׁמְרוּ דֶּרֶךְ ה׳ לַעֲשׂוֹת צְדָקָה וּמִשְׁפָּט
"For I have known him, because he will command his children and his household after him, that they shall keep the way of Hashem, to do righteousness and justice." (Bereishis 18:19)
Avraham understood what genuine love demands. The way of Hashem is tzedakah u'mishpat, kindness and justice together. Chesed without mishpat runs the risk of turning into enabling. Mishpat without chesed can become cruelty. We need both.
Al understood that balance. He could praise someone while offering criticism, encourage someone while challenging them to improve, sentence Alexa to prison while telling her he believed in her.
This is a lesson for every parent, spouse, teacher, and friend. We too often confuse love with approval, compassion with accommodation, and kindness with giving people what they want. We fear that boundaries, consequences, or saying no will damage relationships. But sometimes protecting people from the consequences of their choices deprives them of the opportunity to grow.
The Gemara (Sotah 47a) teaches: לְעוֹלָם תְּהֵא שְׂמֹאל דּוֹחָה וְיָמִין מְקָרֶבֶת The left hand should push away while the right hand draws close. The Kotzker Rebbe offers a beautiful insight. Imagine pushing someone's shoulder with your left hand while pulling them toward you with your right. What happens? You turn the person around. That is the goal. Not to reject someone, but to redirect them. Not to push them away, but to help them change direction. Discipline isn't punishment for its own sake. It is an expression of our belief in someone's ability to grow.
And notice it is the weaker left hand that pushes away while the stronger right hand draws close. Our love must be stronger than our discipline, our encouragement greater than our criticism. Tough love is never an excuse for anger, harshness, or control. Not every mistake requires punishment. But genuine love includes expectations, boundaries, and accountability, always accompanied by the reassurance that we believe in the person.
And there is another relationship where this lesson is especially important. Our relationship with Hashem, Who is the ultimate Judge, but also our Av HaRachaman, our compassionate Father. Being on the receiving end of His love doesn't mean He always gives us what we want or spares us disappointment and pain.
Sometimes we find ourselves in circumstances that feel like a prison, trapped by challenges we didn't choose and cannot seem to escape. We daven for the doors to open, but sometimes they remain closed. We wonder, if Hashem loves me, why am I here? Why doesn't He let me out?
Sometimes love means giving us what we need, not what we want. Sometimes the doors that close and the limitations we experience may be part of a greater plan for our growth, even when we cannot see it.
Of course, we cannot pretend to know why Hashem brings particular challenges into our lives. We should never tell someone suffering that their pain is deserved or that we know why it is happening. But emunah means believing that even when we cannot understand His judgment, we can trust His love.
That is what moves me most about Alexa's story. Al didn't simply reach the appropriate legal determination, sentence her, and walk away. He made sure to tell her he believed in her, that she could overcome her struggles, that she had a future.
Perhaps that is what we need to hear from the ultimate Judge as well. When life doesn't go as planned, when we feel stuck or overwhelmed, we must remember that the Judge who has placed us there is also our Father. He hasn't abandoned us, stopped loving us, or given up on us.
Every morning we say רַבָּה אֱמוּנָתֶךָ, great is Your faithfulness. The Chassidic masters offer a beautiful interpretation. While expressing daily gratitude for the gift of our life is certainly a reflection of our own emunah, the word we use when addressing Hashem is אמונתיך – “your faith.” Not only do we have emunah in Hashem, but Hashem has emunah in us. He returns our neshama each morning because He believes in our potential and what we can still accomplish. Every morning, Hashem is telling us what Al told Alexa. I believe in you. You can overcome your struggles. You have a future. You are not defined by your mistakes or circumstances.
Alexa eventually recognized that what felt like the end of her future became the beginning of a new one. We aren't always given that clarity in this world. Not every painful experience produces an outcome we can identify or appreciate. But Hashem's love remains present even when His plan is hidden.
I am grateful to have known Al, learned from him, and been part of his extended family. May we learn from his example to practice tough love when needed, always making sure those we love know we believe in them.
And when we feel confined by life's challenges, may we remember that the ultimate Judge is also our loving Father. His tough love is still love, and even when we struggle to believe in ourselves, He never stops believing in us.
Sometimes the Judge who says no is the very One who believes in us most.