03 Nov THE JUDGE WHO BELIEVES IN ME

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 G-d, 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
you shall justice ,Justice “ֶ,צֶֶדֶק ֶצֶֶדֶק ִּתְּרְֹּדּף
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:
ִּכּי יְְַדַעְְִּתּוי- ְלְַמַַעַן אֲֲֶׁרש-ׁ יְְצֶַַּוּה ֶאֶת ּ-בָָּנָוי ְו ְֶאֶת- ֵּבּיתֹו
אֲַַחֲרָָוי- ְו ְ ְמְׁשָׁוּר רֶּדְֶֶּך- ה׳ לַַעֲֲׂשֹות- צְְ ָדָקָָה ׁשְִׁמִוָּּפּט
“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: ְׂשֹׂמֹאל
should hand left The -דֹּחוָָה ְו ְיִָָמִין ְמְ ָקָרֶֶֶבֶת
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.
is great , ַרַּבָּה אֱֱוּמָנָתֶֶָך say we morning Every
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 נומאתיך” – 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.