Shanah Tovah! A Jewish Take on January 1

The streets beyond the shtetl were loud with music blaring and drunken laughter echoing into the frozen night. Fireworks shattered the darkness. It was a night of noise and escape, of people losing themselves in revelry.

Inside the Beit Midrash, the chasidim of the Ohev Yisrael of Apta sat hunched over their books, trying to shut out the chaos beyond the frost-covered windows. But the noise pressed inward until suddenly the tzaddik himself entered. Without a word, the Ohev Yisrael walked to the window and opened it slightly, allowing the commotion of the street to rush in. The chasidim were startled. Why invite the impurity of the outside world into their sanctuary? The Rebbe stood still, eyes half-closed, smiling, as if listening for something beneath the chaos. After a long pause, he gently closed the window and turned to his students.

“Do you hear how they celebrate? This is how the nations begin their year – with noise, confusion, intoxication, escape. And look at us. When a Jew begins the year, he trembles. He prepares for a full month with selichot, with the wake-up call of the shofar. He pours himself into teshuvah, tefillah, and tzedakah. With awe, he crowns the King and steps into the Yamim Nora’im.”

Then he added, “When you hear their shouting, let it remind you of who you are.”

Our calendar, our rhythm, our spiritual reset is on Rosh Hashanah. Judaism does not need January 1 to define renewal. And yet, our tradition refuses to waste a moment. We can identify a Jewish soul within January 1.

There are several rabbinic personalities who acknowledged that the secular New Year has a spiritual side. The chasidic rabbi, the Ba’al Ha-Yeshuot, would bless people with a good year even on the civil New Year, noting with gentle humor that when God contrasts the way the nations mark their year with the way Jews approach Rosh Hashanah, it brings us added merit. Likewise, Rabbi Menachem Mendel Schneerson, once wished a follower “Happy New Year” on January 1. He said this was the practice of Rabbi Levi Yitzchak of Berditchev, who explained, “When it comes to blessing, every time is appropriate.”

Rabbi Nissan Mindel, the personal secretary of the Lubavitcher Rebbe, was present in the Rebbe’s room on the night of December 31. When midnight arrived, the Rebbe glanced at his watch and wished him, “Happy New Year.” Upon seeing Rabbi Mindel’s expression of surprise, the Rebbe responded simply by quoting Tehillim (87:6): “Hashem shall take notice based on the recording of the nations.” God, too, takes note of how the broader world marks time.

The Rebbe shared this idea on another occasion. On December 31, 1989, while distributing his famous dollars, he told one of the recipients in English, “This will give you a happy year.”

There is wisdom about the infinite power of blessings, but also boundaries for how a Jew engages with the outside world.

Rabbi Norman Lamm was once asked about attending a New Year’s Eve dance. His response was classic and precise:

1. It is not technically prohibited.
2. Not everything permissible is advisable.
3. A better use of funds might be to donate the cost of the ticket towards organizing an evening of Torah study instead.

That is the Jewish approach in a nutshell: discernment without disengagement. Take note of the outside world and channel it towards a higher purpose. The world is excited as we turn the calendar; we should be excited as well.

January 1 is not ours, but it is there. And Judaism has always known how to take what exists in the world and redirect it toward purpose.

My understanding of the Jewish take on January 1 is not that it becomes sacred, but that it becomes usable. It has come to represent movement - forward motion, momentum, and the human desire to turn a page. And there is nothing more Jewish than refusing to let that impulse go to waste.

At a time when our community and our people face so many challenges, we need every legitimate opportunity to recommit to our values, our responsibilities, and our mission. While the world resets resolutions that often fade by February, we can double down on what already defines us, infusing it with new vitality, energy, passion, and enthusiasm.

So, yes, remember to write “2026” on your checks (for those who still write checks). But more importantly, let us take advantage of this moment when the world pauses and starts again. Not because January 1 is Jewish - but because Jews know how to move forward.

And for that opportunity, we can sincerely wish one another: Shanah Tovah!

Trusting Pilots & Having Skin in the Game

We do something curious when boarding an airplane.

Most of us have no idea who the pilot is. We don’t ask how many hours they’ve flown, where they trained, or whether they passed their last simulator test. We glance at the uniform, hear a calm voice over the intercom, buckle up - and entrust our lives to a total stranger.

Yet when it comes to choosing a doctor, we behave very differently. We research credentials, read reviews, ask around, want second and third opinions. We want to know everything.

Why the difference?

It isn’t because flying is less dangerous than medicine. It’s because the pilot is on the plane with us. The pilot has skin in the game.

If something goes wrong, the pilot doesn’t walk away. They go down with us. That shared fate generates a deep, instinctive trust. The doctor, no matter how skilled or compassionate, does not share that same immediate risk. If a procedure fails, the patient bears the consequences - not the physician. And so, we are more wary.

The Torah understood this long before behavioral economics gave it a name.

When Yosef demands that Binyamin be brought down to Egypt, Yaakov is paralyzed with fear. He has already lost Yosef. Losing Binyamin would be unbearable. Reuven steps forward with an offer that sounds dramatic and sincere: “You may kill my two sons if I do not bring him back to you.” (Bereishit 42:37)

At first glance, Reuven seems heroic. He is willing to pay the ultimate price. Yet, Yaakov rejects him outright. Why?  Because Reuven’s offer is not only ineffective but foolish. What comfort would it bring Yaakov to lose Binyamin and two grandsons? How does multiplying tragedy inspire trust?

Reuven’s pledge, though emotional, costs Yaakov everything and costs Reuven very little in the moment. It is a symbolic sacrifice, not a personal one.

Then Yehuda steps forward: “I will personally guarantee him. From my hand you may demand him. If I do not bring him back…I will bear the blame forever.” (Bereishit 43:9)

No theatrics. No collateral damage. Just responsibility. Yehuda does not offer someone else’s life. He offers himself - his future, his standing, his identity. He puts his own life, reputation, and destiny on the line.

And Yaakov immediately accepts. Because Yehuda has skin in the game.

The Netziv explains that Yehuda’s defining strength is achrayut, personal responsibility. Leadership is not about grand gestures or eloquent promises. It is about standing in the blast radius when things go wrong. Reuven’s offer says: “If I fail, others will suffer.” Yehuda’s guarantee says: “If I fail, I will suffer.”

That difference changes everything.

It is no accident that Yehuda becomes the progenitor of Jewish leadership and kingship. A king does not rule from safety. A leader does not outsource risk. True leadership requires shared fate.

It is interesting to note that Yehuda is also the first person to admit his mistake. When confronted by Tamar after accusing her of committing adultery and deserving of death, she did not blame others. She simply proclaimed that the father of her child was the owner of the “signet, and the cord, and the staff.” Yehuda immediately realized the situation – and he acknowledged the truth. “Tzadka mimeni – She is more righteous than me.” (Bereishit 38:26)

Yosef is known as the tzaddik, righteous one, for all he accomplishes, but the descendants of Yehuda earn the kingship for owning up and taking responsibility.

This principle matters far beyond the pages of Bereishit. If we want to influence a community, an institution, or even a family, we cannot stand on the sidelines issuing critiques and suggestions. People instinctively ask - often without realizing it: What does this cost you? What are you risking? What do you lose if this fails?

Ideas without investment rarely move people. Passion without personal stake rings hollow. If we want to change a culture, improve a school, strengthen a shul, or heal a relationship, we must show that we are not merely offering opinions - we are sharing consequences. That is when trust is born. That is when leadership emerges. That is when people listen.

Yaakov trusted Yehuda for the same reason we trust a pilot: because when someone is willing to go down with the plane, we believe they will do everything in their power to keep it in the air.

And that, the Torah teaches us, is what it means to matter.

The Chanukah Light Can Dispel Any Darkness

Banu chosech l’gareish, beyadeinu ohr va'esh
Kol echad hu ohr katan, v'chulanu ohr eitan
Surah choshech hal’ah sh'chor. Surah mipnei haor!

We come to chase away the darkness.In our hands are light and fire.
Each individual light is small, but together – our light is invincible.
Fight the darkness, chase away the blackness! Victory will be achieved because of the light!

This classic Israeli Chanukah song written in 1960 by Sara Levi-Tanai captures the essence of Chanukah: Jewish light dispels any darkness.

Over the past week, we were reminded of just how thick darkness can feel. On Sunday, the joy of Chanukah was shattered by the murderous attack in Australia. This horrific event amplified the darkness Jews have been feeling and heightened attention to vandalism of menorahs around the world, Jews attacked on subways and on the streets, and murders in Brookline, MA and Brown University.

At the same time, the light of Chanukah cannot be stopped.

Last Thursday, the IDF released video of hostages celebrating Chanukah in Hamas tunnels on the first night of Chanukah, December 8, 2023. Ori Danino is seen lighting a makeshift menorah with fellow captives Eden Yerushalmi, Almog Sarusi, Hersh Goldberg-Polin, Carmel Gat, and Alex Lobanov looking on. The group, who were later called “The Beautiful Six,” were executed in August 2024 as Israeli troops approached, and their bodies were discovered just two days later.

The group is heard reciting the Shehechiyanu, thanking God for “granting us life.” Later in the clip, one of the hostages is heard joking, “Where are the sufganiyot?” Hersh responded, “We’re waiting for Roladin in Israel,” referring to the bakery known for making all sorts of fancy donuts during the Chanukah season.

The hostages’ voices can be heard as they sing Chanukah songs and discuss religious differences in their upbringings and lives. While singing “Maoz Tzur,” Ori and Hersh sing the additional, lesser known five stanzas. Someone in the background asks, “Why so many verses?” “It’s describing all of the enemies who tried killing us over history,” replies Hersh. “Well, now we have to add another verse,” retorts Eden.

In the tunnels of Gaza…

Nothing stops the light. The hostages even discussed this.

In the footage, Hersh says lighting in the tunnels reminds him of the famous photo of the lit Chanukah candles in Nazi Germany. That picture was taken by the Posner family in Kiel, Germany in 1931. It shows their menorah on their windowsill, with a Nazi flag in the background on the building across the street. On the back of that old photo, Rachel Posner wrote a short poem:

‘Death to Judah,’ so the flag says. ‘Judah will live forever,’ so the light answers.

The hostages reciting Shehechiyanu recalls a story in Dr. Yaffa Eliach’s Hasidic Tales of the Holocaust. On the first night of Chanukah in Bergen Belsen, inmates crowded to watch the Bluzhever Rebbe kindle the makeshift lights. After reciting the first two berachot, he paused for a long moment, looked around, and only then recited Shehechiyanu.

A secular Bundist Jew who was present chided the rabbi, “How can you say Shehechiyanu here? How can you thank God for allowing us to live HERE?!?” The Rebbe responded:

“You are a hundred percent right. When I reached the third blessing, I also hesitated and asked myself, what should I do with this blessing? I turned my head to ask the Rabbi of Zaner and other distinguished rabbis who were standing near me, if indeed I should recite Shehechiyanu. But as I turned my head, I noticed that behind me stood a large crowd of living Jews, their faces expressing faith and devotion…I said to myself, if God has such a nation that at times like these stand and listen to the Chanukah blessings, if, indeed, I was blessed to see such a people with so much faith and fervor, then I am under a special obligation to recite the third blessing of Shehechiyanu.”

God has such a nation. Jews lighting in Bergen Belsen. Jews lighting in Hamas tunnels. Jews lighting to counter the darkness of terror, murder, and hate.

"Gvald, Yidn! Zayt zikh nit m’yayish! Jews don't give in to despair!" These words were the rallying cry of the Warsaw Ghetto Uprising in 1943. We never despair because we know the light will win.

Despite the darkness of Hamas in Gaza or Nazis in Germany or Islamist terrorists in Australia, Jewish light shines on. Jews celebrate Chanukah. Jews persevere. Jews thrive. Jews fight back. Our obstacles are setbacks, not defeats. Even when there is death, there will be life. Even when there is darkness, there will be light.

Banu chosech l’gareish. We are here to chase away the darkness armed with the light that, with God’s help, ensures our victory.

Pass or Take the Shot; See or Be Seen?

On January 6, 2007, a young basketball star named LeBron James scored in double digits.

Nothing unusual about that - except that he would go on to do it again. And again. And again. For the next 1,297 consecutive games, over the span of 18 years, LeBron James scored at least ten points in every single game he played. It became the longest double-digit scoring streak in NBA history - so massive that you would need to combine the next 11 active players just to catch him.

And then, last Thursday night, it ended. LeBron scored only eight points.

The Lakers were in a tight game against the Toronto Raptors. In the final possession, LeBron had the ball. He could have taken the shot, possibly extended the streak and maybe even winning the game himself. Instead, he found Rui Hachimura in the corner, who hit a three-pointer. Lakers win 123-120!

After the game, LeBron was asked for his thoughts about the streak ending. He answered with one word: “None.” Why? “We won.” He added that this was a career highlight and said, “I’m going to show my son this box score.”

"He's such an unselfish player," Lakers center Jake LaRavia said. "He had the opportunity, but because of the player he is and just who he is as a person, he made the unselfish play, passed it to Rui and we won the game."

LeBron had a streak that defined individual greatness. But in the defining moment, when the choice was “me” or to see the other, he chose to see.

We need to be looking for the “open man.” That’s how we win. We need to see.

Rabbi Kenneth Brander, the head of Ohr Torah Stone in Israel, discusses the Talmud (Shabbat 22a) connecting the laws of Chanukah lights with the story of Yosef in the pit.

Chanukah lights must be placed low enough to be seen because the mitzvah is about visibility. Immediately afterward, the Talmud recalls how Yosef’s brothers failed to see him. They ignored his cries, overlooked his danger, and allowed their own jealousy to blind them to his humanity. The juxtaposition teaches that the light of Chanukah can only illuminate the world if we first learn to truly “see” one another. Just as the menorah must be within our line of sight, the people around us - family, friends, and those who are struggling - must remain within our moral line of sight.

Spiritual light and ethical responsibility are intertwined. We cannot bring light to the public square if we are blind to the pain of those closest to us. Chanukah, therefore, calls us to correct the failure of Yosef’s brothers by cultivating empathy, responsibility, and genuine attentiveness to every human being who needs to be seen.

Every marriage deals with this tension. Every family confronts it, as does every community. A moment where we must decide: Do we take the shot for ourselves, or do we look for the open player? Are we focused on our own score, our own streak, our own accomplishments? Or are we ready to see others, help others, elevate others and serve the community and strengthen the whole? Are we only concerned with the Chanukah lights being seen and our own celebrations or are our eyes wide open to see the needs of those around us?

I love the pirsumei nisa aspect of Chanukah, our obligation to publicize the miracle. We share Chanukah candles and gifts with our Jewish neighbors (thanks Barry & Debra Frohlinger!), we host an outdoor menorah lighting, and we blast the holiday’s message of Jewish resilience to inspire the community. Chanukah deserves – and needs – to be seen so that it reminds us to see. We must keep our eyes wide open for what we can do to add light and hope to a world steeped in darkness.

When we choose to seek out – to see – the other, something profound happens: We may lose a personal streak, but we win the game that really matters. Sharing the light of Chanukah is not only about others seeing it but about us seeing others. Greatness is not only measured by how often we score for ourselves, but by how often we see, uplift, and create victories for all. 

Wrestling with Blessing

I admit it. I watched professional wrestling as a kid.

So when Parshat Vayishlach comes around, I can’t help thinking of the first real “main event” in history — and this one wasn’t choreographed.

The Torah gives us the play-by-play:

“And Yaakov was left alone; and a man wrestled with him until the break of dawn.
When he saw that he could not prevail, he struck the hollow of Yaakov’s thigh…
The man said, ‘Let me go, for the day breaks.’
Yaakov said, ‘I will not let you go unless you bless me.’
The opponent said, ‘What is your name?’
He said, ‘Yaakov.’
The man said, ‘Your name shall no longer be Yaakov but Yisrael, for you have struggled with God and with man - and prevailed.’” (Bereishit 32:25–29)

Most commentators debate the identity of the mysterious opponent. I want to look at something else: the nature of the struggle and the surprising truth that the struggle itself becomes the blessing.

Rabbi Joseph Soloveitchik asks a simple question: Why did Yaakov fight at all? Yaakov was no fighter. He was yosheiv ohalim, the quiet student, the man of the tent. Eisav was the hunter, the warrior. What was Yaakov doing in a wrestling match he seemed destined to lose?

The Rav explains that Yaakov was not displaying koach - physical strength. He was displaying gevurah - spiritual heroism. Gevurah begins where logic ends. It’s what happens when a person believes in something so deeply that retreat is no longer an option. A hero in the Torah is not defined by the battles he wins but by the values he refuses to surrender. Heroism is passion, conviction, purpose - even when the odds are against you. That is why Yaakov fights.

Yaakov’s fight foreshadows three dimensions of the Jewish struggle. The Torah uses the word va’yeiaveik. It comes from three related ideas and together they outline the story of Jewish history.

1. Avak - dust. Like dust in the wind, we have been scattered again and again.
2. Avak - to wrestle. We have endured endless physical battles - threats, attacks, persecutions.
3. Va’yechabeik - to embrace. In modern times, our struggle is not only with enemies but with the seductive embrace of assimilation, the pull of a world that wants us to blend in until there is nothing distinct left to protect.

These are the fights of Yaakov. These are the fights of the Jewish people.

Yaakov wrestles the entire night. He emerges limping, injured, forever marked. So, did he win?

The Torah’s answer is yes because victory is not defined by walking away unscathed. Victory is defined by who you become through the struggle. Yaakov receives his new name, Yisrael - the one who struggles and prevails. His wound becomes part of our identity. We remember it every time we avoid the sciatic nerve. It may limit our access to a cut of kosher filet mignon, but the real reminder is not culinary; it’s spiritual.

Our wounds don’t diminish us. Our struggle doesn’t weaken us. Our struggle is part of our blessing.

Last night, I met Effi Eitam, an IDF brigadier general, former leader of the National Religious Party, and like so many others, a man with an October 7th story. When the attacks began, he put on his uniform, got in his car, and drove toward the danger. He found himself face-to-face with a Hamas terrorist and fought. He spoke with pain about two sons wounded in Gaza. He spoke with pride about his grandson in officer training. He spoke with humor about the young soldier — barely older than his grandson — who informed the 72-year-old general that he, the rookie, was now in command. And he spoke with absolute confidence that Am Yisrael will prevail.

Looking at that man, a Yom Kippur War hero who is still fighting, it is impossible not to think of Yaakov: fighting, unbroken, and blessed.

In 1964, Rabbi Soloveitchik wrote his landmark essay Confrontation. He argued that Jewish sacredness requires boundaries, that identity demands clarity, and that not every embrace is holy. Our uniqueness means we cannot dissolve ourselves into the identities or the theologies of others. Struggle does not endanger who we are. Struggle defines who we are.

Today, we face our own confrontation - enemies on the outside, confusion on the inside, a world that too often misunderstands or misrepresents us. Some shrink back. Some despair. And yet so many have stepped into the ring with courage, with conviction, with faith. We may never have the numbers of our enemies, but we have something far stronger: the truth of our story, the strength of our people, and the God Who promised us that struggle leads to blessing.

If we remain engaged in the struggle, we will prevail. Rabbi Jonathan Sacks wrote, “If we know who we are, we need fear neither the hostility of the nations nor their friendship. For we are strong enough to fight for our safety and for our values.” That is the legacy of Yaakov. That is the name Yisrael. That is the message of our generation. We struggle, and we prevail. We are wounded, and we walk forward anyway. We enter the ring again and again because that is who we are.

Randy Fine’s Kippa & the Impact of Being Seen

It’s one of my favorite corny Jewish jokes.

How do we know that Jewish men cover their heads? The Torah says, “Vayeitzei Yaakov – Jacob went out.” Would our holy patriarch Yaakov dare go outside without his head covered?!?

I know, I know…it’s not funny, but I think that Jewish head coverings, impact, and the courage to be seen are important today. Jews must visibly make their presence felt.

Yaakov leaves home with nothing but his identity. No wealth. No family. No protector. Yet everywhere he goes — in Lavan’s home, in the fields, or among strangers, he makes an impact simply by being Yaakov. His presence is a statement. His identity is visible. His character leaves an imprint. Sometimes the most profound influence comes not from what we accomplish, but from who we are — and who we allow the world to see.

Last week at a NORPAC event, I met Congressman Randy Fine of Florida. Randy built a career as a successful entrepreneur and retired at 40. His wife wasn’t pleased with having him home so much and submitted the paperwork for him to run for the Florida House. He won and served in the Florida House and Senate for eight years, before being elected to Congress in April of 2025. His ironclad support for Israel and efforts combatting antisemitism have earned him the nickname “The Hebrew Hammer.”

Randy Fine is also the first Jewish member of Congress to wear his kippa in Congress. He is not fully observant and does not usually wear a kippa. So why does he wear it there?

Before a congressional hearing on campus antisemitism, Fine’s teenage son urged him to wear his kippa so Jewish students afraid to show their identity would know they had an advocate in the room. “The reaction was overwhelming,” Fine recalled. Jewish families across the country reached out in support. That night, his son told him: “You should keep wearing it until every Jewish student in America feels safe.” Fine acknowledged that could take years. “And that’s fine,” he said.

Randy Fine is following in the footsteps of Yaakov. He wears his kippa to send a message of courage, pride, and solidarity: A Jew belongs everywhere — proudly and unapologetically.

Recently, Ben Shapiro called out Tucker Carlson, once a mainstream conservative voice, who has gradually embraced morally dangerous figures and ideas. On a special episode of his podcast, Shapiro played clips of Carlson and white nationalist Nick Fuentes and then called Carlson exactly what he was behaving like: an “intellectual coward” and an “ideological launderer.” As Rabbi Efrem Goldberg wrote, he demanded moral clarity and accountability - a clear line that too many have been afraid to draw. In a time of rampant moral equivocation, “we should be both proud and profoundly grateful that one of the most visible Jews in public life, a man whose yarmulke is as recognizable as his voice, is using his platform to articulate moral truth when so many others remain silent.”

Here in Nassau County, Bruce Blakeman, our member and regular worshipper, stands up for Israel, leads the safest county in America, and the first words of his recent re-election victory speech were, “Thank you, Hashem.”

Bruce Blakeman, Ben Shapiro, and Randy Fine come from different backgrounds, levels of observance, and political worlds, but they share one essential trait: They are Jews who are seen - and they use that visibility to elevate Jewish pride and ethical clarity.

We don’t need to be heroic. We just need to show we’re Jewish.

Decades ago, two Chabad students participated in the summer “Roving Rabbis” program visiting small towns in the south. Unfortunately, in one locale, they didn’t encounter any Jews and reported back to the Lubavitcher Rebbe that “nothing happened.” They felt they had wasted their time. The Rebbe replied that he had received a letter from an elderly woman in that very town. Her grandchildren had laughed when they saw “two strange-looking young men” pass by. From their description, she realized they must be Jewish students. She ran outside to ask them where she could find kosher food and how she could live more Jewishly—but she missed them. So, she wrote to the Rebbe instead. “You see,” the Rebbe wrote them, “You inspired someone just by being there.”

And that is the point: simply being visibly Jewish - our presence, our demeanor, our way of carrying ourselves - can touch hearts in ways we may never know. Every Jew, especially one who is identifiably Jewish, is always making an impression. Without saying a word, we can make a meaningful impact.

We owe a debt of gratitude to those who identifiably stand up publicly and loudly – and should follow their example. In a time when Jews face challenges that may lead us to shrink ourselves, we must choose to be seen. Wear a kippa in more places than usual (if not everywhere), display more Jewish signs and symbols, speak up for Israel and Jewish causes and against those who support our detractors.

Let’s take a page out of the parsha and the headlines. Like Yaakov, Ben Shapiro, Bruce Blakeman, Randy Fine, and so many others, let’s walk visibly, proudly, purposefully, and with the awareness that someone, somewhere, is strengthened simply by seeing a proud Jew.

And so are we.

Please Get Up: Yaakov, ChatGPT & the Importance of Being Polite

“Ha-kol kol Yaakov v’ha-yadayim yedei Eisav – The voice is the voice of Jacob, yet the hands are the hands of Esau.” (Bereishit 27:22)

Yitzchak’s dramatic declaration captures the complexity of the episode in which Yaakov swoops in to receive the blessing instead of his older brother, Eisav.

There are all sorts of questions, interpretations, justifications, and rationalizations. I have always felt that the most straightforward explanation is that if Yitzchak didn’t want Yaakov to receive the blessings, he could have simply changed his mind. It can be compared to a mistaken beracha over food. If I make the wrong blessing over a piece of fruit, I can correct course and say the right one. Nevertheless, exploration and analysis abound.

If we take the text at face value, Yaakov was trying to fool Yitzchak into thinking that he was Eisav. He wore Eisav’s clothes. He hunted and prepared food like Eisav. And he responded to Yitzchak’s questions as if he was Eisav. When all is said and done, Yitzchak still has his doubts due to the voice. This begs the question: Why didn’t Yaakov try to sound more like Eisav? Would it have been so hard?

The answer can be found in a very clear distinction between how Yaakov speaks and Eisav speaks.

When Yaakov enters Yitzchak’s tent disguised as Esav, he graciously invites his father to eat:
“Kum na, sheva ve’achla mi’tzaydi - Please get up, sit and eat of my food…” (Bereishit 27:19)

Later, when the real Esav arrives, the contrast between invitations is stark: 
“Yakum avi ve’yochal mi’tzayd b’no - Get up, my father, and eat the food” (27:31)

Yaakov says “na – please”. Esav does not.

That was the “tell,” the clue, to Yitzchak that something wasn’t right. If Yaakov wanted to deceive his father, logic suggests he should have copied Esav precisely - tone, mannerisms, and yes, even speaking style. Yet Chazal note that Yaakov simply could not bring himself to speak brusquely. Despite the pressure, despite the mission, despite his mother’s urging, he could not omit the word “please.”

It is not merely a stylistic difference; it is a window into their souls – and ourselves.

The Midrash highlights that the word “na” is one of the Torah’s markers of derech eretz — polite, gentle, respectful behavior. Yaakov’s character was so deeply embedded with menschlichkeit that even deception could not override it. Esav, for all his genuine love for his father, did not have the same instinct. He honored Yitzchak but politeness was not part of his inner language.

This small linguistic difference helped Yitzchak sense something was off. The voice may have been disguised, the clothing altered, but the word “please” gave Yaakov away. Because how we speak is who we are. Language reveals identity; polite language reveals values.

This ancient contrast has found surprising new relevance in a modern debate: Should people say “please” and “thank you” to Artificial Intelligence (AI) systems like ChatGPT?

A recent survey found that around 70% of AI users are polite to AI systems. The majority do it simply because "it's the right thing to do." They insist that politeness is intrinsic to good communication and expresses a form of human dignity. Others argue that polite phrasing can sometimes slow down responses or cause AI systems to expend more computational resources and is a waste of energy. They claim we should be direct, efficient, and economical.

While Judaism’s view on being polite with AI has yet to develop, we know that derech eretz and menschlichkeit are part of our religious DNA.

Israelis may be known for their gruff disposition, but Jewish law presents several examples of obligatory polite behavior. It is forbidden to ignore the greetings of another and not respond to another person telling you hello, good morning, or “Shalom Aleichem.” One who ignores another person’s greetings is called a “gazlan,” and it is viewed as if one stole. Not responding to a greeting can cause enmity to spread between the two parties. It is for this reason that the Sages require one to proactively greet others, to increase love and peace and avoid potential machloket.

Please is more than a nice word. Yaakov didn’t say “please” because Yitzchak required it. Yaakov said “please” because that’s who Yaakov was. Politeness is not about the recipient. It is about the speaker. We say “please,” “thank you,” and “excuse me” not to manipulate responses, not to optimize processing time, not to conserve computational power but because polite speech shapes our character. It refines our souls. It reminds us that words matter.

ChatGPT does not need politeness, but we do. If we train ourselves to be curt and transactional with machines, we risk importing that tone into our interactions with humans. Speech patterns become habits; habits become character. And character - as the Torah repeatedly emphasizes - is destiny.

Yaakov teaches that derech eretz does not get suspended for convenience. Even at a moment of crisis, his speech remained infused with grace. That’s who he was. That’s who we need to try to be. Polite speech is not a luxury or an extra flourish; it is the foundation of being a mensch. The louder, more automated, and the more confrontational our world becomes, the more vital it is that we preserve that foundation.

“Nafshi yatza b’dabro – A person’s soul is revealed when they speak.” (Shir HaShirim 5:6) Say “please.” Say “thank you.” Say “good morning.”  Not because someone – or something – else needs it. But because we do.