How Moshe Rabbeinu Teaches Us to Pray

Every Jew prays. Three times a day we stand before the Ribono Shel Olam, open our siddurim, and pour out our hearts. Yet one fundamental question deserves our attention: What is the proper mindset when we stand before Hashem? Parshat Va'etchanan answers that question—not through abstract theory, but through the personal example of Moshe Rabbeinu. At the end of his life, the Torah allows us to witness one of the most moving prayers ever offered. Through Moshe's tefillah, we discover what authentic prayer is meant to be. Our member Rabbi Paul Bloom explains.

The Prayer That Was Never Granted

Moshe Rabbeinu was 120 years old. He had led the Jewish people out of Egypt, stood at Har Sinai, taught the Torah, and guided the nation through forty years in the wilderness. Yet there remained one dream he longed to fulfill. He desperately wanted to enter Eretz Yisrael.

Again and again he pleaded with Hashem to allow him to cross the Jordan and experience the holiness of the Promised Land. The Midrash teaches that he prayed 515 times, exhausting every avenue of supplication. Yet the answer remained the same: No.

At first glance, this seems puzzling. If Moshe's request would ultimately be denied, why does the Torah devote so much attention to his prayer? The answer is profound. The Torah is teaching us that the value of prayer is not measured solely by whether the answer is yes.

Sometimes "No" Is Also an Answer

Hashem tells Moshe that he may not enter the Land "because of you." The Netziv explains that this does not mean Moshe was being punished. Rather, it means that the Divine plan required a different leader for the next chapter of Jewish history. Moshe was the perfect leader to bring the Jewish people out of Egypt and receive the Torah. Yehoshua was the leader needed to bring them into the Land of Israel.

The refusal had nothing to do with Moshe's worthiness. It reflected a larger Divine plan that extended beyond one individual's deepest desire. How often do we experience the same struggle? We pray sincerely for healing, livelihood, success, or guidance, yet the answer is not what we hoped for. Parshat Va'etchanan reminds us that an unanswered prayer is not necessarily a rejected prayer. Sometimes Hashem sees a larger picture that we cannot yet understand.

Prayer Is Never Based on Merit

The Torah's choice of language is equally instructive. Moshe begins his prayer with the word "Va'etchanan"—"I pleaded." Rashi explains that this word teaches a fundamental principle of Jewish prayer. One never approaches Hashem saying, "Please answer me because I deserve it."

If anyone could have claimed merit, it was Moshe Rabbeinu. After all, he split the Sea, ascended Har Sinai, taught the Torah, and devoted his entire life to serving the Jewish people. Yet even Moshe asks only for a gift of Divine kindness. This is precisely how our daily prayers begin. We appeal not to our accomplishments, but to Hashem's boundless mercy. Everything we receive is ultimately an expression of His kindness rather than something we have earned.

The Power of Holy Longing

One detail in the narrative seems almost painful. Hashem tells Moshe:

"Go up to the mountaintop and look at the Land."

Imagine telling someone who has dreamed all his life of entering a beautiful home that he may look—but never enter. Why would Hashem do this? Because the longing itself possessed enormous spiritual value.

Moshe's overwhelming desire to enter Eretz Yisrael was itself an expression of love for the Land and for the mitzvot that can only be fulfilled there. The Gemara explains that Moshe did not seek the Land for personal comfort or prestige. He yearned to fulfill the unique mitzvot dependent upon the Land of Israel—mitzvot connected to its agriculture, its holiness, and the Beit HaMikdash. Even though he could not realize that dream physically, the depth of his yearning became an eternal lesson for the Jewish people. Sometimes, spiritual greatness is found not only in achieving a goal but in yearning for it with all one's heart.

The Meaning of 515

Chazal note that the numerical value (gematria) of Va'etchanan is 515, corresponding to the number of prayers Moshe offered. Interestingly, the same numerical value equals the word "tefillah" (prayer). The message is striking. Moshe's prayers were not failures because they did not produce the desired outcome. They became the very definition of prayer itself. True tefillah is not measured only by results. It is measured by sincerity, humility, faith, and the willingness to place our deepest desires before Hashem while accepting His ultimate wisdom.

The Second Half of Prayer

Parshat Va'etchanan teaches another essential dimension of Jewish worship. Not every part of our daily service is a request. Immediately after Moshe's prayers, the Torah presents the Shema. Unlike the Amidah, the Shema contains no petitions. We ask for nothing.Instead, we fulfill the mitzvah of Kabbalat Ol Malchut Shamayim—accepting the Kingship of Heaven. It is, in effect, Judaism's daily pledge of allegiance.Just as citizens pledge loyalty to their nation, every Jew begins and ends the day by declaring unwavering loyalty to Hashem. When we proclaim:

"Shema Yisrael, Hashem Elokeinu, Hashem Echad,"

we reaffirm our identity, our covenant, and our mission.

A Conversation Across Generations

The Gemara adds another beautiful insight. When Yaakov Avinu lay on his deathbed, he wondered whether all twelve of his children would remain faithful to the covenant. His sons answered him with the words "Shema Yisrael." In that context, "Yisrael" refers to their father, Yaakov. Every time we recite the Shema, we are joining that timeless conversation. We declare to our ancestors that their faith lives on within us. We stand as another link in the unbroken chain of Jewish history, pledging our loyalty to Hashem and to Klal Yisrael.

A Message for Our Generation

The transcript concludes with a moving contemporary reflection. In the aftermath of October 7, many Israelis who previously viewed Jewish identity primarily through cultural or political lenses began to rediscover the spiritual foundations of the Jewish people. One secular Israeli intellectual expressed it poignantly:

"The only answer to 'Allahu Akbar' is 'Shema Yisrael.'"

Regardless of one's perspective, the point is deeply meaningful. In moments of uncertainty and crisis, Jews instinctively return to the words that have sustained us for thousands of years. The Shema is more than a prayer. It is our declaration of faith. It is our statement of identity. It is our pledge of allegiance to the Ribono Shel Olam.

Two Pillars of Jewish Prayer

Parshat Va'etchanan teaches that authentic Jewish prayer rests upon two inseparable foundations. First, like Moshe Rabbeinu, we bring our hopes, fears, and needs before Hashem with humility, recognizing that every blessing is a gift of Divine kindness. Second, before asking for anything, we reaffirm our covenant through the Shema, declaring that we belong to Hashem, to His Torah, and to Klal Yisrael.

These two elements—petition and commitment—form the heartbeat of Jewish prayer.May we learn from Moshe Rabbeinu to pray with humility, to accept Hashem's wisdom even when His answers differ from our requests, and to renew each day our eternal declaration:

"Shema Yisrael, Hashem Elokeinu, Hashem Echad."

Never to Pray Alone: Va'etchanan 5786

This piece by Rabbi Kenigsberg was first published in the Hanassi Highlights, Wednesday 22 Jiuly. You can read it in Hebrew, thanks to ChatGPT, here.

The opening of Parshat Va'etchanan is one of the Torah’s most poignant moments. After forty years of leading the Jewish people through the wilderness, Moshe Rabbeinu asks for just one thing: the privilege of entering Eretz Yisrael.

Chazal famously note that the numerical value of the word Va'etchanan is 515, teaching that Moshe prayed no fewer than 515 times to be allowed into the Land. Few images capture the power of perseverance in prayer more vividly than this. Moshe refuses to give up, pouring out his heart again and again, even as the answer seems increasingly out of reach.

Yet only a few verses later we encounter a puzzling statement. Addressing the people, Moshe says: "Hashem became angry with me because of you, and He did not listen to me."

The words seem difficult. The Torah itself makes clear that Moshe Rabbeinu's inability to enter the Land was connected to the events at Mei Merivah. How, then, can he say that Hashem refused his prayer "because of you"?

Some explain that Moshe is referring not to punishment but to leadership. He was the leader uniquely suited to guiding Israel through the wilderness; the next generation required a different kind of leader. "Because of you" means that, for the sake of the people, history demanded that Yehoshua lead them into the Land.

Rav Soloveitchik, however, hears something even deeper in these verses.

Notice the opening word: Va'etchanan - I pleaded. It is singular. It is the prayer of one person standing alone.

Throughout his life, Moshe Rabbeinu never prayed only for himself. After the sin of the Golden Calf, after the episode of the spies, and on countless other occasions, he stood before Hashem on behalf of the Jewish people. Their suffering became his suffering; their fate became his concern.

This time was different.

According to the Midrash, had the people joined Moshe in prayer, the decree might have been overturned. The sin at Mei Merivah was indeed his own. But the loneliness of Va'etchanan - the fact that he carried this burden without the prayers of those for whom he had prayed so often --- belonged to the people.

Perhaps this is one of the enduring lessons of communal life.

A shul is not merely a place where people happen to pray in the same room. It is a place where a community gathers to carry one another's hopes, worries and burdens before Hashem. We rejoice together, we mourn together, and we pray not only for ourselves but for all those around us too.

Shabbat Nachamu, the first Shabbat after Tisha b'Av, marks the beginning of comfort and rebuilding. Perhaps that rebuilding begins not only with grand visions of redemption but with simple acts of responsibility for one another. The journey from the loneliness of Churban to the consolation of Nechamah is paved by communities that notice one another, care for one another, and pray for one another.

May we take to heart the lesson of Va'etchanan: that no Jew should ever have to stand before Hashem alone. May our tefillot, offered together and for one another, bring comfort, healing and redemption to all of Am Yisrael.

Shabbat Shalom!

The nuance of desire: Va'Etchanan 5785

The Torah, as we all well know, is multilayered. The rabbis have taught us that there are 70 facets to every piece of the written Torah. We are also aware that it is impossible to adequately convey every nuance and possible meaning that lies embedded in the Torah. Each word demands elucidation, commentary and explanation before we can gain any proper understanding of its message. The entire book of Devarim is itself an elucidation and explanation of the first four books of Moshe. This is why Devarim employs different words to describe those events and commandments that were mentioned earlier.

A prime example is the repetition in this week’s parsha of the Ten Commandments revealed to Israel at Sinai: the text here differs slightly from the wording recorded in the book of Shemot. The Talmud, in its rendition of the Oral Law, states that these variants—such as the use of the word shamor for the observance of Shabbat instead of zachor—indicate that God uttered both words simultaneously, a feat that is beyond human comprehension and ability. The Talmud means to show us that every possible interpretation and layer of meaning in the Torah was delivered in one go at Sinai. Only the Oral Law and the work of Torah commentators through the ages has revealed these original strata of meaning for our study and practice.

In the last of the Ten Commandments, the Torah here in Parashat Va'Etchanan uses the word titaveh whereas in Parashat Yitro it uses the word tachmod. Both words mean “desire”, but they are differently nuanced.  One carries overtones of an impulsive, spur of the moment desire that arises out of seemingly random circumstance – an advertisement in the media or a chance meeting or sighting. Such a desire is not planned, but stems from our inherent human weakness in wanting to possess what we do not yet have. The other desire is long planned and may have been part of our lives for years or even decades. It borders on being an obsession or an addiction within our makeup. Both types of desire can destroy a person and the Torah cautions us against these symptoms of self-destructive behavior.

The Talmud tells us that the eyes see and the heart then desires. Guarding one’s eyes guards one’s heart as well. This example of the Torah’s self-elucidation makes each lesson clear to all and challenges us to apply it wisely in our own lives. 

Shabbat shalom, Rabbi Berel Wein

For "Comfort and Contentment", Rabbi Wein's devar Torah on this parashah last year, click here.

What are we doing when we say Shema?

Sometimes our own familiarity with the things we daily say, see and hear can cause us to stop thinking about their meaning and significance. We say Shema each day, but must never take it for granted. Our member Paul Bloom looks further into this mitzvah and points out things we may easily miss.

One of the most famous sentences in the entire Torah is:

 שְׁמַע יִשְׂרָאֵל ה׳ אֱלֹקֵינוּ ה׳ אֶחָד

This pasuk is found in our parashah. We say it every day. But what does it really mean?

Rabbi Alan Kimche explains something powerful: even though Shema appears in the siddur, it’s not actually a prayer — at least not in the way we usually think of prayer. Normally, in tefillah, we ask Hashem for things: health, peace, livelihood, wisdom, redemption. But Shema is different. It’s not a request — it’s a declaration. A pledge of allegiance.

Just like soldiers pledge loyalty to their country, when we say the Shema, we are pledging our loyalty to Hashem, to the Jewish people, and to our mission in this world. And those first two words — “Shema Yisrael” — aren’t just a poetic beginning. They’re a command: Listen. Pay attention. Tune in.

Why “listen”? Why not “see”? Rav Yitzchak Hutner points out that seeing can mislead us — it’s easy to be fooled by appearances. Just think back to the very first sin in the Torah: Chava saw the fruit and it looked good — and we all know where that led. But true understanding, true depth, comes from listening. Hearing the voice of Hashem, hearing the wisdom of Torah, listening to the truth that often can’t be seen with the eye, only felt in the heart. That’s why we cover our eyes when we say Shema — because the truths we’re affirming aren’t visible in the world around us. The world today looks divided, broken, chaotic. But we say “Hashem Echad” — we declare that beneath it all, there is unity. There is a Divine plan.

Another beautiful idea comes from the Maharal of Prague. He explains that when we say “Shema Yisrael,” we’re not talking to Hashem — we’re talking to each other. To all of Am Yisrael. This isn’t just a personal statement. It’s a national mission. I don’t say Hashem is my God — I say He’s our God. We’re in this together.

There’s a third layer — from the Sfas Emes. He reminds us that we actually heard the first two commandments directly from Hashem at Har Sinai — not through Moshe, but with our own ears. That voice of Hashem still echoes in the world, even if we can’t hear it in the usual sense. When we say the Shema, we’re reconnecting to that eternal voice.

And finally, the Gemara tells us something beautiful: the very first people who ever said “Shema Yisrael” were the sons of Ya’akov Avinu. When Ya’akov was on his deathbed, he asked his sons if they shared his faith — and they replied: “Shema Yisrael” — Listen, our father Yisrael, Hashem is our God, Hashem is One. In that moment they were saying, “We are with you. We carry your faith forward.” And so when we say Shema today, we’re also speaking to our ancestors — saying to them: “We are still here. We believe. We continue your path.”

We are part of that eternal chain. When we say “Shema Yisrael”, and we connect to Ya’akov, to Har Sinai, to thousands of years of Jews who came before you — and, IY”H, to generations who will come after us.

Comfort and contentment: Va'Etchanan 5784

This week, with Shabbat Nachamu we begin a cycle of comfort and consolation following the weeks of sadness and mourning over the past tragedies of the Jewish people. The next seven weeks of comfort and healing will lead us into the new year that awaits us. But we begin, in this week’s parsha, with a synopsis and summary of all Judaism: the Ten Commandments, the Shema and the explanation of the Exodus from Egypt that we give to the wise son at the Pesach seder. 

Broadly speaking, this parsha encapsulates the entire structure of Torah and Jewish life. Since the reading of Va’etchanan invariably falls on Shabbat Nachamu, we can see how the Torah is teaching us that comfort and consolation are spiritual values and attainments: these things do not necessarily depend on material wealth or worldly success. Our society, so rich in material goods and advanced technology, suffers greatly from all sorts of mental and social dysfunction. Depression is the “black dog” (as Churchill described his recurring bouts of this condition) that affects over a third of the citizens of the Western world at some time in their lives. True comfort and serenity are difficult for human beings to achieve and even harder to sustain. 

This week’s Torah reading offers us a formula to achieve the elusive goal of contentment. And it lies within the parameters of those three principles of Jewish faith which it outlines. 

The Ten Commandments establish a structure of belief and morality to which every individual can ascribe and aspire, no matter how decadent the society in which we are enmeshed. The moral strictures that protect life, person and property are the basic rules of Jewish life and faith. Given the dysfunction between parents and children, a commercial world that never sleeps, acceptance of robbery and corruption as social norms, daily murders and a sexually dissolute society, how can one avoid being depressed?  Though civilization teeters on the brink of self-destruction, the Ten Commandments point the way out of the social morass into which we are sinking. The Shema is the vehicle of connection of our soul with the Creator who fashioned us and gave us life. Belief in the one and universal God, the omniscient and omnipotent ruler, is the greatest gift of the Jews to the human race. This belief gives us discipline and security, purity and nobility, the whiff of immortality and a sense of purpose in knowing that life is never in vain. 

Finally, understanding the uniqueness of Israel in God’s scheme of things as represented in the story of the Exodus from Egypt, gives structure and perspective to our national and personal lives. But it takes wisdom and knowledge—a wise son—to appreciate and treasure this memory of the distant past. This memory alone can also give us a sense of comfort and well-being and contribute towards the consolation and contentment we so ardently seek. 

Shabbat shalom, Rabbi Berel Wein