As we explained in the introduction, Tehillim gives expression to every state of the human soul. It is a structure that shows us from the very start , how a person should be aligned spiritually.
Tehillim begins:
“אַשְׁרֵי־הָאִישׁ אֲשֶׁר לֹא הָלַךְ בַּעֲצַת רְשָׁעִים וּבְדֶרֶךְ חַטָּאִים לֹא עָמָד וּבְמוֹשַׁב לֵצִים לֹא יָשָׁב”
The Targum translates Ashrei as טוביה דגבר, “the good of man.” A person is considered good when he is spiritually aligned.
Rav Aharon Kotler1 explains that the continuation of the pasuk teaches that even when a person is spiritually aligned, he must remain cognizant of his surroundings. The moment that alignment weakens, he begins to slide down a slippery slope.
Rav Elchanan Wasserman2 adds that a person cannot assume that nothing will happen to him. One must always be careful to maintain that alignment.
It is interesting that Dovid HaMelech chose to begin Tehillim in a negative tense. Instead of describing that one is fortunate to walk with tzaddikim, stand with the upright, and sit with the wise, he begins with what must be avoided.
My father, Rabbi Yaacov Haber, explains that this is because a person begins life fundamentally good. We were created with a neshamah. The danger is not that I lack goodness, but that I allow myself to become bent away from my intrinsic goodness.
There is a dual progression in the pasuk: between rasha, chotei, and leitz, and between halichah (going), amidah (standing), and yeshivah (sitting). Man is a social being.
Let’s explain.
We have the rasha, chotei, and leitz—and we have what they are doing. These are not redundant.
A rasha is someone who does wrong deliberately. This is evil with intention.
A chotei, in this context, is someone drawn by impulse, carelessness, or ignorance. The wrongdoing is real, but it is not rooted in deliberate rebellion in the same way.
A leitz is a different kind of problem altogether. A leitz does not necessarily commit a dramatic act of evil. A leitz takes what is serious and empties it of seriousness. He trivializes what should matter.
A moshav leitzim is dangerous because it is an environment. It is a place where life itself is made weightless. Time is the most serious thing I possess. If I sit in a culture of empty amusement, endless cooling and irony, I take the most precious thing I have and convert it into nothing. That is ruinous and the ultimate misalignment.
The next set of three is the verbs: walking, standing, sitting. Alongside them are three structures:
Eitza — the counsel of the resha’im, deliberate, thought-out direction
Derech — the path of chata’im, habit and impulse
Moshav — the seat of mockery, leitzanus, which does not exist in motion, but is atmospheric.
When a person is working on self-development, before starting with anything positive, he must first recognize where he is standing. Only once a person becomes aware of the surrounding negative influences (ra) can he begin aseh tov and remain aligned.
Ashrei refers to the solidity of the person. A person who is me’ushar is a person who is authentic, and of substance.
The word עמד corresponds to asiyah, machshavah, and dibbur.
The progression of הלך → עמד → ישב reflects increasing levels of involvement. A person must not participate in the path of chotim in any form—not in thought, speech, nor action.
The Alshich explains that there are two types of happiness: one that comes from סור מרע, turning away from wrongdoing, and a higher level that comes from עשה טוב, actively doing good.
However, not everyone who avoids wrongdoing is called ashrei. Only one who fully separates himself from all three dimensions of sin, and then redirects himself properly through Torah, reaches that level.
These three dimensions are:
Thought without action which is associated with the soul
Action without thought which is associated with the physical
Speech which stands between the two
One who refines and guards all three is considered complete and is therefore worthy of being called ashrei.
The Ben Yehoyada3 explains that this entire pasuk is referring to Avraham Avinu4. The perek begins with ashrei ha-ish instead of ashrei ish—the extra hei indicates a specific individual, namely Avraham, whose name had a hei added to it.
The Maharsha5 explains how each part of the pasuk reflects Avraham’s life.
“לא הלך בעצת רשעים” refers to the Dor HaPelagah. They promoted unity and brotherhood, but used it for negative purposes. Avraham rejected that entirely and instead embodied unity, love, and connection in a positive way.
“ובדרך חטאים לא עמד” refers to Sedom. Their defining trait was the rejection of chesed. Avraham stood in direct opposition to them, going to the other extreme of actively pursuing hachnasas orchim and constant kindness.
“ובמושב לצים לא ישב” refers to the Plishtim, who degraded Shimshon and were steeped in immorality. (As Chazal describes, the Plishtim brought their wives to Shimshon in prison in an attempt to conceive from him.) Avraham was so removed from that world that he did not even recognize Sarah’s beauty until they arrived in Mitzrayim6.
According to this, the pasuk is describing a model, rather than an abstract person. Avraham HaIvri is the prototype of what it means to be ashrei ha-ish.
The Chomas Enech (Chida) adds a different dimension. Even when a person begins to slip unintentionally, the response has to be immediate. He should react with humility and tefillah, asking Hashem for forgiveness. That immediate response prevents a small mistake from developing further.
He points out that this is hinted to in the roshei teivos of ashrei ha-ish:
אם שגג רחמים יבקש ה׳ אלהים יסלח שגגתו—if a person sins accidentally, he should immediately seek rachamim so that it does not become something more serious.
The Meiri approaches ashrei from a different angle. He notes that the word is always in the plural form. Ashrei is not describing a single success or moment of happiness, but a collection of successes. A person is called ashrei because his overall direction is one of consistency and alignment.
He then takes the pasuk further. It is not simply praising someone for avoiding obvious evil. It would not make sense to say “fortunate is the one who is not a rasha”. Rather, the praise is for someone who separates himself from what most people are naturally drawn toward and chooses to direct his life toward Torah and avodas Hashem.
Like the Ben Yehoyada, this again points toward Avraham HaIvri as someone who stood apart.
The Meiri then redefines the three categories in a very practical way:
Resha’im — those chasing money, power, and gain. Those living with a constant drive for more.
Chata’im — those drawn after physical pleasure beyond what is necessary
Leitzim — those who waste their time, sitting in empty conversation and distraction
The chiddush of the Meiri is that the pasuk is describing the real ways people drift: chasing success, chasing pleasure, or simply wasting time. That is bringing it beyond just a warning against extreme evil.
Ashrei ha-ish is someone who steps away from all of that because he wants to live with focus and purpose.
Rav Moshe Dovid Vali (Ramdu) explains7 that the word ashrei parallels the level of binah, which Dovid HaMelech attained. After Dovid came Shlomo, who reached the level of chochmah and expressed that through Shir HaShirim.
The Ramdu explains further8 that just as there is a structure of sefiros belonging to the side of kedushah, there is an opposing, parallel structure belonging to the Sitra Achra, on the side of tumah.
According to this, the pasuk is not only describing a general individual, it is Dovid speaking about himself. He is ashrei because he was not drawn after the Sitra Achra, which constantly attempts to pull a person away from alignment with the Creator.
Malchus, on its own, is the highest level a worldly king can reach. But Dovid understood that malchus must be connected upward—to the structure of the sefiros above it. That is what made his kingship different.
Even after his sin with Batsheva, he did not allow himself to spiral downward. He did teshuvah and realigned.
He explains9 that because Dovid was able to align himself properly and remain focused, he merited to be part of the Merkavah together with the Avos.
He continues10 that this is why Tehillim begins with this perek. Because a person’s tikkun—and his corruption—both come from his associations. There are “friends within” and “friends without,” visible companions and invisible ones.
The inner companions are the forces of the yetzer hara.
The outer companions are the people a person associates with.
The visible companions are those he sees and hears.
The invisible ones are the forces of the Sitra Achra, which are constantly present, trying to cause him to stumble.
Ashrei ha-ish is the one who does not listen to their counsel and does not follow their pull.
He is crowned with a crown of holiness upon his head and will merit the life of the World to Come, where true and lasting happiness exists. This is unlike life in this world, which ends in dust, decay, and worms.
This also explains the progression of the pasuk. A person does not begin by fully joining. First he walks. Then he stands. Then he sits. Once he begins moving in that direction, it develops.
As Chazal say, “If the spirit of the ruler rises against you, do not leave your place.” If a person begins to walk, he will eventually stand. If he stands, he will eventually sit. The pull strengthens until it becomes settled.
Now how does one stay aligned? Dovid HaMelech tells us in the next pasuk:
“כי אם בתורת ה׳ חפצו ובתורתו יהגה יומם ולילה”
“Rather, his desire is in the Torah of Hashem, and in his Torah he engages day and night”11.
Rav Moshe Dovid Vali12 explains that through Torah, the yetzer tov is strengthened while the yetzer hara is subdued. Torah is not just information—it is what maintains alignment.
Rashi13 unlocks the entire perek. At first it is called Toras Hashem, and after a person labors in it, it is called Toraso—his Torah.
This transition is baffling. It sounds like a downgrade, from Hashem’s Torah to one’s own Torah.
Because of this, the Radak and Ibn Ezra explain that both phrases are referring to Hashem’s Torah. But Rashi clearly means something deeper.
The Maharsha14 explains that the difference is between encountering Torah and being transformed by Torah. At first, the Torah is outside of me. I learn it, I engage with it, but it has not yet entered me. If I work on it properly, if I work on it until it penetrates, it becomes internal. It shapes how I think and how I see the world. At that point it is called Toraso, not because I own it, but because it has become part of who I am.
The Be’er Avraham focuses on the word cheftzo. Everything begins with desire. A person must first want Torah. Even before full actualizing it, that desire already has value. From there, through consistency, yomam valayla, it becomes internalized and part of him.
Like a tree planted by water that gives fruit in its proper time, the result may not be immediate, but it is meaningful and lasting. In contrast, the success of the wicked is superficial—lacking substance, like chaff blown away by the wind.
Rav Zundel Kreuser15 explains that this refers to one who develops chiddushim in Torah and is willing to invest in it fully, even at the expense of his social life. Torah becomes central.
Rav Moshe Dovid Vali16 explains that Toras Hashem refers to the Written Torah, while Toraso refers to the Oral Torah. Alternatively, he explains that the Written Torah corresponds to learning by day, and the Oral Torah to learning at night. The two together form a complete engagement with Torah.
The Alshich explains that Torah itself has two dimensions: sod and peshat.
Sod is the deeper dimension that relates to Hashem, while peshat is the revealed dimension that relates to man.
While not everyone merits reaching the level of Sod, it is still essential to desire it. Toras Hashem refers to the deeper dimension, while Toraso refers to the revealed Torah that a person learns, internalizes, and makes his own.
Reb Nosson17 explains this on a deeper level.
Chazal say that Hashem “engages in Torah.” This does not mean learning in the usual sense. Hashem does not need to learn. Rather, Hashem draws down the light of Torah and shapes it—לצייר—into a form of brachah before it enters the world. Before that process, the light is hidden and undefined.
The same thing happens when a person learns Torah. Before Torah is clarified, its light is present but not yet formed. As a person learns, struggles, and clarifies, he is shaping that light. According to how he approaches it, that is how the light takes form for him.
So too, Hashem כביכול “learns Torah” to shape the upper light—which is completely hidden—into something that can come down as blessing. The tzaddik shapes that light into truth and clarity. The rasha can take that same light and distort it, turning it into confusion or even a stumbling block.
Therefore, Toras Hashem means the Torah as it is given in its true form, and Toraso means how that Torah is now being shaped through the person.
Torah is something you shape while you learn it. How it is shaped depends on the person—his mindset, his honesty, and his inner state.
The focus of this perek is that David is describing a person who becomes substantial. The distinction between a tzaddik and a rasha is ontological more than behavioral. It is about what kind of person I have become.
That is why the next pasuk shifts to the metaphor of the tree:
“והיה כעץ שתול על פלגי מים אשר פריו יתן בעתו ועלהו לא יבול וכל אשר יעשה יצליח”
“He shall be like a tree planted by streams of water, which gives its fruit in its season, its leaf does not wither, and all that he does prospers”18.
The word “שתול” is important. It means transplanted. Left to itself, a tree may survive or fail depending on rainfall, terrain, and circumstance. Two trees can stand a few feet apart with one flourishing and the other struggling, simply because one receives water and the other does not.
But a tree planted by flowing water is no longer left to chance. It is rooted in a constant source, as its irrigated steadily and is stable.
That is Dovid HaMelech’s image of the person who has made Torah his own. He is rooted and therefore consistently successful. He gives fruit in its season because the source beneath him is dependable. His leaves do not wither because even the outer expressions of his life are sustained by something real.
“וכל אשר יעשה יצליח” means that what comes from him is lasting and alive.
Rav Moshe Dovid Vali19 explains that “בעתו” teaches that a person should not become discouraged if he does not see immediate results. Even if he learns and forgets, everything has its proper time. If the desire is real and he does not give up, the fruit will come.
The Alshich explains that the tzaddik is compared to a tree planted in a place of purity, even if its branches extend into areas of impurity. When a person roots his neshamah in Torah (through constant learning) it is like watering a tree. That watering produces fruit. The Chida20 adds that this requires humility. The final letters of “והיה כעץ שתול” equal ענו (humble), with the kolel (the word itself). Without humility, the tree cannot properly receive.
The fruit are his chiddushim, the insights that come specifically from his connection to Torah. The Arizal21 explains that a person should learn the part of Torah he is drawn to. That is not random, it reflects what he came to fix in this world. One person is drawn to Hilchos Shabbos, another to Bava Kama, yet another to deeper sefarim. That piece that he learns is his chelek.
The Chida brings from the Maggid Meisharim that the Maggid told the Beis Yosef that one of his explanations in the Rambam was exactly correct, but the other should not be discarded. Even if it is not the Rambam’s intent, it is still a chiddush, and HaKadosh Baruch Hu takes pleasure in it. Every bit of intellectual effort in Torah has lasting value.
The Alshich adds that if a person is meant to reveal a certain chiddush and becomes lax in his learning, it is like withholding water from the tree. That fruit will not emerge, and he may have to return in a gilgul to complete it.
Rav Moshe Dovid Vali22 similarly explains that a person learns best in the area his heart is drawn to. That is where he will succeed, because that is tied to his tikkun.
Every person in Klal Yisrael has a chelek in Torah. In the part that truly connects to him, he will find chiddushim. Torah has an infinite depth, and each person has access to his portion within it.
And what’s the effect?
“אשר פריו יתן בעתו”—the fruit are the Torah and mitzvos a person produces in their proper time.
“ועלהו לא יבול”—the leaves do not wither.
Aside from producing fruit, a healthy tree can be damaged from the outside. That brings us to a different task, to protect the tree.
Reb Nosson explains23 that the essence of the melachos of Shabbos is the concept of carrying from one domain to another. This is why there is a tikkun of an eruv.
Just as a person must be careful what enters and exits his own domain, he must also be careful not to enter someone else’s domain.
A person should not look at others and imitate them, even if they appear to be doing the right things. He must remain aligned with his own soul, rather than trying to live someone else’s path. The real danger here is not only falling in with bad influences, but comparison itself.
A person can be inspired by others, but if he begins to lose his own direction by trying to become someone else, he is no longer rooted. He has stepped out of his own domain and becomes misaligned.
The Alshich concludes that the success of the tzaddik is lasting, even in matters of parnassah. It is not temporary and fleeting like the seeming success of the rasha.
As Rav Moshe Dovid Vali24 explains “ועלהו לא יבול” refers to the external aspects of life. Even those are not diminished by Torah. On the contrary, when Torah is primary, everything else is sustained properly.
“וכל אשר יעשה יצליח”—the word “יעשה” has the gematria of שכינה, hinting that the Shechinah rests upon such a person and brings success to his actions. The leaves—worldly matters—are secondary, but they are sustained because the root is strong.
The Meiri explains that just as a tree by water never loses its moisture, so too a person’s Torah will not be forgotten. And just as the tree gives fruit at the proper time, so too he will eventually give over his Torah to others. In other words, he will share his wisdom with others after perfecting himself. Thus the fruit is teaching the Torah to others.
He explains further that “ועלהו לא יבול” does not mean the leaves do not fall, but that they do not decay. A person is able to balance his spiritual and physical needs. Alternatively, the leaves represent middos tovos which protect and enhance the Torah itself.
Through this, “וכל אשר יעשה יצליח”—his Torah, his actions, and even those who come after him will endure. Torah penetrates a person. It changes him completely. Even his ordinary speech carries a different quality.
This is the depth of what Dovid is describing. A person who becomes rooted in Torah becomes stable, real, and enduring. He becomes a partner—a shutaf—with Hashem. It becomes Toraso. And it affects every part of who he is.
Now in pasuk daled, Dovid returns to contrast:
“לא כן הרשעים כי אם כמוץ אשר תדפנו רוח”
“Not so the wicked; rather they are like chaff that the wind drives away”25.
The rasha is not like the tree. He is like chaff—light, unstable, and without permanence.
Chaff can look like part of the grain, but it is only the outer husk. Its role is temporary. Once the grain is separated, the wind carries it away. It has no enduring substance. It is appearance without core.
That is how wickedness often presents itself. It can look successful, even impressive—wealth, power, influence, image. But if there is no inner substance, then it is all chaff. The moment circumstances change, it disappears. We see often how people gather around someone because of position or success, and the moment that is gone, everything falls apart. That is chaff.
Torah is not like that. A person rooted in Torah remains who he is regardless of circumstance, because his source is internal and continuous.
Rav Moshe Dovid Vali26 explains that wheat—חטה—has the numerical value of 22, corresponding to the twenty-two letters of the Torah. Just as wheat nourishes the body, the letters of Torah nourish the soul. The chaff, by contrast, has no substance and is scattered by the wind.
Dovid now closes the contrast:
“על כן לא יקמו רשעים במשפט וחטאים בעדת צדיקים”
“Therefore the wicked will not stand in judgment, nor sinners in the congregation of the righteous”27.
In this world, the chaff can masquerade as grain. In the world of truth, it cannot. External glitter does not stand up in judgment. Only substance remains.
The final pasuk seals the distinction:
“כי יודע ה׳ דרך צדיקים ודרך רשעים תאבד”
“For Hashem knows the way of the righteous, but the way of the wicked will perish”28.
“Knows” here means more than information. Of course Hashem knows everything. The word carries a sense of attachment and recognition, as in “כי ידעתיו” said about Avraham29.
Hashem is connected to the way of the tzaddik because that way is real and enduring. It is worthy of a relationship. The way of the rasha perishes because it never becomes anything lasting.
Rav Moshe Dovid Vali30 explains that this “knowing” means that Hashem’s holiness cleaves to the path of the tzaddik, because it is ישר and aligned with Him. Love and attachment exist only between similar things.
The term “knowing”, when used regarding Hashem, refers to an intimate form of attachment. Therefore, the tzaddik endures, because holiness attaches itself to him. The path of the wicked is the opposite. It is disconnected from that holiness, and therefore it cannot endure. This is why the pasuk speaks about the “way” of each. The way of the tzaddik is itself something real and enduring. The way of the rasha is not—it falls away.
The Ramdu31 explains that this path of the wicked is tied to the Sitra Achra, which will ultimately be removed when Hashem completes the final tikkun. Rashi understands that these pesukim refer to the final judgment, at the time of Milchemes Gog u’Magog. At that point, everything is brought to truth. Only what is connected to what is real, what is rooted in Torah and spiritual accomplishment, remains. The reshaim, having no inner substance, will not stand.
The beginning of Tehillim tells us exactly how the whole sefer works.
There are only two kinds of people. One is rooted and the other is weightless.
One builds something real, through Torah, alignment, and inner work until it becomes who he is. The other can look impressive for a moment, but there is nothing holding him down. The wind comes and he is gone.
There is no middle. You are either a tree or you are chaff, already being carried by the wind.
Mishnas Reb Aharon – Tehillim
Kovetz Maamarim, vol. 1, p. 318
Avodah Zarah 19a
Avodah Zarah 18b; Yalkut Shimoni— Tehillim 614
Avodah Zarah 18b
Bava Basra 16a
Tehillim - Tinyana
Eis Lechenena, vol. 1, pg. 485
Tehillim - Tinyana
Tehillim - Tlisa
Tehillim 1:2
Tehillim - Tlisa
Tehillim 1:2; based on Avodah Zarah 19a
Avodah Zarah 19a
Ohr HaChama 1
Tehillim - Tinyana
Likutei Halachos, Krias Shema 4:10
Tehillim 1:3
Tehillim - Tinyana
Chomas Enech
see Chomas Enech ibid
Tehillim - Tinyana
Likutei Halachos, Hilchos Shabbos 7:74
Tehillim - Tlisa
Tehillim 1:4
Tehillim - Tlisa
Tehillim 1:5
Tehillim 1:6
Bereishis 18:19
Tehillim - Tinyana
Tehillim - Tinyana
Oh! Thank you for the Targum translation of Ashrei!
“The Targum translates Ashrei as טוביה דגבר, “the good of man.” A person is considered good when he is spiritually aligned.”
So much better than “happy”.
Read this slowly for an hour; it is uplifting to think about.
The word עמד corresponds to asiyah, machshavah, and dibbur.
🤯