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צֶ֥דֶק צֶ֖דֶק תִּרְדֹּ֑ף לְמַ֤עַן תִּֽחְיֶה֙ וְיָרַשְׁתָּ֣ אֶת־הָאָ֔רֶץ אֲשֶׁר־יְהוָ֥ה אֱלֹהֶ֖יךָ נֹתֵ֥ן לָֽךְ׃ (ס)

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Rashi on Deuteronomy

צדק צדק תרדף JUSTICE, JUSTICE SHALT THOU PURSUE — go to (search after) a reliable court (Sifrei Devarim 144:14; Sanhedrin 32b).
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Ramban on Deuteronomy

JUSTICE, JUSTICE SHALT THOU PURSUE. “Go to seek a reliable court. THAT THOU MAYEST LIVE, AND INHERIT THE LAND. The appointment of qualified judges is of sufficient [importance] to sustain Israel and to settle them upon their Land.” This is Rashi’s language quoting from the Sifre.17Sifre, Shoftim 144. The reason for the repetition [of the word “justice”] is to indicate that the judges should judge the people with righteous judgment,18Verse 18. and you must also pursue justice constantly by going from your place to the place of the great Sages: “after Rabban19The title “Rabban” indicates that he was the chief of the Sanhedrin. Rabban Yochanan ben Zaccai served as the chief of the Sanhedrin immediately following the destruction of the Second Temple. It was he who obtained permission from Vespasian to be “given Jabneh and its Sages.” It was there, in Jabneh, that the centrality of Jewish spiritual authority was reaffirmed after the destruction. See Note 90 further. Yochanan ben Zaccai to Jabneh; after Rabbi [Yehudah Hanasi] to Beth Shearim.”20This city in the Lower Galilee served as the center wherein “Rabbi” and all the Sages of the generation compiled the entire Mishnah.
And Rabbi Abraham [ibn Ezra] commented: “Justice, justice. It is mentioned twice in order to indicate that one should pursue justice whether it would be to his advantage or loss. Or [it may be mentioned] one time after another for emphasis.” But in the Midrash of Rabbi Nechunya ben Hakanah21Sefer Habahir 74. See Vol. I, 24, Note 42. the Rabbis interpreted it by way of a secret. They said: “Justice — this is His attribute of justice in the world, as it is said, Justice, justice shalt thou pursue. After that it is written, that thou mayest live, and inherit the Land. If you will judge yourself [knowing whence you came, and whither you are going, and before Whom you are about to give account and reckoning]22So explained by Abusaula. you will live. If not, He will judge you and affirm [His judgment over you] against your will. And why is justice mentioned twice? Because it is written, from the brightness before Him.23II Samuel 22:13. The verse continues: coals of fire flamed forth. The two terms brightness and fire thus refer to these two aspects of justice (Abusaula). The first justice refers to actual justice, this being the Divine Glory, as it is written, righteousness lodges in her.24Isaiah 1:21. And what is the second justice? It is that which frightens the righteous” [making them fearful that perhaps they do not merit the World to Come].25Abusaula. See also Vol. I, p. 401 that such is the nature of the righteous. And there [in that Midrash] it is further explained:26Sefer Habahir 75.Justice is the helmet of salvation upon His head.27Isaiah 59:17. The ‘head’ denotes only truth, as it is said, The beginning of Thy word is truth,28Psalms 119:160. and ‘truth’ is peace, as it is said, Is it not so, if peace and truth shall be in my days?29II Kings 20:19. etc.” If so, Scripture is stating here, “You are to judge in your court [to attain] justice, and pursue therein justice and [try to] achieve it, that thou mayest live in the World to Come with the second justice [which alludes to Him]30Abusaula. Who is the Higher Justice, this being the great light hidden for the righteous for the Time to Come, and this is also the Might of the Holy One, blessed be He; and thou shalt inherit the Land, the Land of Israel, with the first justice.”
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Sforno on Deuteronomy

צדק צדק תרדוף. When you are about to put this legislation into practice, the party in charge of appointing such judges is told by Moses to select only those who are already known for their sense of fair play and righteousness. He will have to look for such people all over the tribe. If potential judges do not have all the qualifications which are desirable in a judge, this qualification of fairness is the overriding quality all must possess. This is what the prophet Samuel was told by G’d when he had to look for a replacement of King Sha-ul among the sons of Yishai. (Samuel I 16,7) He was specifically told to ignore external appearances.
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Or HaChaim on Deuteronomy

צדק צדק תרדף, "Righteousness, righteousness shall you pursue, etc." This is a warning to you that if in one city there can be found two exceedingly wise men and two other men also ordained but not as brilliant as the first two, you should not say that seeing both are competent you will not bother the brilliant ones with your little problem but instead submit it for judgment to the lesser sages. You should always seek out the most renowned judge (scholar) to act as judge in any litigation you are involved in.
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Tur HaArokh

צדק, צדק תרדוף, “Righteousness, righteousness, you shall pursue!” According to Nachmanides the reason why Moses repeated the word צדק here is to exhort not only the judges to pursue righteousness but also the ordinary citizen to pursue every avenue to ensure that public affairs are run on a basis of righteousness. Judges appointed to a court must be people possessed of a blameless reputation. [Sodom also had judges, but what judges! Ed.] Ibn Ezra writes that the reason the word appears twice is to teach that righteousness must be pursued regardless of whether it results in one’s advantage or even if it is liable to result in one’s disadvantage. Alternately, Moses repeated the word to encourage you to make this pursuit something that is not restricted to a one-time effort, but to urge to keep striving for righteousness.
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Rabbeinu Bahya

צדק צדק תרדוף, “Righteousness, righteousness, you shall pursue.” According to the plain meaning of the text the Torah warns (by repeating) that one must strive to be righteous both in word and in deed. These are the two ways in which one may potentially inflict harm upon both oneself and upon others. Everyone who speaks righteously reflects the fact that his deeds are most likely righteous also; this is why it behooves every Jew to be both righteous in his speech and in his deeds. This sentiment is reflected in Tzefaniah 3,13 when he said of the remnant of the people of Israel that “they shall do no wrong or speak falsehood; a deceitful tongue shall not be in their mouths.”
Alternatively, our verse addresses the people who are subject to litigation and exhorts them to strive for righteousness regardless of whether this will be financially beneficial or harmful to them. This is why the Torah repeats the exhortation.
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Siftei Chakhamim

Follow after the pre-eminent tribunal. Explanation: even though any tribunal can judge a defendant against his will, nevertheless, it is a mitzvah for the claimant to go after a pre-eminent tribunal. Because you cannot define [the verse] according to its simple meaning [that the judges must pursue justice], because if so it should have said “judge [absolute justice].” Also, why is צדק written twice, [whereas now the verse means, pursue justice that is righteous]. And also it is already written, “Do not pervert justice.” Rather, “Go after, etc.”
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Rav Hirsch on Torah

V. 20. צדק צדק תרדף. Als höchstes einziges, rein um seiner selbst willen anzustrebendes Ziel, dem alle anderen Rücksichten sich unterzuordnen haben, soll der nationalen Gesamtheit צדק, das "Recht", die Gestaltung aller Einzel- und Gesamtverhältnisse nach den Anforderungen des göttlichen Gesetzes vorschweben. Dieses Ziel unablässig mit aller Hingebung zu verfolgen, ist Israels einzige Aufgabe, למען תחיה וירשת usw. damit hat er alles getan, um seine physische (תחיה) und politische Existenz sicher sich stellen. Indem hier das durch die Rechtshuldigung und (וירשת) Rechtspflege zu schaffende politische Glück selbst nach der bereits vollzogenen Besitznahme des Landes — und von einer solchen Zeit spricht ja offenbar der Text — immer noch וירשת ירושה genannt wird, ist damit wohl die bedeutsame Wahrheit niedergelegt, dass der Besitz des Landes in jedem Augenblick in Frage gestellt und es in jedem Augenblick durch die vom jüdischen Staatsganzen dem Rechte zu zollende Huldigung und Verwirklichung aufs neue in Besitz zu nehmen ist. Sanhedrin 32 b wird die Wiederholung des צדק צדק in unserem Satze noch dahin erläutert, dass damit einer jeden richterlichen Tätigkeit, auch der nicht entscheidenden, sondern ausgleichenden, das unparteiliche Recht als Richtschnur gegeben wird. צדק צדק תרדף אחד לדין ואחד לפשרה. Auch bei פשרה, bei dem Vergleich, den zu versuchen Sanhedrin 6 a מצוה לבצוע, bei jeder zivilrechtlichen Streitsache Mizwa ist, soll der vermittelnde Richter keine der Parteien bevorzugen.
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Chizkuni

צדק צדק תרדוף, “Justice, Justice, you are to pursue;” here too the Torah addresses the litigants.
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Rashi on Deuteronomy

למען תחיה וירשת [JUSTICE, JUSTICE SHALT THOU PURSUE] THAT THOU MAYEST LIVE, AND INHERIT [THE LAND WHICH THE LORD THY GOD GIVETH THEE] — The appointment of honest judges is sufficient merit to keep Israel in life and to settle them in security in their land (Sifrei Devarim 144:15).
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Sforno on Deuteronomy

למען תחיה וירשת, such qualities are of even greater importance in the Land of Israel, as a failure to comply would result in the ancestral right to that country being denied to you. Compare Isaiah 57,17 who quotes G’d as telling him that a corrupt judiciary [getting away with sinful greed? Ed.] was a primary cause for G’d’s anger at the people.
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Rabbeinu Bahya

A kabbalistic approach, based on Nachmanides: the reason for repeating the word צדק is that the Torah reminds you that righteousness emanates from the emanation צדק. It promises the judge that if he strives to dispense the kind of justice which reflects righteousness, he in turn will be the recipient of input from that emanation. It is something like Exodus 15,16 where Moses prayed (in the song) תפול עליהם אימתה ופחד, “may fear and trepidation fall upon them” (the Gentile nations). The letter ה at the end of the word אימתה which is not really necessary, is an allusion to the final letter ה in the tetragrammaton, the source of this fear in the part of the tetragrammaton which represents the attribute of Justice. [Being imbued with such fear of the attribute צדק is not a threat but a promise in this instance. It is as if judges who practice righteousness will be rewarded with יראת שמים as a result. Ed.]. You will find this approach echoed in the Sefer Habahir items 74-75 where the author, in commenting on the sequence of צדק צדק תרדוף למען תחיה וירשת, explains that the repetition of the word צדק reflects what is written in Psalms 18,13 מנגה נגדו, i.e.[a repetition of נגה and גחלי אש which are two different forms of intense heat, the latter one a weaker reflection of the former one] that the first time the word appears it refers to true righteousness, whereas the second time it is like an echo of the original righteousness practiced. He who strives to perform righteousness will find that it echoes all around him. The reason we call a proselyte who has sought to place himself under the כנפי השכינה, the protective wings of G’d’s presence, a גר צדק is that he has acquired the trepidation for this attribute of Justice which we normally refer to as יראת שמים, “awe of heaven.” [Perhaps this point must be emphasized especially with the convert as he may think that conversion bestows only the welcome acceptance by the attribute of Mercy without simultaneously submitting to G’d as the attribute of Justice. Ed.]. By submitting to that attribute one has embraced Judaism in the full meaning of the word.
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Siftei Chakhamim

There is adequate merit in the appointment of ethical judges, etc. Rashi is answering the question: “Pursue absolute justice,” [meaning] follow after the pre-eminent tribunal, is commanded only to someone who has litigation with his fellow, so just for this the entire nation of Yisroel will [merit to] live and inherit the land?! He answers that “so that you may live” does not refer to “Pursue absolute justice” but to “Judges and police officers you shall appoint for yourself, etc.”
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