(Lev. 25:25:) WHEN YOUR BROTHER BECOMES POOR, etc. This is what Scripture says (Ps. 106:43): MANY TIMES HE DELIVERED THEM, etc., [AND THEY BECAME POOR THROUGH THEIR INIQUITY]. You find that in the days when the judges judged, Israel was serving idolatry, and they were enslaved into the hands of the nations of the world, as it is said (Judges 3:7): AND THE CHILDREN OF ISRAEL DID EVIL, etc. And what did they do? (Judges 3:9:) AND THE CHILDREN OF ISRAEL CRIED OUT TO THE LORD, AND THE LORD RAISED UP A SAVIOR FOR THE CHILDREN OF ISRAEL [AND HE SAVED THEM], namely Othniel ben Kenaz. Immediately they repented and were redeemed. So too another time, [as it is said] (Judges 3:12): AND THE CHILDREN OF ISRAEL AGAIN DID EVIL, AND THE LORD STRENGTHENED EGLON, etc. [Immediately they repented,] and He raised up for them a redeemer, Ehud [ben Gera, and they were redeemed through him]. And again they served idolatry, and they were sold into the hand of Sisera, as it is said (Judges 4:3): AND HE OPPRESSED THE CHILDREN OF ISRAEL WITH MIGHT. What is the meaning of WITH MIGHT? R. Shimon ben Levi said: With revilings and with blasphemies, as you say (Mal. 3:13): YOUR WORDS HAVE BEEN MIGHTY AGAINST ME. Once they repented, He raised up for them as redeemers Deborah and Barak, [and they were redeemed through them]. Thus (Ps. 106:43): MANY TIMES HE DELIVERED THEM, etc., AND THEY BECAME POOR THROUGH THEIR INIQUITY. What is the meaning of AND THEY BECAME POOR THROUGH THEIR INIQUITY? That they became impoverished among the nations, as it is said (Judges 6:6): AND ISRAEL BECAME VERY IMPOVERISHED, etc. What is the meaning of AND ISRAEL BECAME IMPOVERISHED? R. Yitzchak and R. Levi: one said that they became impoverished of good deeds, and one said that they did not have enough even to bring a poor person's offering, as it is said (Lev. 14:21): AND IF HE IS POOR [AND HIS MEANS DO NOT SUFFICE, etc.]. Thus, AND THEY BECAME POOR, for they became impoverished.
Why Israel Sank Into Poverty in the Days of the Judges
Midrash Tanchuma Buber, Behar 7:1
וכי ימוך אחריך וגו'. זש"ה פעמים רבות יצילם וגו' [וימוכו בעונם] (תהלים קו מג), אתה מוצא בימי שפוט השופטים שהיו ישראל עובדים ע"ז, והיו משועבדים בידי אומות העולם, שנאמר ויעשו בני ישראל הרע וגו' (שופטים ג ז), ומה עשו, ויזעקו בני ישראל אל ה' ויקם ה' מושיע לבני ישראל [ויושיעם] את עתניאל בן קנז (שם שם ט), מיד עשו תשובה ונגאלו, כך פעם אחרת, [שנאמר] ויוסיפו בני ישראל לעשות הרע ויחזק ה' את עגלון וגו' (שם שם יב), [מיד עשו תשובה] והעמיד להם גואל (ועשו תשובה) את אהוד [בן גרא ונגאלו על ידו], ועוד עבדו ע"ז, ונמכרו ביד סיסרא, שנאמר והוא לחץ את בני ישראל בחזקה (שם ד ג), מהו בחזקה, אמר ר' שמעון בן לוי בחרופין ובגדופין, כד"א חזקו עלי דבריכם (מלאכי ג יג), כיון שעשו תשובה העמיד להם גואלים דבורה וברק [ונגאלו על ידם], הוי פעמים רבות יצילם וגו' וימוכו בעונם (תהלים שם), מהו וימכו בעונם, שנעשו דלים בתוך האומות, שנאמר וידל ישראל מאד וגו' (שופטים ו ו), מהו וידל, ר' יצחק ור' לוי, חד אמר שהיו דלים ממעשים טובים, וחד אמר שלא היה להם להביא אפילו קרבן דל, שנאמר ואם דל הוא [ואין ידו משגת וגו'] (ויקרא יד כא), הוי וימוכו, שנעשו דלים.