Came out stripped of his assets/ to lose all one's property/ down to the last farthing
Lost all his money or property; ended up with nothing left.
("Shimon ben Zoma says: So-and-so came out stripped of his assets—and has no benefit from them at all"—Pesachim 22b; and likewise: "It was only the sins that caused a fire to break out in the city, and his house went up in flames, and he came out stripped of his assets, with only his shirt on his back"—Shalom Aleichem / Nachat Avot, 175; and likewise: "His business affairs were thrown into disarray, the wheel of his fortune sank lower and lower, and he came out stripped of his assets. Of all his property, not even a shoelace remained, and his house was empty of everything"—Mordechai ben Yechezkel / Sefer HaMa'asiyot, Part Four, The Barefoot Tzaddik, 93)
Translation
Expression (Hebrew)
יָצָא נָקִי מִנְּכָסָיו
Definition (Hebrew)
אִיבֵּד אֶת כַּסְפּוֹ אוֹ רְכוּשׁוֹ. סִיֵּים עִנְיָן כְּשֶׁאֵין לוֹ יוֹתֵר אֶת רְכוּשׁוֹ.
("שִׁמְעוֹן בֶּן זוֹמָא אוֹמֵר:יָצָא פְּלוֹנִי נָקִי מִנְּכָסָיו-וְאֵין לוֹ בָּהֶם הֲנָאָה שֶׁל כְּלוּם"-פְּסָחִים כב ע"ב, וְכֵן:"אֶלָּא שֶׁגָּרְמוּ הָעֲווֹנוֹת וְנָפְלָה דְּלֵקָה בָּעִיר, וְעָלָה בֵּיתוֹ בָּאֵשׁ, וְיָצָא נָקִי מִנְּכָסָיו, רַק כֻּתָּנְתּוֹ לְעוֹרוֹ"- שָׁלוֹם עֲלֵיכֶם/ נַחַת אָבוֹת, קעה, וְכֵן:"דַּרְכֵי מִסְחָרוֹ נִשְׁתַּבְּשׁוּ, גַּלְגַּל מַזָּלוֹ יָרַד מַטָּה מַטָּה, וְיָצָא נָקִי מִנְּכָסָיו. מִכָּל רְכוּשׁוֹ לֹא נִשְׁאַר אַף שְׂרוֹךְ נַעַל, וּבֵיתוֹ רֵיקָם מִכָּל"- מָרְדְּכַי בֶּן יְחֶזְקֵאל/ סֵפֶר הַמַּעֲשִׂיּוֹת חֵלֶק רְבִיעִי, הַצַּדִּיק הַיָּחֵף, 93)