The Tribe of Issachar — the name, the blessing and the land
יִשָּׂשכָר
Understanding of the times — the strong servant of a good land

What the tribe was
Issachar, the 'strong ass couching down between two burdens,' saw that rest was good and the land pleasant — the fat Jezreel valley — and bowed his shoulder to bear. What looks at first like a plodding blessing flowers in 1 Chronicles 12:32: 'the children of Issachar were men that had understanding of the times, to know what Israel ought to do.' Patient labour that ripens into discernment; Tola the judge and, in Jewish tradition, many Torah scholars, came from this tribe. Deborah's song pairs Issachar's princes with her own war.
Jacob's blessing — Gen 49:14-15
יִשָּׂשכָ֖ר חֲמֹ֣ר גָּ֑רֶם רֹבֵ֖ץ בֵּ֥ין הַֽמִּשְׁפְּתָֽיִם
Issachar is a strong ass couching down between two burdens:
וַיַּ֤רְא מְנֻחָה֙ כִּ֣י ט֔וֹב וְאֶת הָאָ֖רֶץ כִּ֣י נָעֵ֑מָה וַיֵּ֤ט שִׁכְמוֹ֙ לִסְבֹּ֔ל וַיְהִ֖י לְמַס עֹבֵֽד
And he saw that rest was good, and the land that it was pleasant; and bowed his shoulder to bear, and became a servant unto tribute.
Moses' blessing — Deut 33:18-19
וְלִזְבוּלֻ֣ן אָמַ֔ר שְׂמַ֥ח זְבוּלֻ֖ן בְּצֵאתֶ֑ךָ וְיִשָּׂשכָ֖ר בְּאֹהָלֶֽיךָ
And of Zebulun he said, Rejoice, Zebulun, in thy going out; and, Issachar, in thy tents.
עַמִּים֙ הַר יִקְרָ֔אוּ שָׁ֖ם יִזְבְּח֣וּ זִבְחֵי צֶ֑דֶק כִּ֣י שֶׁ֤פַע יַמִּים֙ יִינָ֔קוּ וּשְׂפוּנֵ֖י טְמ֥וּנֵי חֽוֹל
They shall call the people unto the mountain; there they shall offer sacrifices of righteousness: for they shall suck of the abundance of the seas, and of treasures hid in the sand.
Who came out of Issachar
Tola the judge — Judg 10:1The men who understood the times — 1Chr 12:32Baasha king of Israel — 1Kgs 15:27
Moments in the story
Josh 19:17Couching in the good land
Judg 5:15Issachar's princes with Deborah
1Chr 12:32Understanding of the times
Deut 33:19They shall call the people to the mountain
Every mention
Gen 30:18Gen 35:23Gen 46:13Gen 49:14Exod 1:3Num 1:8Num 1:28Num 1:29Num 2:5Num 7:18Num 10:15Num 13:7Num 26:23Num 26:25Num 34:26Deut 27:12Deut 33:18Josh 17:10Josh 17:11Josh 19:17Josh 19:23Josh 21:6Josh 21:28Judg 5:15Judg 10:11Kgs 4:171Kgs 15:271Chr 2:11Chr 6:471Chr 6:571Chr 7:11Chr 7:51Chr 12:331Chr 12:411Chr 26:51Chr 27:182Chr 30:18Ezek 48:25Ezek 48:26Ezek 48:33
