Both Joseph and Judah are seen as leaders in the book of Genesis. From Joseph being sold to the Midianites, to the confrontation of the brothers and Joseph in Egypt, and to Jacob's blessings to them before his eventual passing, Joseph and Judah demonstrate different but important leadership qualities as they each have moral struggles they have to work through.
The redemptions of both Joseph and Judah as well as the power struggle between the two begs the question: who is the real leader in this story? Is it Joseph, who rises from the vengefulness of his brothers and imprisonment in Egypt? Or is it Judah, who has command of his brothers but lacks the companionship of God that Joseph does?
(26) Then Judah said to his brothers, “What do we gain by killing our brother and covering up his blood?
וַיֹּאמֶר יְהוּדָה אֶל אֶחָיו וגו', אָמַר רַבִּי יְהוּדָה בַּר אִילָעי בִּשְׁבַח יְהוּדָה הַכָּתוּב מְדַבֵּר, בִּשְׁלשָׁה מְקוֹמוֹת דִּבֵּר יְהוּדָה בִּפְנֵי אֶחָיו וְעָשׂוּ אוֹתוֹ מֶלֶךְ עֲלֵיהֶם, וַיֹּאמֶר יְהוּדָה אֶל אֶחָיו, (בראשית מד, יד): וַיָּבֹא יְהוּדָה וְאֶחָיו, (בראשית מד, יח):
(26) "Then Judah said to his brothers.."
Rabbi Yehudah bar Ilai said: Scripture speaks in praise of Judah. In three places Judah spoke before his brothers and they made him king over them. Other examples: "Judah spoke to his brothers..." (Genesis 44:18), "Judah and his brothers went.." (Genesis 44:18)
(ד) וַיְהִי ה' אֶת יוֹסֵף (בראשית לט, ב), הָא עִם שְׁאָר שְׁבָטִים לָאו, אָמַר רַבִּי יוּדָן לְבֶהָמִי שֶׁהָיָה לְפָנָיו שְׁתֵּים עֶשְׂרֵה בְּהֵמוֹת טְעוּנוֹת יַיִן, נִכְנְסָה אַחַת מֵהֶם לַחֲנוּתוֹ שֶׁל עוֹבֵד כּוֹכָבִים, הִנִּיחַ אַחַת עֶשְׂרֵה וְהָלַךְ לוֹ אַחֲרֶיהָ, אָמְרוּ לוֹ מַה אַתָּה מַנִּיחַ אַחַת עֶשְׂרֵה וְהוֹלֵךְ לְךָ אַחֲרֵי הָאֶחָת, אָמַר לָהֶם, אֵלּוּ בִּרְשׁוּת הָרַבִּים הֵם וְאֵינִי חוֹשֵׁשׁ לָהֶן שֶׁמָּא יֵעָשֶׂה יַיִן נָסֶךְ. כָּךְ אֵלּוּ גְּדוֹלִים וּבִרְשׁוּת אֲבִיהֶם, אֲבָל זֶה שֶׁהוּא קָטָן וּבִרְשׁוּת עַצְמוֹ, לְפִיכָךְ וַיְהִי ה' אֶת יוֹסֵף.
"The Lord was with Joseph.." But not with the other tribal ancestors? Rabbi Judan said: This may be compared to a drover who had 12 cows before him laden with wine. One of them entered a shop belonging to a Gentile, whereupon he (the left the eleven and followed this one. On being asked, 'Why do you leave the eleven and follow this one?' He replied; 'These are in the street, and I am not afraid lest they should render the wine nesek (idolatrous, used for idols); but as for the one which has entered the Gentile's shop, I fear that he may render the wine nesek.' Similarly, these others were grown up and they were under their father's control; but this one (Joseph) was young and his own master. Therefore, "And the Lord was with Joseph."
(ה) וַיִּגַּשׁ אֵלָיו יְהוּדָה, (עמוס ט, יג): הִנֵּה יָמִים בָּאִים נְאֻם ה' וְנִגַּשׁ חוֹרֵשׁ וגו', חוֹרֵשׁ, זֶה יְהוּדָה. בַּקּוֹצֵר, זֶה יוֹסֵף, שֶׁנֶּאֱמַר (בראשית לז, ז): וְהִנֵּה אֲנַחְנוּ מְאַלְּמִים אֲלֻמִּים. (עמוס ט, יג): וְדֹרֵךְ עֲנָבִים, זֶה יְהוּדָה, (זכריה ט, יג): כִּי דָרַכְתִּי לִי יְהוּדָה קֶשֶׁת. (עמוס ט, יג): בְּמשֵׁךְ הַזָּרַע, זֶה יוֹסֵף, שֶׁמָּשַׁךְ זַרְעוֹ שֶׁל אָבִיו וְהוֹרִידוֹ לְמִצְרַיִם, כְּדִכְתִיב (הושע יא, ד): בְּחַבְלֵי אָדָם אֶמְשְׁכֵם. (יואל ד, יח): יִטְפוּ הֶהָרִים עָסִיס, אֵלּוּ הַשְּׁבָטִים, אָמְרוּ מְלָכִים מִדַּיְנִים אֵלּוּ עִם אֵלּוּ אָנוּ מָה אִכְפַּת לָנוּ.
"Then Judah went up to him..." 'Behold, the days come, said the Lord, that the plowman shall overtake the reaper' (Amos 9:13). 'The plowman shall overtake' alludes to Judah; 'The reaper,' to Joseph, as it says, 'For, behold, we were binding sheaves, etc. (Genesis 37:7). 'And the treader of grapes' (Zachariah 9:13) alludes to Judah, as it says, 'For I have trodden Judah for Me' (Amos 9:13); 'Him that soweth the seed' refers to Joseph who drew his father's seed and brought them down to Egypt' (Hosea 11:4). 'And the mountains shall drop sweet wine, etc.' alludes to the tribal ancestors, who exclaimed, 'When kings contend with each other, what had it do with us? It is fitting for a king to contend with a king!'
Although both Judah and Joseph demonstrate leadership qualities in their own right, each get very different types of blessings from their father Jacob before his death. Judah is blessed with a future kingdom and the Messianic lineage while Joseph, Jacob's most beloved son, is blessed with eternal help from God. In these two blessings we see the difference between Judah and Joseph's leadership; the former is one that is grounded amongst the people and has the ability to work amongst humans while the latter is one of divine nature and facilitates his authority through communication with God.
(כב) בֵּ֤ן פֹּרָת֙ יוֹסֵ֔ף בֵּ֥ן פֹּרָ֖ת עֲלֵי־עָ֑יִן בָּנ֕וֹת צָעֲדָ֖ה עֲלֵי־שֽׁוּר׃ (כג) וַֽיְמָרֲרֻ֖הוּ וָרֹ֑בּוּ וַֽיִּשְׂטְמֻ֖הוּ בַּעֲלֵ֥י חִצִּֽים׃ (כד) וַתֵּ֤שֶׁב בְּאֵיתָן֙ קַשְׁתּ֔וֹ וַיָּפֹ֖זּוּ זְרֹעֵ֣י יָדָ֑יו מִידֵי֙ אֲבִ֣יר יַעֲקֹ֔ב מִשָּׁ֥ם רֹעֶ֖ה אֶ֥בֶן יִשְׂרָאֵֽל׃ (כה) מֵאֵ֨ל אָבִ֜יךָ וְיַעְזְרֶ֗ךָּ וְאֵ֤ת שַׁדַּי֙ וִיבָ֣רְכֶ֔ךָּ בִּרְכֹ֤ת שָׁמַ֙יִם֙ מֵעָ֔ל בִּרְכֹ֥ת תְּה֖וֹם רֹבֶ֣צֶת תָּ֑חַת בִּרְכֹ֥ת שָׁדַ֖יִם וָרָֽחַם׃ (כו) בִּרְכֹ֣ת אָבִ֗יךָ גָּֽבְרוּ֙ עַל־בִּרְכֹ֣ת הוֹרַ֔י עַֽד־תַּאֲוַ֖ת גִּבְעֹ֣ת עוֹלָ֑ם תִּֽהְיֶ֙ין֙ לְרֹ֣אשׁ יוֹסֵ֔ף וּלְקָדְקֹ֖ד נְזִ֥יר אֶחָֽיו׃ (פ)
(22) Joseph is a wild ass, A wild ass by a spring —Wild colts on a hillside. (23) Archers bitterly assailed him; They shot at him and harried him. (24) Yet his bow stayed taut, And his arms were made firm By the hands of the Mighty One of Jacob— There, the Shepherd, the Rock of Israel— (25) The God of your father who helps you, And Shaddai who blesses you With blessings of heaven above, Blessings of the deep that couches below, Blessings of the breast and womb. (26) The blessings of your father Surpass the blessings of my ancestors, To the utmost bounds of the eternal hills. May they rest on the head of Joseph, On the brow of the elect of his brothers.