Judges and Order (or the lack of it).

Our story begins after most of the drama in the book of Judges. Or does it?

(ג) וַיָּקָם אַחֲרָיו יָאִיר הַגִּלְעָדִי וַיִּשְׁפֹּט אֶת יִשְׂרָאֵל עֶשְׂרִים וּשְׁתַּיִם שָׁנָה. (ד) וַיְהִי לוֹ שְׁלֹשִׁים בָּנִים רֹכְבִים עַל שְׁלֹשִׁים עֲיָרִים וּשְׁלֹשִׁים עֲיָרִים לָהֶם לָהֶם יִקְרְאוּ חַוֹּת יָאִיר עַד הַיּוֹם הַזֶּה אֲשֶׁר בְּאֶרֶץ הַגִּלְעָד.

Judges 10:3-4

(3) And after him arose Jair, the Gileadite; and he judged Israel twenty and two years. (4) And he had thirty sons that rode on thirty ass colts, and they had thirty cities, which are called Havvoth-jair unto this day, which are in the land of Gilead.

דברים ג׳:י״ד

(יד) יָאִיר בֶּן מְנַשֶּׁה לָקַח אֶת כָּל חֶבֶל אַרְגֹּב עַד גְּבוּל הַגְּשׁוּרִי וְהַמַּעֲכָתִי וַיִּקְרָא אֹתָם עַל שְׁמוֹ אֶת הַבָּשָׁן חַוֹּת יָאִיר עַד הַיּוֹם הַזֶּה.

Deuteronomy 3:14

(14) Jair the son of Manasseh took all the region of Argob, unto the border of the Geshurites and the Maacathites, and called them, even Bashan, after his own name, Havvoth-jair, unto this day.—

What is happening? Yair, supposedly 250 years after the conquest of the land, is mentioned before that event?

This is not an isolated event. Other judges, in the same part of the book as Yair, are also mentioned in Torah.

שופטים י׳:א׳

(א) וַיָּקָם אַחֲרֵי אֲבִימֶלֶךְ לְהוֹשִׁיעַ אֶת יִשְׂרָאֵל תּוֹלָע בֶּן פּוּאָה בֶּן דּוֹדוֹ אִישׁ יִשָּׂשכָר וְהוּא יֹשֵׁב בְּשָׁמִיר בְּהַר אֶפְרָיִם.

Judges 10:1

(1) And after Abimelech there arose to save Israel Tola the son of Puah, the son of Dodo, a man of Issachar; and he dwelt in Shamir in the hill-country of Ephraim.

דברי הימים א ז׳:א׳

(א) וְלִבְנֵי יִשָׂשכָר תּוֹלָע וּפוּאָה ישיב [יָשׁוּב] וְשִׁמְרוֹן אַרְבָּעָה.

I Chronicles 7:1

(1) And of the sons of Issachar: Tola, and Puah, Jashub, and Shimron, four.

במדבר כ״ו:כ״ג

(כג) בְּנֵי יִשָּׂשכָר לְמִשְׁפְּחֹתָם תּוֹלָע מִשְׁפַּחַת הַתּוֹלָעִי לְפֻוָה מִשְׁפַּחַת הַפּוּנִי.

Numbers 26:23

(23) The sons of Issachar after their families: of Tola, the family of the Tolaites; of Puvah, the family of the Punites;

שופטים י״ב:י״א

(יא) וַיִּשְׁפֹּט אַחֲרָיו אֶת יִשְׂרָאֵל אֵילוֹן הַזְּבוּלֹנִי וַיִּשְׁפֹּט אֶת יִשְׂרָאֵל עֶשֶׂר שָׁנִים.

Judges 12:11

(11) And after him Elon the Zebulunite judged Israel; and he judged Israel ten years.

במדבר כ״ו:כ״ו

(כו) בְּנֵי זְבוּלֻן לְמִשְׁפְּחֹתָם לְסֶרֶד מִשְׁפַּחַת הַסַּרְדִּי לְאֵלוֹן מִשְׁפַּחַת הָאֵלֹנִי לְיַחְלְאֵל מִשְׁפַּחַת הַיַּחְלְאֵלִי.

Numbers 26:26

(26) The sons of Zebulun after their families: of Sered, the family of the Seredites; of Elon, the family of the Elonites; of Jahleel, the family of the Jahleelites.

Shoftim, according to many scholars, is out of chronological order. But how is it possible that these regnants correspond to the journeys in the desert?

שמות י״ח:כ״ה

(כה) וַיִּבְחַר מֹשֶׁה אַנְשֵׁי חַיִל מִכָּל יִשְׂרָאֵל וַיִּתֵּן אֹתָם רָאשִׁים עַל הָעָם שָׂרֵי אֲלָפִים שָׂרֵי מֵאוֹת שָׂרֵי חֲמִשִּׁים וְשָׂרֵי עֲשָׂרֹת.

Exodus 18:25

(25) And Moses chose able men out of all Israel, and made them heads over the people, rulers of thousands, rulers of hundreds, rulers of fifties, and rulers of tens.

The only suggestion that I can think of is that these forgotten rulers became the judges, leading over their respective tribes and assisting in the capture of the land after Moshe.

יהושע י״א:כ״א-כ״ג

(כא) וַיָּבֹא יְהוֹשֻׁעַ בָּעֵת הַהִיא וַיַּכְרֵת אֶת הָעֲנָקִים מִן הָהָר מִן חֶבְרוֹן מִן דְּבִר מִן עֲנָב וּמִכֹּל הַר יְהוּדָה וּמִכֹּל הַר יִשְׂרָאֵל עִם עָרֵיהֶם הֶחֱרִימָם יְהוֹשֻׁעַ. (כב) לֹא נוֹתַר עֲנָקִים בְּאֶרֶץ בְּנֵי יִשְׂרָאֵל רַק בְּעַזָּה בְּגַת וּבְאַשְׁדּוֹד נִשְׁאָרוּ. (כג) וַיִּקַּח יְהוֹשֻׁעַ אֶת כָּל הָאָרֶץ כְּכֹל אֲשֶׁר דִּבֶּר יְהוָה אֶל מֹשֶׁה וַיִּתְּנָהּ יְהוֹשֻׁעַ לְנַחֲלָה לְיִשְׂרָאֵל כְּמַחְלְקֹתָם לְשִׁבְטֵיהֶם וְהָאָרֶץ שָׁקְטָה מִמִּלְחָמָה.

Joshua 11:21-23

(21) And Joshua came at that time, and cut off the Anakim from the hill-country, from Hebron, from Debir, from Anab, and from all the hill-country of Judah, and from all the hill-country of Israel; Joshua utterly destroyed them with their cities. (22) There was none of the Anakim left in the land of the children of Israel; only in Gaza, in Gath, and in Ashdod, did some remain. (23) So Joshua took the whole land, according to all that the LORD spoke unto Moses; and Joshua gave it for an inheritance unto Israel according to their divisions by their tribes. And the land had rest from war.

Notice that the first places mentioned are Hevron and Devir, which are both part of the story of Calev and Othniel in Judges 3. The next general area mentioned are the Judean Mountains, which were Ehud's (and possibly Shamgar's) base of operation. Finally, we move on to the Israelite Mountains, probably synonymous with Har Ephraim; it's southern parts are home to Devorah, it's center is Gidon's base, and the final judges normally come from it's northern outskirts.
Also, the only places spared are the Philistine cities; at the end of Judges, they are still Israel's overlords.

Could this mean that the Judges were contemporary to Joshua? Maybe. But the subject is wide open for debate, Ad She'Yavo Eliyahu. If anyone has other ideas, don't hold back from making source sheets to explain your thoughts (One request: Write what you mean in comments. It kills me when people just leave a bunch of sources on a page, as if I'm telepathic)!