Our story begins after most of the drama in the book of Judges. Or does it?
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.
(א) וַיָּקָם אַחֲרֵי אֲבִימֶלֶךְ לְהוֹשִׁיעַ אֶת יִשְׂרָאֵל תּוֹלָע בֶּן פּוּאָה בֶּן דּוֹדוֹ אִישׁ יִשָּׂשכָר וְהוּא יֹשֵׁב בְּשָׁמִיר בְּהַר אֶפְרָיִם.
(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.
(א) וְלִבְנֵי יִשָׂשכָר תּוֹלָע וּפוּאָה ישיב [יָשׁוּב] וְשִׁמְרוֹן אַרְבָּעָה.
(1) And of the sons of Issachar: Tola, and Puah, Jashub, and Shimron, four.
(כג) בְּנֵי יִשָּׂשכָר לְמִשְׁפְּחֹתָם תּוֹלָע מִשְׁפַּחַת הַתּוֹלָעִי לְפֻוָה מִשְׁפַּחַת הַפּוּנִי.
(23) The sons of Issachar after their families: of Tola, the family of the Tolaites; of Puvah, the family of the Punites;
(יא) וַיִּשְׁפֹּט אַחֲרָיו אֶת יִשְׂרָאֵל אֵילוֹן הַזְּבוּלֹנִי וַיִּשְׁפֹּט אֶת יִשְׂרָאֵל עֶשֶׂר שָׁנִים.
(11) And after him Elon the Zebulunite judged Israel; and he judged Israel ten years.
(כו) בְּנֵי זְבוּלֻן לְמִשְׁפְּחֹתָם לְסֶרֶד מִשְׁפַּחַת הַסַּרְדִּי לְאֵלוֹן מִשְׁפַּחַת הָאֵלֹנִי לְיַחְלְאֵל מִשְׁפַּחַת הַיַּחְלְאֵלִי.
(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?
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.
(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.
(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)!