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The Gemara (Yevamos 108b) says:

אמר רב יהודה אמר רב מאי דכתיב מימינו בכסף שתינו עצינו במחיר יבאו בשעת הסכנה נתבקשה הלכה זו הרי שיצאה מראשון בגט ומשני במיאון מהו שתחזור לראשון שכרו אדם אחד בארבע מאות זוז ושאלו את ר' עקיבא בבית האסורין ואסר את רבי יהודה בן בתירה בנציבין ואסר

Who taught [the two respective statements of our Mishnah]?27 Rab Judah replied in the name of Rab: To this may be applied the Scriptural text,28 We have drunk our water for money; our wood cometh to us for price.29 In the time of proscription30 the following halachah was inquired for: If a minor left her first husband with a letter of divorce and her second husband through mi'un, may she return to her first husband? They hired a man for four hundred zuz,31 and [through him] they addressed the enquiry to R. Akiba in prison,32 and he stated that she was forbidden.33 R. Judah b. Bathyra [also was asked] at Nesibis and he too forbade her

Rabbi Yehuda Ben Beseira was active before the Beis Hamikdash was destroyed (As in Pesachim 3b of the story of how the Aramean brought the Pesach Sacrifice). Rabbi Akiva was arrested after the Bar Kochva revolt.

How could they be asked the same question at the same time?

  • Why don't you ask how they could have asked somebody in Jerusalem and in Bavel? But more to the point, R' Akiva lived [most of his life] before the destruction, IIRC. – Danny Schoemann Feb 15 '15 at 8:39
  • @DannySchoemann They sent one messengar to jail and the other to Chu"l. – Shmuel Brin Feb 15 '15 at 18:09
  • so what is your question? – Danny Schoemann Feb 16 '15 at 7:27
  • @DannySchoemann They seem to be different generations – Shmuel Brin Feb 16 '15 at 18:35
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The destruction of the temple was in ~70 CE and the Bar Kochba revolt was ~130 CE. Even if Yehudah Ben Beseira straddled the destruction, it would seem to be a stretch to call him a contemporary of Akiva.

The Yerushalmi Talmud on the story in Pesachim 3b lists him only as Ben Beseira. Since presumably he was living in Israel at the time, this is more correct than the Babylonian. The Rambam identifies "ben Beseira" without a first name as Yehoshua ben Beseira, and NOT Yehudah.

This would certainly fix any difficulties in the timeline, as it's made very clear by this gemara that the two were contemporaries being asked the same question simultaneously, or at least that Yehuda was asked after the sent a messenger to Akiva. Otherwise, what need would there be to ask Akiva if they already had an answer 60 years prior?

There is another resolution: some posit that there were multiple tana'im and amoraim who went by the name Yehudah Ben Beseira. If that were the case, then there is no difficulty posed, as this Yehudah is a different person than the one in Pesachim 3b.

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