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The Gemara (גמרא) rules that Ashkelon requires saying "bifnei nafsha" twice before reciting terumah blessings. Tosafos (תוספות) (via Rabbeinu Tam) explains Ashkelon lacks the sanctity of Eretz Yisrael because Olei Bavel didn't conquer it, yet adds that no beis din or talmidei chachamim reside there. Why the second reason if the first already excludes it from Eretz Yisrael status?
The shiur explores a perplexing element in Tosafos (תוספות) on Gittin 2a regarding the status of Ashkelon. The Mishna rules that in Ashkelon, one must recite "bifnei nafsha" (in my own presence) twice before making a blessing on terumah, a stringency that normally applies only outside Eretz Yisrael. This raises an obvious question: pesukim in Tanach clearly indicate that Ashkelon was within the boundaries of Eretz Yisrael and was actually conquered by the Jewish people. Tosafos addresses this question by bringing two distinct proofs. First, Tosafos cites a pasuk using the language "hanesharim" (that which was left over), indicating that Ashkelon was within the designated boundaries of Eretz Yisrael—land that should have been captured. Second, Tosafos brings a pasuk from Sefer Shoftim proving that they actually did conquer the land. The shiur asks: why does Tosafos need both proofs? Why not simply cite the second pasuk showing that the land was conquered?
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Gittin 2a
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