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So Avraham tells Lot, "we need to separate; if you go right I'll go left, and vice-versa." Lot chose to go to Sdom, which was wicked.

Had Lot chosen otherwise, would Avraham have gone to Sdom?

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As the Sipurno explains, Lot didn't choose any of Avram's alternatives- right or left (north or south). Rather he went from the East (Ai and Bais El were of the cities first attacked by Yehoshua) westward. (Lech Lecha 13:11)

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Not denying Alex's answer from medrish Rabba; but checkmarking just because I like this answer. No offense anyone! – Shalom Oct 20 '10 at 18:38
None taken, of course. But how does Sforno account for the fact that the ככר הירדן is also necessarily on the east side of Eretz Yisrael? (After all, the Jordan River - for which the plain is named - is on that side, and indeed the Jewish People crossed that before reaching Beis El and Ai.) – Alex Oct 20 '10 at 23:02
Good point. 2 options might be: 1) Kikar haYarden may have been west of Ai, despite its name. Canaan was sparsely inhabited compared with Bavel and so the reference points may have been looser. 2) The Yarden may have been rerouted due to mahpeichas Sedom. – YDK Oct 21 '10 at 0:09
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The Midrash (Bereishis Rabbah 41:6) states that in fact Avraham chose his words carefully. If he really meant that he would go left, he would have said ואשמאלה (without the yud); but ואשמאילה really means "I will force you to go left" - because in fact Avraham didn't want to live in Sodom. In other words, he wasn't actually giving Lot the choice of direction.

(Still, though, Lot is blamed for accepting this; he should have told Avraham that he doesn't want to live in Sodom either, and they would have worked out some other arrangement.)

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The mefarshim I saw don't learn that Asmeila is going on Sedom. What is your source that that is pshat in the midrash/ – YDK Oct 20 '10 at 17:48
They all associate "staying to the right" with the Negev, where Avraham wanted to stay. So the implication would seem to be that "going to left" means some area further north, closer to Sodom. – Alex Oct 20 '10 at 20:53
Who is "they all"? – YDK Oct 20 '10 at 23:59
I see it in Etz Yosef. I thought I recalled it from elsewhere too. – Alex Oct 21 '10 at 20:03

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