Lot remembered for his bad choices

Lot looked up and saw that the entire Jordan Plain, all the way to Tzoar, had plenty of water. It was like G-d’s own garden, like the land of Egypt. Lot chose for himself the entire Jordan Plain. He headed eastward, and the two separated. Abram lived in the land of Canaan, while Lot dwelt in the cities of the Plain, having migrated as far as Sodom. But the people of Sodom were very wicked, and they sinned against G-d. (13:10-13)

From one perspective, Avram’s nephew Lot is viewed as a positive, albeit tragic, figure. We credit him with the trait of hakhnosas orchim that he learned from his uncle, and the rabbis believed Lot was eventually a judge in Sodom. There were rules about how Ammon and Moav (Lot’s sons conceived through an incestuous relationship) were to be treated by Moshe and the conquering Israelites on account of the familial relationship, which were only cancelled when Moav attacked Israel in Bamidbar 24, as described in Devarim 2:9, as well as the historical note of Sichon having conquered those lands (see Bamidbar 21:26), making them available to Israel to conquer from Sichon.

When the midrash considers the Torah description of Lot’s choice to move to Sodom, however, Lot is portrayed in a different light.

Rabbi Yosi bar Chanina explained that the verse “Lot looked up and saw that the entire Jordan Plain, all the way to Tzoar had plenty of water,” alludes to ervah (lewdness). He raised his eyes, just as Potiphar’s wife raised her eyes to gaze upon Yosef, he saw the kikar Hayarden just as one desires a kikar of bread for the sake of a licentious woman (Mishlei 6:26). Sodom had water – it was all mashkeh – just as the sotah (woman accused of adultery), was to be given to drink (hishkah). Lot saw this before G-d destroyed (shachet) the land, and the term shichet refers to the spilling of seed that was the cause of the death of Onan, son of Yehuda, in Bereshit 38:9.  (Bereshit Raba 41:7)

The Talmud Nazir 23a and other midrashic texts utilize different verses to make similar points about Lot’s proclivities.