1)

which PROPERTY OF TZADIKIM IS DESTROYED?

ת"ר (דברים יג) החרם אותה ואת כל אשר בה פרט לנכסי צדיקים שבחוצה לה ואת כל אשר בה לרבות נכסי צדיקים שבתוכה. שללה ולא שלל שמים ואת כל שללה לרבות נכסי רשעים שחוצה לה. א"ר שמעון מפני מה אמרה תורה נכסי צדיקים שבתוכה יאבדו מי גרם להם שידורו בתוכה ממונם לפיכך ממונם אבד
Translation: A Beraisa taught, "Hacharem Osah" excludes property outside the city that belongs to Tzadikim of the city. "V'Es Kol Asher Bah" includes Tzadikim's property inside the city. "Shelalah (its spoils)", but not Shelal Shamayim. "V'Es Kol Shelalah" includes property outside the city that belongs to Resha'im of the city. R. Shimon said, why did the Torah say that Tzadikim's property inside the city is destroyed? What caused them to live in the city? Their money. Therefore, their money is destroyed.
(a)

Why do we need a Drashah to teach about Tzadikim's property inside the city?

1.

Iyun Yakov: Since they did not sin, it should be considered Shelal Shamayim, which is not burned.

(b)

"Shelalah" should exclude Resha'im's property outside the city!

1.

Rashi (according to Rashash), Iyun Yakov: "Kol Shelalah" includes it.

(c)

What is the law of animals and slaves of Tzadikim in the city?

1.

Daf Al ha'Daf citing Over Orach (128): Rav Avraham ha'Kohen was unsure; perhaps a Rasha's animal is killed due to its owner's evil. I see no reason for doubt. The Torah included Nichsei Tzadikim like Nichsei Resha'im! Surely we do not kill an Eved Kena'ani, for one is Chayav Misah for killing him. However, I am unsure about a Nochri slave who is not an Eved Kena'ani, even of a Rasha. I later saw that Minchas Chinuch (464:20) discusses slaves. (He says that we kill the Eved Kena'ani of a Rasha, just like we kill his wife and animals, but not of a Tzadik.)

(d)

May Tzadikim of the city leave dressed, or are their clothes burned?

1.

Daf Al ha'Daf citing Pardes Yosef ha'Chadash (Re'eh): Rashi (Erchin 7b) learns from here that they leave naked; their clothes are burned. Our Gemara did not discuss this. This implies that they leave clothed! Beis Yitzchak (OC 14:7) says so. The Rambam did not discuss this; the Lechem Mishneh and Minchas Chinuch say that he holds like Rashi; the Chazon Ish (Sanhedrin 24:15) disagrees, Beis Yitzchak (ibid. 10) brought from his son that Kevod ha'Beriyos overrides even a Lav in the Torah, so they leave clothed.

(e)

Why did R. Shimon give the reason why Tzadikim's property inside the city is destroyed?

1.

Rashi: R. Shimon always explains the reasons for Mitzvos.

i.

Margoliyos ha'Yam 17: The Zohar says that wherever Resha'im live is destroyed. One should always live where people of good deeds live.

2.

Iyun Yakov: Since "Shelalah" excludes [Shelal Shamayim], one might have thought that also Tzadikim's property is excluded.