Where does the custom of the “tossing of the sandal” in Ruth come from? Why/How does it come to symbolize a successful business transaction?

Question

Everybody loves a good Levirate Marriage story. Personally, I prefer the Ruth story over Tamar's (though that's interesting as well). But I have questions regarding the "sandal tossing" custom found in the Ruth passage. I cited the passage below of the process by which Ruth and her inheritance was given over to Boaz:

Now this was the custom in former time in Israel concerning redeeming and concerning exchanging, to confirm all things: a man drew off his shoe, and gave it to his neighbour; and this was the attestation in Israel.-- So the near kinsman said unto Boaz: 'Buy it for thyself.' And he drew off his shoe. And Boaz said unto the elders, and unto all the people: 'Ye are witnesses this day, that I have bought all that was Elimelech's, and all that was Chilion's and Mahlon's, of the hand of Naomi. Moreover Ruth the Moabitess, the wife of Mahlon, have I acquired to be my wife, to raise up the name of the dead upon his inheritance, that the name of the dead be not cut off from among his brethren, and from the gate of his place; ye are witnesses this day. Ruth 4:7-10

1. Where does this custom come from?
2. Was this common in ancient negotiations/contracts? It seems from the text that the scribes felt they needed to explain to the readers that this was done according to "the manner in [a] former.. time" as if the readers would be unfamiliar with it too.
3. Do we have any other sources, biblical or not, which report a similar incident?
4. Are you aware of any scholarly articles that comment or elaborate on this elusive custom?
5. How/Why does a tossing of a sandal come to represent "Nice doing business with you?"
6. What does the tossing of the sandal symbolize?

Thanks! (You can't see me, but I'm tossing a sandal at you).

Answer 1

In Devarim 25:5-10, we find the direct commandment for "tossing the sandal":

If brothers reside together, and one of them dies having no son, the dead man's wife shall not marry an outsider. [Rather,] her husband's brother shall be intimate with her, making her a wife for himself, thus performing the obligation of a husband's brother with her [...] so that his name shall not be obliterated from Israel.

But if the man does not wish to take his brother's wife, the brother's wife shall go up to the gate, to the elders, and say, "My husband's brother has refused to perpetuate his brother's name in Israel he does not wish to perform the obligation of a husband's brother with me." Then the elders of his city shall call him and speak to him, and he shall stand up and say, "I do not wish to take her."

Then his brother's wife shall approach him before the eyes of the elders and remove his shoe from his foot. And she shall spit before his face and answer [him] and say, "Thus shall be done to the man who will not build up his brother's household!" And that family shall be called in Israel, "The family of the one whose shoe was removed."

Aside from the story of Tamar and Er found in Bereishit 38, I could not find any other occasions. The practice was phased out by the times of the Talmud, thus we find in Bechorot 13a:

חליצה בראשונה שהיו מתכוונין לשם מצוה ועכשיו שאין מתכוונין לשם מצוה אמרו מצות חליצה קודמת למצות יבום מצות הגאולה באדון הוא קודם לכל אדם שנאמר (ויקרא כז, כז) ואם לא יגאל ונמכר בערכך:

Essentially stating that the practice of Yibbum should be phased out in favor of Halitza. (Sorry for my inability to translate, but that fact can be confirmed by the Jewish Encyclopedia's page on the matter and other reputable sources)

In terms of scholarly articles, one in the Journal of Biblical Literature can be found here and accessed in full by making a free account. Feel free to read it yourself, but it essentially offers two leading opinions:

1. Sandals symbolized authority, thus removing them showed the widow's freedom from her brother-in-law's "authority" over her as future husband.

2. Tied in to removing shoes when in mourning, if the brother-in-law refuses to continue on his brother's line, the death becomes even more of a hardship.

Possible reasoning for tossing a sandal after a business deal would thus be related to the ceding of authority. As land was very valuable, removing ones sandals after completing a land transaction was equivalent to ceding one's "authority" over the land. By voluntarily handing over this symbol of authority, it could easily show happiness and willingness in regards to a transaction.

Answer 2

The verse of Megilat Ruth you quoted is largely explained in Gemara Baba Metsia 47a&b. The discussion is about the mode of transaction called Chalipin, i.e. excange, used in business, for barter and sale. This practice is still used nowadays. A deed of sale is very often manifested by this, called "Kinyan Chalipin".

כתנאי (רות ד) וזאת לפנים בישראל על הגאולה ועל התמורה לקיים כל דבר _שלף איש נעלו ונתן לרעהו__

גאולה זו מכירה וכן הוא אומר (ויקרא כז) לא יגאל

Redeeming is sale

תמורה זו חליפין וכן הוא אומר (ויקרא כז) לא יחליפנו ולא ימיר אותו

exchanging is barter

לקיים כל דבר שלף איש נעלו ונתן לרעהו מי נתן למי בועז נתן לגואל רבי יהודה אומר גואל נתן לבועז

תנא קונין בכלי tool אע"פ שאין בו שוה פרוטה אמר רב נחמן לא שנו אלא בכלי אבל בפירי לא רב ששת אמר אפילו בפירות מאי טעמא דרב נחמן אמר קרא נעלו נעל אין מידי אחרינא לא מאי טעמיה דרב ששת אמר קרא לקיים כל דבר לרב נחמן נמי הכתיב לקיים כל דבר ההוא לקיים כל דבר דנקנין במנעל ורב ששת נמי הכתיב נעלו אמר לך רב ששת מה נעלו דבר המסויים en entire object אף כל דבר המסויים לאפוקי חצי רמון וחצי אגוז דלא אמר רב ששת בריה דרב אידי כמאן כתבינן האידנא במנא דכשר למקניא ביה במנא לאפוקי מדרב ששת דאמר קונין בפירות דכשר לאפוקי מדשמואל דאמר קונין דף מז,ב גמרא במרוקא

From the verses we learn which object is regular for the Kinyan Chalipin, tool, whole object, not half object, according to diverses opinions.

למקניא לאפוקי מדלוי דאמר בכליו של מקנה tool from the seller or from the buyer קמ"ל למקניא ולא לקנויי ביה רב פפא אמר למעוטי מטבע ורב זביד ואיתימא רב אשי אמר למעוטי איסורי הנאה איכא דאמרי ביה אמר רב פפא למעוטי מטבע not a coin דכשר אמר רב זביד ואיתימא רב אשי למעוטי איסורי הנאה אבל מוריקא לא אצטריך:

They discute too if the seller or the buyer provides this object. See English translation of the Gemara