I. Four Stages of Selling Chametz
The practice of selling chametz to remove it from Jewish ownership on Pesach has gone through four historical stages, according to Rav Shlomo Yosef Zevin (Ha-Mo’adim Ba-Halachah, Pesach, ch.4). We may be witnessing the development of a fifth. The first stage was individuals permanently selling their chametz to gentiles; the second was selling and then repurchasing it after the holiday; the third was, additionally, selling it without removing it from the Jew’s house; and the fourth was authorizing a rabbi to conduct the entire sale and repurchase on behalf of the community. Each stage was controversial but took hold with the support of major halachic authorities.
The fourth stage — the communal sale by the rabbi — was extremely controversial because the further an individual Jew is removed from the sale, the more of a formality and less of a true transfer the sale can become. If you are not even selling the chametz directly to a gentile, there is a greater chance you may not really intend to sell it and are you just performing a ritual.
II. Distance and Sales
According to many authorities, selling one’s chametz is a loophole — a ha’aramah — which like an eruv can only function within rabbinic prohibitions, not biblically proscribed food (or carrying). Some contend that the recitation of the bitul formula, nullifying all chametz in your possession, satisifies the biblical requirement and thereby allows the sale. Others only allow the sale of chametz mixtures that are rabbinically forbidden.
Despite the rabbinic rather than biblical context, authorities require the seller to utilize multiple forms of property transfer and specially worded contracts when food is not transferred from the Jew’s property (see Sha’arei Teshuvah 448:5). The complexity of the transaction demands expertise — hence the development of a communal sale by a rabbi. While this further distances the seller from the transaction, the benefit gained by having an expert seller conduct the procedure takes precedence.
In the fourth stage of sales, which has dominated for over a century, individuals appoint a rabbi as an agent to sell the chametz. Each individual is technically the seller but the rabbi serves as an agent for many people and conducts one communal sale on behalf of all those who appointed him.
III. Click and Sell
In recent years, we have witnessed a new development — internet sales of chametz. This entails the seller entering address and other information on a web form and clicking on a button to appoint a rabbi — sometimes unspecified — as an agent to sell chametz. Without seeing or even speaking to the rabbi performing the sale, the seller is even further removed from the transaction. Does this work?
Technically, one may appoint an agent merely by stating that you are appointing him (Shulchan Aruch, Choshen Mishpat 182:1). However, the Rambam (Mishneh Torah, Hilchos Mechirah 5:12-13) records a custom to solidify an appointment of an agent by making a kinyan sudar. In this way, the Rambam says, you make clear that you truly want to appoint this agent to act on your behalf. The Rambam adds that if you say “I wholeheartedly said and decided this,” you have satisfied the custom.
We normally follow this custom only when appointing a rabbi as an agent to sell chametz, not when otherwise appointing an agent. Presumably, this is because of the danger inherent in the distance of the seller from the actual sale. When it comes to chametz, even if only rabbinically forbidden, we try to strengthen the agency and minimize the risk of the sale becoming a mere ritual.
IV. Long Distance Sales
Authorities of the past have allowed appointment of a rabbi to sell chametz over the phone, when necessary (Piskei Teshuvos ch. 448 n. 72). The custom of making a kinyan sudar can be set aside under extenuating circumstances. However, Rav Hershel Schachter says in the name of Rav Joseph B. Soloveitchik that, in keeping with the Rambam’s words, the telephoner should state that he appoints the rabbi “wholeheartedly” (Nefesh Ha-Rav, p. 179). This fulfills the custom without the in-person kinyan sudar.
Sales on the internet further remove the seller from the transaction and provide convenience but no halachic benefit. Additionally, these sales do not allow for the custom of making a kinyan sudar. For these reasons, it seems to me that these sales are not optimal. They work but should be a last resort.
If you cannot appoint a rabbi as an agent in person or over the phone, only then should you appoint a rabbi as your agent via the internet. That rabbi should preferably identify himself on the webpage and include a checkbox specifying that the seller appoints the rabbi “wholeheartedly.”
Is this the start of a new method? Will the internet change the sale of chametz like it has changed so much else? In this case, I think it will only be to the detriment of the user, who will increase the risk of turning a religously-motivated transaction into a perfunctory, religious ritual. When your role in selling your chametz is reduced to fifteen seconds and click, it will be a less serious exercise.