This week we begin Masechet Demai. Demai refers to produce that has been purchased from an Am Haaretz -- one not versed in the laws of separating terumot and maaserot. The Gemara (Sotah 48a) explains that Yochanan Kohen Gadol surveyed and found that while everyone separated terumah gedolah (the first ~2% given to the kohen), a substantial1 minority did not separate any of the other maaserot. Consequently, to enable continued commerce and interaction, he decreed that any produce purchased from an am Haaretz would be considered Demai. The classification meant that the remaining maaserot still needed to be separated. Nevertheless, since there was a doubt whether the separation was necessary, many leniencies were built into Demai. Similarly, some of the separated maaserot could be retained by the owners. These leniencies will be covered over the course of the masechet.
The second Mishnah discusses the leniencies afforded to maaser sheni of demai. The second maaser in the first, second, fourth and fifth year of the shemittah cycle is maaser sheni. That maaser should be taken to Yerushalaim and consumed there. One however can transfer the sanctity to money and take that money to yerushalaim and purchase food there instead. If one however does so, they must add "chomesh". While chomesh literally means a fifth, it is really a quarter of the value of the food that one wishes to redeem (since the addition is a fifth of the total sum used for redemption). We learn in the second Mishnah that one of the leniencies of the demai is that one does not need to add chomesh when redeeming maaser sheni of demai. We shall try to understand why.
The Bartenura explains that the reason chomesh is not required is because, on biblical level, not adding chomesh when redeeming maaser sheni does not prevent the redemption from taking effect. The Gemara (Bava Metzia 54b) records Ravina who explains that had chomesh been required as part of this gezeirah, there was a risk that people would disregard maaser sheni of demai altogether.
How then do we understand the requirement of adding chomesh? We find the requirement to add chomesh in other areas also, about which we will learn -- redemption of hekdesh, arachin, one who stole and swore falsely regarding his possession of the article, etc. The Mishnah Rishona explains that when the Torah discusses the keren (principle) it uses different terminology to the chomesh. When referring the keren, the Torah uses the words ve'shilem (and he must pay) or ve'hechzir (he must return). With respect to chomesh the wording is ve'natan (and he shall give). It appears to suggest that the chomesh does not act as part of the redemption but rather a "matana", a form of gift.3
1 The Tosfot Yom Tov (1:1) explains that even though we normally are not concerned about the minority, this case is different since here the minority was substantial and widespread.
2 Note that doubt alone does not afford this leniency. See Derech Emunah (Maaser Sheni 5:26) who explains that if one purchased produce from one that is suspected of not separating maaserot, then chomesh would need to be added. This is based on the Chazon Ish (4:14), who explains that demai is different since the doubt is me'ikar ha'din. Similarly, the Derech Emunah continues that nowadays, since most do not separate maaserot the leniencies of demai do not apply. The same is true in other cases of doubt or maaser sheni derabannan.
3 The exception to this distinction between keren and chomesh is the obligation of payment placed on a non-kohen that consumes terumah. See "Is Chomesh a Kapara" (Volume 13, Issue 28).
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