“You did not eat bread, nor did you drink wine” (D’varim 29:5). Although it is certainly true that because G-d provided “manna from heaven” every day (except Shabbos, which was covered by Friday’s portions) and a well from which they drank water, the Children of Israel didn’t need to “eat bread or drink wine,” is it really true that they never did? What about the food and drink they purchased from Edom and Moav (D’varim 2:28-29)? Or the food purchased from the traveling salesmen from nearby countries (Yoma 75b)? [Even though the Talmud (Sanhedrin 106a) says they drank the Amoni wine offered by the women who tried to seduce them at P’or, it can be suggested that it was only consumed by those who sinned, and none of them were still around now (D’varim 4:3-4).] How can the Torah say they didn’t eat any real bread or drink any wine during the entire 40 years in the desert if they did?
Ramban explains the verse to mean that they couldn’t survive on the real food they bought from others, so even though it’s not literally true that they didn’t eat or drink anything else, the verse only means that it wasn’t their primary source of nourishment. Although this wouldn’t explain not drinking wine since it is not a primary source of nourishment (see Iyun HaParasha #115), it can be suggested that wine was the usual drink during meals, which was not the case in the desert. However, if this verse is supposed to match the previous one (their clothes not wearing out), we would expect both to be taken literally.
Tz’ror Hamor and Chasam Sofer connect this verse with the next one, being victorious over Sichone, suggesting that the point isn’t that they never ate bread or drank wine, but (similar to Ramban) that it wasn’t their normal fare. Bread and wine was thought to provide warriors with strength (Malki Tzedek bringing Avraham bread and wine after his war with the kings to give him back his strength is referenced), and this wasn’t the regular diet of those who fought Sichone, yet they were victorious. Aside from the verse still not being literally true (as they did eat real bread), it seems more closely connected to the previous verse, not the one after it.
Abarbanel (addressing a different question) says the point of the verse is not whether they actually ate bread or drank wine, but that they were not faced with the tasks and distractions of working the land in order to eat/drink them. They didn’t need to plant any fields or vineyards, harvest any grain or grapes, or turn them into bread and wine, thereby allowing them to focus on their spiritual growth.
Besides the verse not being true in a literal sense (as they did eat bread and drink wine, albeit without having to go through the long laborious process of growing them and making them from scratch), the point of the verse seems to be that G-d provided everything for them, not that they didn’t have to work for it.
Malbim (who often builds upon Abarbanel’s approach), adds that G-d’s intent (when He brought them into the desert) was not only that they wouldn’t be distracted by work, but also that they wouldn’t eat physical food, which can be an obstacle to spiritual growth. Instead, G-d provided them with spiritual nourishment that took care of their physical needs as well, allowing them to experience optimal spiritual growth. From this perspective, the point isn’t that they never ate bread or drank wine, but that they didn’t need to, as they could have been fully sustained without buying any real food from others. Nevertheless, a simple reading of the verse is that they actually didn’t eat bread or drink wine, not that they didn’t have to.
Maharil Diskin compares the “bread and wine” here to their earlier complaints (Bamidbar 21:5) about having no “bread and water,” even though there was plenty of water (most of the time) and the manna replaced the bread. Just as their complaint was based on their (unjustified) fear that the food they were eating wasn’t being digested properly (see Rashi), here they were being told that they were able to live on the miraculous food G-d provided despite usually not eating any real food with it to help its digestion. Even though this comes closer to explaining the verse literally than any other approach I have seen, it still doesn’t explain it 100% literally, as rather than meaning “you never ate bread or drank wine,” it means “you remained healthy even though most of the time you didn’t eat bread or drink wine.” More importantly, the point of the verse is changed so drastically that it is unlikely to be its intent. The message is no longer that G-d provided miraculous sustenance the entire 40 years, but that the miraculous food He provided didn’t harm them. The focus of the message would not be any miracle, but that an unjustified fear wasn’t realized, more like an “I told ya so!”
The previous verse (D’varim 29:4) raises a different issue, one worthy of a full discussion; I am only mentioning it here because of one seemingly problematic approach to it. In this verse the nation was told that “your shoe did not wear out,” whereas earlier (8:4) they were told that “your foot did not swell.” Did they wear shoes, or not? If they did, why should their feet have become swollen that this was so extraordinary? If they didn’t, there weren’t any shoes that should have worn out but didn’t! Even if this conundrum can be resolved (such as suggesting that feet normally swell from the amount of walking they did even if in shoes), why was one aspect highlighted the first time and the other the second time?
Tzafnas Pa’anayach reconciles these two verses by saying that the second verse refers to the Tribe of Levi, who were not “pushed away” after the sin of the golden calf, so were still allowed to wear shoes. The rest of the nation, on the other hand, were not allowed to wear shoes because of their state of excommunication. [Even if the excommunication only applied to the first generation, whereas those being addressed now, the next generation, were allowed to wear shoes (see Rashi on D’varim 2:16-17), the point being made is that feet didn’t swell and shoes didn’t wear out the entire 40 years.] Therefore, the first verse was said to the entire nation, who could not wear shoes and yet their feet didn’t swell, while the second verse was said to the Tribe of Levi, who did wear shoes, which didn‘t wear out.
The question this approach begs is why the Kohanim and Levi’im were the only ones being addressed here. Additionally, this paragraph (29:1) starts with Moshe addressing the entire nation, not just the Tribe of Levi. However, this issue is taken care of by a different one, as first it was Moshe doing the talking (29:1-3), with G-d being referred to in the third person, then G-d Himself talks (29:4-5), referring to Himself in the first person, before Moshe takes over again (29:6-8), referring to the nation as “we” (see Chizkuni on 29:5). It can be suggested that Moshe was talking to the entire nation, while G-d (being quoted by Moshe) spoke only to the Kohanim and Levi’im. Nevertheless, we are still left with the question of why G-d’s words to them are inserted into the message being given to the entire nation.
Moshe had just told them that they hadn’t been able to know or understand G-d until that day, at the very end of the 40 years. This was in contrast to the Kohanim and Levi’im, who had attained that level decades earlier, which is why originally Moshe only gave a copy of the Torah to them (see Rashi on 29:3). G-d’s interjection explained how the Tribe of Levi was able to attain that level; because He had led them in the desert for 40 years, removing any obstacle that could have distracted them from their spiritual growth. Their clothes never wore out (including their shoes), they didn’t have to work for their food, and the food they were provided was of a spiritual nature. True, this was an environment that the entire nation was given the opportunity to take advantage of, but only the Tribe of Levi seized it. Therefore, addressing the Tribe of Levi (and only the Tribe of Levi, even though the rest of the nation got the message), G-d told them that their shoes never wore out, and they didn’t eat any (real) bread or drink any wine. (After this interjection to explain why Levi was different, and that the rest of the nation could have done the same, Moshe continued to address the nation.)
Did most of the nation eat bread or drink wine during their travels in the desert? Yes. But the Kohanim and Levi’im didn’t. So when addressing them it could accurately be said that “you did not eat bread, nor did you drink wine.” Neither figuratively, nor literally.