The Last Supper was after preparations for the Passover and Feast of Unleavened Things. No leaven was in the upper room! (See Exodus 12:15,19.) Unleavened bread, etc. has symbolic meaning at this feast. Yeast is absolutely excluded. But refusing alcoholic drinks always has practical benefits: so that you can distinguish between the holy and unholy (Leviticus 10:10).
Let’s look at the Greek words at the Last Supper, at the beginning of the crucifixion, and finally at the end of the crucifixion:
1. At the Last Supper: none of the gospels use the word wine (oinos). He gave “the fruit of the vine” (gennematos tes ampelou) at the Last Supper (Matt. 26:29; Mark 14:25; Luke 22:18).
2. At the beginning of the crucifixion: Jesus refused the vinegar (oxos) that was mixed with poison (chole) (Matt 27:34). Like Matthew 27:34, the Septuagint also says both chole and oxos in Psalm 69:21. Luke 23:36 says vinegar (oxos). Mark 15:23 says Jesus refused wine that had bitterness (oinos smurnizo) at the beginning of the crucifixion. Mark’s gospel does not later repeat the term “oinos smurnizo” – nor even wine (oinos).
3. Later, near the end of the crucifixion: Jesus accepted plain vinegar (oxos) when He said, “I thirst”. John 19:29-30 says vinegar (oxos). Matt 27:48 and Mark 15:36 also say vinegar (oxos) not wine (oinos). This time it was not mixed with poison. So this time He accepted plain vinegar.
It is misleading and unfortunate that the Contemporary English Version incorrectly puts “wine” when it should say “vinegar” in John 19:29-30. This is the plain vinegar that Jesus accepted near the end of the crucifixion. Unlike most versions, the CEV also puts “wine” in Luke 22:18 at the Last Supper where it should say “the fruit of the vine”. Even though the original Greek has no contradiction, the CEV misleads its reader to wrongly suppose Jesus broke His own word. Never!
Luke 22:18 CEV “I tell you that I will not drink any more wine until God’s kingdom comes.” [Note: gennematos tes ampelou – should say “the fruit of the vine”.]
John 19:30 CEV “After Jesus drank the wine, he said, ‘Everything is done!’ He bowed his head and died.” [Note: oxos – should say “vinegar”.]
Luke 22:18 WEB “For I tell you, I will not drink at all again from the fruit of the vine, until God’s Kingdom comes.”
John 19:30 WEB “When Jesus therefore had received the vinegar, he said, ‘It is finished.’ He bowed his head, and gave up his spirit.”
“Purge out the old yeast, that you may be a new lump, even as you are unleavened. For indeed Christ, our Passover, has been sacrificed in our place. Therefore let’s keep the feast, not with old yeast, neither with the yeast of malice and wickedness, but with the unleavened … of sincerity and truth. I wrote to you in my letter to have no company with sexual sinners; yet not at all meaning with the sexual sinners of this world, or with the covetous and extortionists, or with idolaters; for then you would have to leave the world. But as it is, I wrote to you not to associate with anyone who is called a brother who is a sexual sinner, or covetous, or an idolater, or a slanderer, or a drunkard, or an extortionist. Don’t even eat with such a person.” (1 Cor. 5:7-11 WEB) [Note: the word bread (artos) is absent from verse 8 in the Greek text itself. This is why Young’s Literal Translations says “unleavened food of sincerity and truth” – not talking about bread only, but all unleavened things.]
P.S. Though wine (oinos) was sometimes intoxicating wine and sometimes non-intoxicating wine, none of the gospels use the word wine (oinos) at the Last Supper anyway. Moreover, at Corinth: when methuo is in a context where it contrasts with hunger (1 Cor. 11:21), in this case it merely indicates satisfaction. Compare Jer. 31:25 where the Septuagint says methuo. “For I have satiated the weary soul, and I have replenished every sorrowful soul.” (Jer. 31:25) So in 1 Cor. 11:21, methuo is not intoxication because in this specific instance because is not here being contrasted to sobriety. Rather, in this instance it is being contrasted to hunger.
In any case, it seems rather bizarre for some people to finally resort to Paul’s rebuke of the Corinthians when they today demand we should use alcohol in a holy sacrament. Will the same people insist Jesus broke His own word in John 19:30 if they themselves suppose alcoholic wine were at the Last Supper too – where Jesus said: “the fruit of the vine”?
Plain vinegar is not called the fruit of the vine, and neither is intoxicating. But alcohol intoxicates, as it is a mocker (Prov 20:1).
Jewish details on Passover and Calvary
“…I looked for some to take pity, but there was none; for comforters, but I found none. They also gave me gall for my food…” (Psalm 69:20-21) Gall (rosh in Hebrew) is a word used in the Old Testament. It sometimes describes the venom of snakes (Deut. 32:33; Job 20:16). Jesus refused the offer! (Matt. 27:34)
Encyclopedia of World Cultures, 1996, Karaites, ‘Passover is a very central holiday for Egyptian Karaites because it serves as an allegory for their own historical exodus from Egypt. During the Passover seder, or meal, which is only held one night, the Karaites read from their own Haggadah that retells the story of the hasty departure of the Jews from Egypt in biblical times. Instead of wine, they drink a homemade grape juice from red, seedless raisins because they say that the juice would not have had an opportunity to ferment, and they eat bitter herbs and lamb. During Passover week, Karaites refrain from eating leavened bread, anything derived from soaked grains, or food prepared outside of the home.’
Accidental fermentation was preventable. See: “Some ancient wines not even mildly intoxicating. Others were intoxicating.”
The New Covenant
“But he was pierced for our transgressions. He was crushed for our iniquities. The punishment that brought our peace was on him; and by his wounds we are healed.” (Isa. 53:5) Christ’s blood is the blood of the New Covenant. To “cut off” means to make a spotless sacrificial covenant (or else to punish someone not fearing God by not taking His covenant seriously). See also Ex. 24:8; Ps. 50:5; Ps. 89:3; Isa. 55:3; Jer. 31:31; 32:40; 34:18; Dan. 9:26.
“Therefore whoever eats this bread or drinks the Lord’s cup in a way unworthy of the Lord will be guilty of the body and the blood of the Lord.
But let a man examine himself, and so let him eat of the bread, and drink of the cup.
For he who eats and drinks in an unworthy way eats and drinks judgment to himself, if he doesn’t discern the Lord’s body.” (1 Cor. 11:27-29)