In Matthew 14:13-21, Jesus fed five thousand people with a small collection of fish and bread. Then in 15:32-39, he fed four thousand people with another small collection of fish and bread. Matthew 16 references these two stories and draws important lessons about the two feedings. My suggestion is that in Matthew 16, Jesus asks questions in a way that shows the significance of the numbers of baskets leftover in Matthew 14 and 15. I think those real numbers have a symbolic meaning.
In Matthew 16, the disciples are in a boat with Jesus and they’ve forgotten to bring the leftover bread (Matt. 16:5). Jesus warned them of the leaven (or teaching) of the Pharisees and Sadducees (16:6, 12), but the disciples were too distracted by the lack of actual bread in the boat (16:7-8).
Jesus helps them focus by asking some questions in Matthew 16:9-10. In 16:9 he asks, “Do you not remember the five loaves for the five thousand, and how many baskets you gathered?” And in 16:10, “Or the seven loaves for the four thousand, and how many baskets you gathered?”
Notice the information Jesus supplied. He refers to both feedings (which are reported in Matt. 14:13-21 and 15:32-39), the number of loaves in each case (“five” in the first feeding, “seven” in the second), and the number of people who were present for each miracle (“five thousand” and “four thousand,” respectively). However, there is also a number Jesus omits in each question: “how many baskets you gathered” (16:9 and 16:10). The reader has already learned that 12 baskets of leftovers were gathered after the first feeding, and 7 baskets after the second (see 14:20 and 15:37). When Jesus was on the boat with the disciples in Matthew 16, he surely knew the number of baskets that were leftover in each episode, so he didn’t ask for those figures for his own information. The phrasing of the questions in 16:9 and 16:10 highlights the number of leftovers because it was the only number Jesus didn’t explicitly give in each question. Jesus wanted the disciples to recall the number of the baskets when he fed the 5,000 and the number of the baskets when he fed the 4,000.
Notice that the numbers of baskets are not random numbers like 9 or 17 or 22. The numbers are 12 and 7, which are significant numbers in Scripture. Some interpreters may be reluctant to ascribe symbolic significance to the number of baskets in Matthew 14 and 15, but I think the phrasing of Jesus’ questions in 16:9 and 16:10 invites the reader to consider a meaning to the numbers. If the numbers didn’t matter, why omit those details in the questions? Jesus clearly wants the specific numbers to be remembered. Because of the geographical areas where the feedings in Matthew 14 and 15 took place, the former was probably a “Jewish” feeding, reinforced by the “12” baskets of leftover bread (for Israel had 12 tribes in the Old Testament), and the latter was probably a “Gentile” feeding, reinforced by the “7” baskets of leftover bread (for Deut. 7:1 names seven nations in Canaan; and note too that Jesus had just healed a Canaanite woman’s daughter in Matt. 15:21-28 before the second miraculous feeding).
In the miraculous feedings of Matthew 14 and 15, Jesus was forecasting the great messianic feast, where Jewish and Gentile believers would fellowship with their God forever. He himself was the Bread of Life (see John 6:22-41), the true and better Moses. The two feedings showed that Jesus was reconstituting the people of God around himself. He was the one who would provide what they needed, no matter if they were Jews or Gentiles. He not only gave them bread, he would be bread for them. In the fields, he gave them loaves. On the cross, he gave himself.