Yeshua was an Easterner, not a Westerner, and his way of thinking was much less abstract than is ours; he taught in word-pictures rather than 3-point PowerPoint presentations. The two miracles recorded in the Gospel accounts of Yeshua feeding first a crowd of 5000, and then a crowd of 4000, were a word-picture to his followers, who tended to see symbolism in many aspects of their everyday lives.
The first miracle, involving the feeding of 5000 with five loaves and two fish, took place in a very Jewish place, near Bethsaida (Luke 9:10). Beth, in Hebrew, means "house", and "sayid" means, essentially, "box lunch". They're about to eat at the Box Lunch Restaurant. (God loves wordplay, but we Gentiles miss out on so much of it.)
Numbers to the Jewish mindset nearly always have symbolic value. The number 5 would cause a Hebrew mind to conjure up ideas of God's grace and/or the Five Books of the Torah ("Pentateuch"), and 1000 (as in 5 x 1000) would suggest a very "completeness". Two would remind them of the two witnesses in Deuteronomy. The crossing over the sea into this desert just before the meal, at the Passover season, would have them thinking in terms of Moses leading the Israelites through the Red Sea and into the wilderness. The crowds were instructed to sit in groups of fifties and 100's, again reminiscent of the time Moses' father-in-law suggested that he appoint judges over the people in groups of 1000's, 100's, fifties, and tens. The twelve baskets of leftovers would trigger thoughts of the twelve tribes of Israel. The whole event would have the people thinking such thoughts as, "Is this the promised Prophet like Moses, feeding "manna" to us, the Messiah who will free us Israelites from our overlords?"
And then just a few days later, Yeshua is in a very Gentile place near the pagan cities of Tyre and Sidon (Matt 15:21). Here he fed 4000 people with seven loaves of bread and a few fish, and collected seven baskets of leftovers. The number four represented the four-corners of the earth, or in Jewish-think, the gentile nations of the world, and the sevens represented a divine completeness. All-in-all, this event had the people thinking, "Man, this party sure seems to have a lot of Gentile elements to it." (The "few" fish, being unspecified, merely highlights the symbolism of the other numbers which are reported.)
Later, the Jewish mind which reflected back on these two events suddenly realized: "Jesus, the bread of life, born in "Bakery-ville" ("Beth" = house; lehem = bread; Bethlehem = "House of Bread"), is feeding both Jew and Gentile, bringing the two groups into one family, nurturing them with the complete Torah of God."