Who were the Anakim?

In the book of Numbers, chapter 13, the Anakim are introduced to Bible readers. Unlike ourselves as modern Bible readers, the people of Israel were what we call a “high context audience.” They were not just relying on scant written records, they were living out the experience and immersed in the culture. Ancient Israelites had a much better grasp of who the Anakim were than we modern readers have traditionally had. So what did the Israelites know that made them so afraid of the Anakim? Why would the Biblical author connect them with the pre-Flood Nephilim - a word that translates as “giants”?
Israel had just left Egypt and knew of the Anakim from Egyptian interactions with them. Archaeologically, we have evidence of Egyptian contact with the Anakim from the now-famous “Execration Texts.” The purpose of these was a kind of magical ritual for cursing one’s enemies. The fact that Egyptians considered them formidable enough to require sympathetic magic against them tells us that they were no ordinary enemies.
Joshua, as military leader under Moses, was likely of Egyptian heritage (his father’s name “Nun” is probably Egyptian). If anyone in the group was going to be familiar with the Anakim, Joshua was most likely.
Caleb was the other non-Israelite of the group - who as a Kenizzite was familiar with the people groups concerned and not worried about how to deal with them. That’s why he later took their capital Kiriyath Arba (Hebron). The remaining ten spies were faithless in the face of the Anakim and never made it into the Promised Land.
So what’s in a name?
“Anakim” does not mean “long-necked.” That comes from the assumption that Anakim is a word of Hebrew origin. In fact, it has early Egyptian and later Greek derivation, hence the connections with proto-Greek cultures like the Hittites and Hurrians, and later Phoenicians, from which we get Perizzites, Philistines etc.
The royalty connection is exemplified in the Anakim. The Biblical account tells us of some of the kings among the Anakim, the “sons of Anak.” “Anak” is not just a name but also a title, from the Greek anax, meaning, “king.” It is one of the many titles of Apollo, who had a temple in Athens dedicated to the worship of the Anakes, protector gods similar to the Mesopotamian Apkallu. The Bible tells us that the Anakim, or more accurately, ben `anaq, “sons of Anak,” were descended from a man named Arba, father of Anak, after whom was named Kiriath Arba (“city of the tree,” later Hebron). The name “Arba” comes from Arbion, a verdant mountain on the island of Crete featuring a prominent temple to the deity Zeus Arbios (god of the tree). According to the ancient Greek author Pausanius in his work, The Description of Greece, the father of Anax, named Asterius, was said to be at least ten cubits in height. According to Homer, Anax was an archaic title, most suited to legendary heroes and gods rather than for contemporary kings.
Taking it back further, the Egyptian derivation of “anaq” can be traced back to the earliest hieroglyphs. The ankh is a symbol that looks like a Christian cross but with a loop on the top. In its earliest use, it was intended to describe a spirit within a person - not their physical organic life or quality of being alive, but a spirit within the person. This was originally not for the common man, but was used of divinised rulers - in other words, it represented a different spirit which imbued the king with the qualities of the deity. The hieroglyph shows a tree reaching up to touch the sun, and is suggestive of glorification or deification. We see now how it is that the author of Numbers 13:33 was able to say that “the Anakim come of the Nephilim.”
This image is maintained in the Greek use of “Anax,” when we consider Zeus Arbios and the idea of the deified ruler represented by a tree on a mountain that “reaches to heaven.” In the Bible we get this imagery in Ezekiel 31 - a passage that connects us back to that enigmatic character known as “the Assyrian,” or “Nimrod.” He was the guy responsible for a man-made mountain that was built to reach heaven...
Seeing Babel as the origin of royal human deification makes sense of all of these ethnic variations of the concept. It ties in with the worldview that Scripture presents, showing that the nations were subjected to the rule of lesser gods following the rebellion at Babel.
Those who had participated at Babel became the divinised rulers of the nations - imbued with the spirits of the Nephilim and recognised as such by their tall stature. They were known by many tribal names, but collectively they were called Anakim - “the ascended masters.”

- T.J. Steadman