The letter Ayin is the 16th letter of the Aleph-Bet, having the numeric value of 70. The pictograph for Ayin looks something like an eye, whereas the classical Hebrew script (Ketav Ashurit) is constructed of a Yod (with a descending line) and embedded Zayin.
From the Canaanite pictograph, the letter morphed into the Phoenician /ketav Ivri , to the Greek letter Omicron, which eventually became the Latin letter "O."
The Meaning of Ayin The word Ayin means "eye," "to see," and by extension, to understand and obey (see Jer. 5:21, Isa. 6:10, Matt. 13:15, etc.). Ayin further represents the primeval light, that is, the spiritual light of God mentioned in Gen. 1:3 (in distinction to celestial lights mentioned in Gen. 1:14-18). According to Jewish midrash, this divine light is far greater than the light that emanates from the sun and stars. Though concealed in the Torah, the spiritual eye can behold the presence of this radiance, but only by means of inner eye given by the Ruach HaKodesh.
Allegories of Ayin Ayin is sometimes described as having two eyes that connect to a common "optic nerve" that leads to the brain. The two eyes represent choice or the actions of the will (i.e., the heart). We can choose whether to use the good eye or the evil eye to perceive things; we can choose to see the glass as half full rather than half empty.
Ayin (like the letter Aleph) is a silent letter. It is said that Ayin "sees" but does not speak, and therefore represents the attitude of humility (or anavah). Anavah begins with an Ayin, as does the word for service (avodah) and yoke (ol). On the other hand, Ayin can represent idolatry (avodah zara) as well as slavery (avedut), both of which are born out of the heart of envy.
When the eye is evil (ayin ra), it becomes a slave to the purposes of sin and the yetzer hara (the evil impulse). As Rashi said, "The heart and the eyes are the spies of the body: they lead a person to transgress; the eyes see, the heart covets, and the body transgresses (Bamidbar 15.39).
A person is said to be olam katan (Χ’ΧΦΉΧΦΈΧ Χ§ΦΈΧΦΈΧ), a miniature world. The eye reflects the world outside and reveals the world inside. A person's outlook reveals their inner character. This is part of what Jesus meant when He said, "The eye is the light of the body. So, if your eye is healthy, your whole body will be full of light, but if your eye is evil, your whole body will be full of darkness. If then the light in you is darkness, how great is the darkness!" (Matt. 6:22-23).
According to the Talmud (Shabbat 104a), the good eye of Ayin looks toward Samekh in the alphabet and stands for the acronym semokh ("support") anaiyim ("the poor"). That is, the ayin tovah ("good eye") will manifest itself in benevolence and charity toward others. On the other hand, the ayin hara ("evil eye") will look to the letter Pey (mouth), considering how it might consume for itself in greed and envy.
The Gematria of Ayin The letter Ayin can be represented as the number 16 (from its ordinal position within the Alphabet), as 17 (from its component values of Yod (10) and Zayin (7)); as 70 (from its number within the alphabet), as 130 (from its plenary spelling: Ayin (70), Yod (10), and Nun (50)), and so on. The value 130 is thought to be suggestive of the ladder (selum) of Sinai, both words which equal 130, which suggests that the spiritual eye sees the Torah as the means of approaching God.
Of particular interest, however, is the number 70, since it occurs frequently within Scripture and Jewish tradition. In Scripture we read that 70 souls went into Egypt, 70 elders of Israel saw the God of Israel on Mt. Sinai, 70 sacrifices made for the nations (during the festival of Sukkot), and Israel was subject to 70 years of exile in Babylon. In Jewish tradition, there are 70 members of the Sanhedrin, 70 words of Kaddish, 70 "faces of Torah," 70 Names of God, and 70 birth pangs until the coming of the Mashiach.
The Eye(s) of the LORD In the Scriptures, God's intimate knowledge of our lives is sometimes referred to as the "Eye of the Lord." Adonai's eyes are in every place, observing both the good and evil (Prov. 15:3). [This is sometimes referred to as hashgachah.] The LORD's eyes focus throughout the whole earth to defend the righteous (2 Chr. 16:9) and to sustain and deliver those who are hoping in His chesed (faithful mercy).
The eyes of the LORD are toward the righteous and his ears toward their cry.
Enlarged Ayin The Ayin of the first word of the Shema is enlarged, perhaps as a reminder that we should both hear (obey) and see (understand) that the LORD God of Israel is the One true God to whom we owe our lives.
Crowned Letters In some Torah Scrolls, eight Hebrew letters are given special adornment by attaching three "tagin" or crownlets to them. Collectively these letters are sometimes called "sha'atnezgets" letters (for Shin, Ayin, Tet, Nun, Zayin, Gimmel, and Tsade).
Midrash ascribes the origin of the tagin as part of mattan Torah - the giving of the Torah at Sinai. The Talmud describes Moses wondering about why God was affixing these embellishments to certain letters of the Torah:
"When Moses went up to God, he found God sitting and putting little crowns on the top of the letters of the Law. He said to God, 'Who is it that forces You to put crowns to the letters of the Law [which You have already written]? He replied, 'A man is to appear on earth after many generations, Akiba b. Joseph by name, who will expound for each top of every letter of the Law heaps and heaps of rulings'...." Talmud (Menachot 29b)
Some people have wondered if these crownlets are the "tittles" referred to by Jesus in Matthew 5:18, although it is unclear that the tagin were in use at that time. It is more likely that the "tittle" refers to the "kots" or "thorn" that projects from a letter.