There were 14 generations from Avraham to David, 14 generations from David to the Babylonian Exile and 14 generations from the Babylonian Exile to the Messiah.

The meaning of fourteen is related to the Hebrew characters that represent fourteen, the yod (ten) - י and the dalet (four) - ד. Fourteen is represented as: יד. Yod dalet, in addition to being a number, is also the Hebrew word for “hand” – yad - יד. Fourteen is also the number of joints inthe human hand.

The Hebrew word for friend is yedid - ידיד.

How does one show friendship?

They clasp hands and a hand shake.When you shake hands with your friend, you have two hands together – yad yad. This spells out yedid, “friend.” Yedid has the same numerical value of koach, strength, twenty-eight. When you shake hands, no one has the upper hand, you are both equal.

That is the only way that true friendship can exist, when both parties areequal.ידיד - yedid = Friend
Gematria=28
די – dy - Enough
Gematria=14
יד – Need
Gematria=14
Our Sages teach that the number fourteen symbolizes the "strong hand" or "yad hachzaka" (יד החזקה) of Moshe, who was the recipient of the Torah.

Sefer Yad Hachzaka is also the subtitle of the Mishneh Torah, a code of Jewish law (halakha) by Maimonides.

The Mishneh Torah is regardedas Maimonides' magnum opus. The work consists of fourteen books.Maimonides also wrote a book titled Sefer HaMitzvot (The Book of the Commandments).

 

In the life of Yaaqov,

Yaaqov left his parents' home in Be’er Sheva at age 63, but arrived in Charan 14 years later at age 77.

Our sages explain that for fourteen years Yaaqov hid himself in the home of his ancestor and teacher, Eber (the great-grandson of Shem), where he immersed himself in the study of Torah.

When he completed his studies, Yaaqov worked fourteen years for Rachel. This is where we find the first use of the number fourteen in the Torah:Bereshit (Genesis) 31:41

Thus have I been twenty years in thy house; I served thee fourteen years for thy two daughters, and six years for thy cattle: and thou hast changed my wages ten times.

From previous verses we know that Yaaqov worked seven years to earn Rachel and received Leah. He then worked an additional seven years to acquire Rachel.

The fourteen years are made up of two sets of seven years. Further, these two sets of seven were for the purpose of securing and providing for his wives.This suggests that the meaning of fourteen is: The strong hand of HaShem to acquire and take care of His Beloved Bride.

As Yaaqov worked to secure his brides, So HaShem works with His strong hand to acquire His bride.Rachel was barren for fourteen years before she bore Yaaqov two sons, who became fourteen when they entered Mitzrayim.Bereshit (Genesis) 46:22 These are the sons of Rachel, whom she bore to Yaaqov: all the souls, fourteen.

This pasuk suggests that the care that Yaaqov lavished on his beloved allowed her raise up fourteen children and grandchildren. We know that ten of these grandchildren are the sons of Benyamin. Yosef had two children.

Finally there were her children, Yosef and Benyamin.

Another way to understand the meaning of the number fourteen is to see it as a compound number composed of the ‘ten’ part and the ‘four’ part.

Yod = Ten = Ten Words = Torah; Dalet = Four = Four Good news = Grace

As we have seen, in Hebrew the number fourteen is also a compound number.

According to studies of the Temple, the body of Mashiach is a body composed of the righteous of Yisrael. This body is a unity composed of parts. The body is composed of Yisrael and the head is Mashiach. This is the ultimate expression of ten:

A unity made of parts. According to Chazal, our Sages, the number four signifies completion, wholeness, or fullness. Thus the compound number fourteen has the meaning of its parts:

A whole or complete unity as expressed in the body of Mashiach who is the complete unity composed of member, the righteous of Yisrael.