On his deathbed, Yaakov gives blessings to all his children. The first three sons — Reuven, Shimon and Levi — receive farewell wishes which are not as pleasant as those given to the rest of their brothers. The remaining blessings are shrouded in depth, meaning, and a sense of prophesy. It seems that Yaakov is talking to each tribe in their present, sometimes referencing their past, but also speaking to future generations and events.
Some commentaries go into great detail to try to explain these blessings, while others lay off, as the interpretation of the blessings is a bit overwhelming.
The blessing given to Naftali is one of the shorter ones, only six words (Gad also has six, and Asher has seven words), but it is probably one of the more misunderstood blessings.
The common translation suggests Naftali is comparable to a hind — “Naftali is a deer running free; he delivers words of beauty.”
But, as Rabbi Aryeh Kaplan notes in his Chumash, each word has other possible meanings. The word ayalah “can also be translated as a tree or plain.” Of course, once we are possibly talking about an intangible object, such as a piece of land or a tree, the phrase translated as “running free” will have to be retranslated as well.”
This is why he offers the other translations of “Naphtali is a spreading tree, that puts out beautiful branches,” quoting the Baalei Tosafot and the Malbim, and “Naphtali is a full-bearing field, that bears beautiful trees,” following the view of Chizkuni, HaKtav V’Hakabbalah.
The Rav Peninim Chumash has an entry explaining the blessing of Naftali. We need to see the Hebrew words to understand: Naftali ayalah shluchah hanoten imrei shafer.
Ayalah – comes from the word Ilan, which means a tree, as per the verse in Isaiah 1:29 in which “Eilim” reference trees.
Shluchah – comes from a word which means to spread out, such as in Yechezkel 17:6, when the verb is used to mean “sent forth boughs,” or Tehillim 80:12, “It sent forth its branches to the sea.”
Hanoten – means to give
Imrei – means branches, like in the verses in Isaiah 17:6,9 in which the word amir appears.