שְׁמַע־אַתָּ֣ה בְנִ֣י וַחֲכָ֑ם וְאַשֵּׁ֖ר בַּדֶּ֣רֶךְ לִבֶּֽךָ׃
Posłuchaj ty, synu mój, a nabierz mądrości, a skieruj serce twe na prostą drogę.
Rabbeinu Bahya
From a more psychological point of view we may understand the name as reflecting a new insight of Leah who had previously stopped conceiving after bearing four sons in short order. The word גד is related to המשכה, “continuity.” When Leah realized what was happening she decided to draw once again upon the source which had previously enabled her to bear children and by means of her prayer גד גדי, i.e. that her good fortune be restored to her she waited for additional children. When Gad was born she named him thus as he represented a vicarious continuation of her former good fortune. A similar consideration prompted her to name Zilpah’s second son אשר, the meaning of which is similar to that of Gad and also contains an element of gratitude. She hoped that her gratitude for Asher would prompt G’d to allow her to have still more children. When she personally, bore Issachar, after the story with the Dudaim, she credited the emanation בינה with her success. We read in Chronicles I 11,32 that the members of the tribe of Issachar were extremely conversant with the requirements of whatever generation they lived in, i.e. they displayed more insight than any other tribe. [This is why a delegation of 200 men from that tribe was considered as equivalent in collective wisdom to many thousands of the other tribes. Ed.] We have a verse in Proverbs 23,19 ואשר בדרך לבך, “make your heart take the proper path,” which alludes to something similar. [In modern Hebrew the verb אשר means to confirm, to acknowledge, something similar to giving thanks. Ed.] As a reward for such an attitude G’d gave her also Zevulun, a name which corresponds to the central emanation known either as קו האמצעי, or as שבט, i.e. the emanation תפארת. [According to more recent names the emanations are known as, this emanation is best translated as “harmony,” a fitting description of קו האמצעי, the “middle line.” Ed.]
Rashi
strengthen the robbed Heb. אַשְּׁרוּ חָמוֹץ. This is a Mishnaic term, אֲשַׁרְנוּהִי, “we have verified it” (Ketuboth 21a); “if I had strength (אֲיַשֵּׁר)” (Gittin 30b); “May your strength be strengthened (יִישַׁר)” (Shabbath 87a). Another explanation is: Lead him in the path of truth to acquire what rightfully belongs to him. An expression of: (Job 23:11) “My foot held its path (בֲּאֲשׁוּרוֹ)”; (Prov. 23:19) “And go (וְאַשֵׁר) in the way of your heart.”