Arguably the most syntactically difficult among the blessings given by Yaakov to his sons before his death is his blessing to Gad: “Gad gedud yegudenu ve-hu yagud akeiv” (49:19). Yaakov here refers to two different stages – “Gad gedud yegudenu” and “hu yagud akeiv” – and likely speaks of battle, as the word “gedud” (which is used here as a play on the name of “Gad”) means “battalion,” but his precise intent is unclear.
Several classic commentators explain that this blessing foresees Gad’s prominent role in the conquest of Eretz Yisrael. The tribe of Gad – along with Reuven and half of Menashe – settled east of the Jordan River, rather than in Canaan along with the other tribes, yet it faithfully fulfilled its promise to Moshe to participate in the conquest of Canaan. According to some commentators, it is to this military effort that Yaakov here refers. Rashi explains that Yaakov prophesies that all the warriors of Gad would return home from battle peacefully, without a single one falling. “Gad gedud yegudenu” speaks of the battalions that would go out to war, and “hu yagud akeiv” refers to their triumphant return, without any soldiers lost.
In a slightly different vein, the Rashbam and Chizkuni explain that Gad would lead the Israelite army on the way to battle, fighting on the front lines, and would be the last to return from battle afterward. The first half of the verse speaks of this tribe leading the others to the battlefield, whereas the second speaks of them heading home last, as they were the most devoted and skilled warriors.
A much different approach is advanced by the Ramban, who at first explains that Yaakov here does not refer to any particular battle. The Ramban notes that the tribe of Gad settled in a large region east of the Jordan River, bordering the enemy nations of Amon and Moav, who frequently instigated hostilities against Gad. According to the Ramban, then, the first half of this verse – “Gad gedud yegudenu” – should be read to mean that armies of enemy nations would launch attacks against Gad, but “hu yagud akeiv” – Gad would respond effectively to defend its borders. Thus, Yaakov speaks not of a specific military campaign, but rather of Gad’s ongoing, successful efforts to defend its large, coveted territory.
The Ramban then proceeds to suggest the possibility that Yaakov refers specifically to the battle led by Yiftach against the nation of Amon who oppressed Benei Yisrael at that time (Shoftim 11). Yiftach was from the Trans-Jordanian region of Gilad, which bordered with Amon and thus bore the brunt of its hostilities. He was invited to lead Benei Yisrael in battle against Amon, and succeeded. The Ramban writes that Yiftach’s victory over Amon was miraculous, and it is perhaps to this great victory that Yaakov refers in this prophetic description of Gad waging battle.
It should be noted that the Ramban’s assumption that Yiftach belonged to the tribe of Gad seems difficult to understand. The Gilad region, where Yiftach lived, was settled by the tribe of Menashe, as the Torah states explicitly in Sefer Bamidbar (32:40). Indeed, Yalkut Shimoni (Shoftim, 3:42) writes that Yiftach hailed from the tribe of Menashe.
The Ramban’s comments are likely based on the verses in Sefer Devarim (3:12-13), where Moshe tells Benei Yisrael that he divided the Gilad region. Half of the Gilad mountain range was given to the tribes of Reuven and Gad, and the rest went to Menashe. Conceivably, then, the Ramban may have understood that Yiftach lived in the portion of the Gilad region assigned to the tribe of Gad, to which he belonged. (By contrast, Rashi, in Masekhet Sukka 27b, writes that he did not know to which tribe Yiftach belonged.)