Our Parsha contains a plethora of topics and events, Para Adumah, Mei Meriva, the death of Miriam and shortly afterwards the death of Aharon, to name a few. Yet, Chazal chose a different topic from the Parsha to link to this week’s Haftara. Rather than highlight one of the aforementioned areas, this week’s Haftara, taken from Sefer Shoftim (11:1-33), tells the story of Yiftach, son of the previous Shofet, Gilaad and a zona, a prostitute (or perhaps a concubine). Scorned by his brothers due to his mother’s background, Yiftach sets out to the fringes of the desert (eretz tov) and gathers other dispossessed people (anashim reikim) around him. Yiftach is then plucked from purgatory by the leaders of the community (Ziknei Gilaad) in order to defend Am Yisrael from the king of Amon and his troops, who have come to retake the lands that Bnei Yisrael had conquered 300 years earlier as is related in our Parsha.
Yiftach, trying to deter the king of Amon from attacking, relates to the king how the land that Amon now wishes to retake from Am Yisrael was in fact conquered by Sichon, the king of Emori, prior to Am Yisrael’s appearance on the scene. The story of Sichon’s fall, which is related at the end of our Parsha, is in fact just another stage in the ongoing development of the story of Bnei Yisrael’s conquest of Eretz Yisrael, a theme which begins earlier in Parshat Chukat and will play a larger and larger role as we move through the latter half of Sefer BaMidbar. Using language which is nearly identical to the language found in our Parsha, Yiftach reminds the the king of Amon, how Sichon first took these lands from Amon to expand his kingdom, and then lost them to Am Yisrael when he refused to allow Bnei Yisrael to travel through his lands as they made their way to Eretz Yisrael. In the ensuing war he lost what he had conquered from Amon as well as his own kingdom. Amon therefore has no claim to the lands that Bnei Yisrael now inhabit. The king of Amon ignores Yiftach’s message and chooses to fight Yiftach and his rag tag army. Yiftach, in an act of true faith, or perhaps an act of true desperation, vows that if Hashem grants him salvation and victory he will sacrifice the first thing that comes to greet him after the war. Sure enough, victory is had and the king of Amon is defeated. It is this passage and the clear echoes of the events described in our Parsha, which form the link between the Haftara and our Parsha.
While that is the end of the passage chosen as our Haftara, it is hardly the end of the Yiftach story. The text continues by telling us that immediately after his victory, Yiftach is greeted by his daughter and only child. Yiftach, remembering his vow, realizes that he must sacrifice her to Hashem. Determined to fulfill his vow at any cost, after giving his daughter a two month period to prepare herself Yiftach fulfills the vow, either by actually sacrificing his daughter as a simple reading of the text suggests, or by having her live in solitude, as is suggested by several commentators.
But the tragedy of Yiftach’s life does not end there. The navi goes on to describe how the people of Ephraim, who had failed to join Yiftach’s army as they had previously promised, now come to Yiftach and ask Yiftach why he had gone to war without them. Yiftach, enraged by their insolence, goes to war against them and ruthlessly and even cruelly kills 40,000 people from Ephraim, going as far as to hunt down fugitives by means of identifying their accents and modes of speech with those of Shevet Ephraim.
The fact that Yiftach’s personality and worthiness of the role of Shofet has challenged and fascinated observers from the time of the gemara to our times demonstrates the complexities of the story we have just summarized and it’s very flawed hero. The gemara in Rosh HaShana (25B), when teaching that each generation finds itself led by the leadership it deserves, famously (and not flatteringly) compares Yiftach to Shmuel HaNavi. “Yiftach B’Doro K’Shmuel B’Doro”, Yiftach in his generation as Shmuel in his generation – this teaches us that even when the least worthy is appointed, he should be seen as the most valorous. We see that Yiftach was perhaps the least worthy of his status as Shofet, but nonetheless, he was worthy. So who was Yiftach and what made him fit or unfit for the role he is asked to play?
Even before we attempt to address these questions, it is noteworthy that Yiftach differs from all other Shoftim in that he is the only one who was “popularly” chosen by the people, as opposed to having been divinely designated. Perhaps the simplest way to understand why this happened is by looking back at Perek Yud and seeing what precipitated Yiftach’s rise to power.
Following the familiar pattern of Sefer Shoftim, Bnei Yisrael have enjoyed a relatively long period of prosperity, and as a result have once again lapsed into a form of complacency and have returned to practicing idol worship. Again, following the familiar pattern, this leads to the inevitable result of Hashem abandoning His people to persecution at the hands of the surrounding populace. And in yet another reflection of the familiar pattern, Am Yisrael turn to Hashem and pray to be saved. But now, in an unexpected plot twist, the familiar pattern fails to repeat itself, and Hashem angrily rejects their prayers and refuses to save them, instead telling them to ask their “new gods” to help them (10:11-16). Given this new and unexpected development, the people have no choice but to find a leader on their own (10:18), and they turn to the previously shunned but clearly charismatic and capable Yiftach to ask that he accept the position.
In an essay on the Haftara (M’Toch HaOhel, Haftarot, pp 357-367) Dr. Ari Mermelstein notes that we find Yiftach engaging in no less than four separate negotiations during this period. First he negotiates with Ziknei Gilaad, then with the king of Amon, then with Hashem himself and finally (at least according to the Midrash) with his daughter. It is surely not coincidental that this style repeats itself over and over. But Yiftach’s gift is to be able to apply this talent to widely divergent situations. In the first case, Yiftach is in a position of strength, he knows that Ziknei Gilaad have no choice but to acquiesce to his conditions to accept their offer of leadership, and he drives a hard bargain. When facing the king of Amon, on the other hand, Yiftach is in a position of weakness, as his subsequent vow to Hashem reveals. Yet he displays strength and confidence, ably stating his diplomatic case and in doing so encouraging his followers, sowing doubt among his enemies and successfully buying time to prepare for battle.
But as we noted, Yiftach recognizes that he is in a position of weakness, as the third set of negotiations show. Here he negotiates an agreement with Hashem himself, vowing to sacrifice the first thing that greets him should he be victorious in battle. This was a reckless commitment, as subsequent events show. Nonetheless, the audacity to try and bind Hashem to his plans is breathtaking.
The final set of negotiations are with his daughter, and they are the most heartbreaking. The Midrash Tanchuma on Parshat B’Chukotai details their discussion in great depth, but the bottom line is that Yiftach, despite his evident pain and anguish, will not be moved from his decision to fulfill his vow as he believes it must be fulfilled. All the pleas, all the arguments of how Hashem could never desire or sanction human sacrifice leave him unmoved. The suggestion that he approach Pinchas HaKohen to annul the vow is dismissed as being beneath his dignity as Shofet. The die has been cast and the decree must be fulfilled. And all of this, suggests the Midrash, is because he was not sufficiently learned in Torah (m’pnei shelo haya ben torah avbad et beato).
Based on the above, perhaps we can suggest why Yiftach was deserving of his leadership role but was also clearly deficient in many areas, to the point that Chazal viewed him as the least worthy of the Shoftim. On the one hand a charismatic leader blessed with spectacular negotiating skills and a capable military mind, whose life story gave him the wherewithal to empathise with and connect to others who were marginalized, but on the other hand hotheaded, petty and vengeful, and unwilling to bend. And most importantly, unwilling to see his own flaws and try to remedy them.
 It should be stressed that there are differing opinions regarding whether his followers were bandits or merely outcasts from a tribal society. We will follow the second approach.
 In a shiur in Yemei Iyun B’tanach (5780) Rav Yaakov Meidan suggested that Yiftach made this vow in desperation when he realized that the promised reinforcements from Anshei Ephraim were not going to appear. This would also explain the murderous animosity that Yiftach displays towards them. In this scenario Yiftach might have seen them as being directly responsible for his daughter’s death.
 The Midrash openly adopts the position quoted above that Yiftach’s daughter was in fact sacrificed.