The Torah devotes a lengthy section in Parashat Toledot to the story of Yitzchak’s experiences living among the Pelishtim in the southern Israeli region of Gerar (chapter 26). His difficult and complex relationship with the hostile and envious Pelishtim ended peacefully, when he and Avimelekh, the Philistine ruler, made a formal truce.

There are several similarities between Yitzchak’s meeting with Avimelekh, and the agreement reached by his father with the same ruler (or perhaps Avimelekh’s predecessor with the same name) years earlier. In both instances, Avimelekh approached the patriarch to initiate a peace treaty, acknowledging that the patriarch has been the beneficiary of divine grace (Avraham – 21:22; Yitzchak – 26:28). Avraham, in his talks with Avimelekh, protested the theft of water by the king’s servants (21:25), and Yitzchak, similarly, spoke critically to the Philistine ruler about the abuse he suffered at their hands (“You despised me, and sent me away from you” –26:27). Finally, both episodes end with the naming of the site “Be’er Sheva” (21:31, 26:33).

However, as Rav Amnon Bazak noted, there is a significant difference between the two meetings, which points to a basic difference in the way the two patriarchs handled the diplomatic situation that they confronted. When Avimelekh approached Avraham and expressed his interest in making a formal treaty, Avraham immediately gave his consent (“Anokhi ishavei’a” – 21:24). Only thereafter did Avraham then present his complaints about the Philistines’ theft of his water. Yitzchak, by contrast, submitted his protest immediately upon Avimelekh’s arrival, indicating that he would not consent to a formal agreement unconditionally. Furthermore, a careful reading of the two narratives reveals an important difference between the natures of the two agreements. Avraham, after voluntarily giving sheep and cattle to his adversary as a kind of proof to his ownership over the disputed well, establishes a berit (“covenant”) with Avimelekh. Even though Avimelekh requested only an oath confirming the end of hostilities (21:23), Avraham offers something more that –a formal alliance. In Yitzchak’s case, just the opposite occurs. Avimelekh asks for a berit (26:28), but in the end, they simply make oaths to one another (26:31).

The Sages of the Midrash (Bereishit Rabba 54:4) were critical of Avraham’s handling of the situation with Avimelekh:

The Almighty said to him [Avraham]: You gave seven sheep without My consent… I swear that, correspondingly, they [the Pelishtim] will kill seven righteous people from among your descendants… Correspondingly, his [Avimelekh’s] descendants will destroy seven sanctuaries of your descendants… Correspondingly, My ark will spend seven month sin a Philistine field…”

It appears that the Sages preferred the guarded, suspicious approach taken by Yitzchak over Avraham’s overly magnanimous and trusting response to the Pelishtim. While Avraham generally emerges as a sharp, confident, clued-in public figure, whereas Yitzchak strikes us as more private, introverted and less competent in the public arena, in this instance, Yitzchak’s approach proved more successful than his father’s. Indeed, Avraham’s berit with Avimelekh was short-lived, and the Pelishtim stuffed his wells soon after his death(26:15). By contrast, we do not find the Pelishtim initiating hostilities against the patriarchs at any point after Yitzchak’s cautious truce with Avimelekh. Chazal thus concluded the Avraham acted wrongly in granting his unconditional forgiveness to the Pelishtim and making an alliance with them on such generous terms. As the Torah goes to great lengths to emphasize later, in Parashat Vayetze, in describing Yaakov’s experiences with Lavan, we must proceed with caution, and even cunning, when dealing with dishonest, unscrupulous people. The Sages therefore approved of the guarded, careful approach of Yitzchak, and criticized the overly benevolent gestures of Avraham.