My answer was simple: we're not trying to "win" - at least not by the standard definition.
After all, it seems like we - Israel and Hamas - are playing a very different game. They're trying to kill as many of us as they can, and we're trying to kill as few of them as we can. How do you define "winning" and "losing" when the two sides are playing with different rules? How do you fight a war when you're trying specifically not to kill people.
And yet, we're not the first Israelis who had an aversion to fighting. Actually, the first Israeli to demonstrate such an aversion was Yisrael - Ya'akov himself.
As he returns from Haran towards Canaan, Ya'akov sends a message of peace to Eisav, hoping to avoid a confrontation. Yet, when he learns that Eisav too approached, with 400 armed men, we read that, ויירא יעקב מאד ויצר לו - "and Yaakov was greatly afraid, and he was distressed." Essentially he was frightened twice. What's the difference between ויירא - "he was afraid" and ויצר - "he was distressed"? Rashi explains,
Ya'akov wants to have his cake and eat it too. He'll fight if he has to, to protect his family. But he's particularly disturbed about the prospect of having to kill others, no matter the justification.ויירא שמא יהרג, ויצר לו אם יהרוג הוא את אחריםHe was afraid of being killed, and he was distressed that he might kill others.
That's the way of the Jewish people. We'll fight if need be, to defend ourselves. But there's no thirst for blood, and whenever possible, we will try and protect the even the lives of those who despise us and wish us ill will. Ya'akov was distressed not just about the possible deaths of innocents; rather, he worried about having to kill anyone - even among Eisav's four hundred warriors.
The fact that we didn't "win", I told my son, isn't a weakness. If anything, it's a source of strenght, and a badge of pride worn proudly by the soldiers of Israel. I go to sleep well at night knowing that, if need be, our soldiers will do what they must to protect us. But, first and foremost, whenever possible,
דרכיה דרכי נעם וכל נתיבותיה שלום - "Her ways [of the Torah] are ways of pleasantness, and all of her path are peace."