The Torah should have said, “She departed to/towards the desert of Be’er Sheva and she strayed,” for she did not stray immediately upon her entry into the desert. The sentence reads that “she departed and strayed,” implying that she did not stray only in the concrete sense: she strayed from the truth immediately upon her departure. In his commentary, Rashi suggests that Hagar shirked off the yoke of belief, exchanging it for a life of nomadic belief, straying farther and farther from the truth. We have yet to understand Rashi’s reason for saying that “straying” here does not only mean in a physical sense, but moreso from a spiritual perspective. She had alienated herself from Hashem.
Horav Sholom Shwadron, z.l., offers a penetrating response based upon an incredible incident that took place concerning the great gaon and tzadik, Horav Mordechai Pogremanski, z.l. Once Horav Pogremanski had occasion to travel by train to a distant city. It happened that he was sitting next to another traveler, a Jew who happened to be a shochet, ritual slaughterer, and mohel, ritual circumciser. The two became so engrossed in conversation that they did not realize that they had missed their stop. The shochet looked out the window and realized that they were in a strange town quite a distance from their intended destination. To make matters worse, it was Erev Shabbos and no other train was around that could take them back that day. They would have to spend Shabbos in this town far away from Jewish civilization.
The shochet was very worried: where would they find a Jewish family to host them? Where would they find kosher food for Shabbos? Rav “Mottel” told him, “Do not worry. A Jew never strays on the road. Every place that he comes to is Providential, ordained by Hashem for a purpose.” With these words in mind, they descended the train and started out into the town in search of one of their co-religionists. They quickly learned that this was a gentile town; no Jews were to be found anywhere. The shochet worried, while Horav Pogremanski maintained his conviction that they were here for a purpose, yet to be revealed.
After awhile, they discovered that there was one solitary Jew living in the town. They immediately proceeded to locate his home. When they arrived at the home of the Jew, the man who greeted them was in a state of shock. Never before had two Jews come to his door! Suddenly, the shock gave way to great emotion, as tears began streaming down the Jew’s face. After a few moments, he was able to constrain himself long enough to welcome his guests amid great joy and emotion. “What great merit I have that Avraham Avinu and Eliyahu Ha’Navi have come to grace my house,” the Jew excitedly blurted out. When they looked at him in amazement, he related the following story: “A week ago, my wife gave birth to a healthy little boy. Today is the eighth day, the day that he should have his Bris Milah. My mind has been overwhelmed with the question, ‘Who will be his mohel, who will give him a Bris?’All day I have been standing in prayer, crying out my heart to the Almighty to hear my plea. Please, Hashem, send me someone to perform the Bris Milah on my son. Undoubtedly, the two of you have been Heaven-sent for this purpose. Hashem has listened to my prayers.”
As mentioned, the shochet was also a mohel. He performed the Bris, according to halachic tradition with Rav Mottel serving as sandek, godfather, who holds the infant during the procedure. One can only begin to imagine the joy and happiness that permeated that home during that memorable occasion. As they left after Shabbos to return to their respective homes, Rav Mottel turned to his fellow traveler, commenting, “See, I told you that a Jew never goes astray on the road. It is all for a purpose.”
Horav Shwadron adds that this idea applies equally to Hagar. If she was “straying” in the desert, it is an indication that she had already alienated herself from Avraham Avinu’s monotheistic teachings, for a Jew never strays on the road. She was no longer a member of that august milieu.