The brothers grieved not only because of the precarious situation that had unfolded, but also because they could have so easily avoided this situation.  All it would have taken was a quick glance in their bags before leaving.  Realizing the opportunity they had squandered, the brothers trembled.

Parashat Miketz tells of Yosef’s harsh treatment of his brothers when they arrived in Egypt to purchase grain.  Yosef, who was the Egyptian vizier and whom his brothers did not recognize, accused them of spying and demanded that they bring their youngest brother, Binyamin, to Egypt.  Before they left to bring Binyamin, Yosef instructed his servant to fill their sacks with food and to return the money with which they had purchased it.  The Torah relates that as the brothers journeyed back to Canaan, they lodged in an inn, where one of them opened his bags.  To the brothers’ horror, he found his money in their bags.  As they were already under suspicion, they knew they would be accused of theft, and they panicked: “Their hearts left them; they trembled one to another, saying, ‘What is this that God is doing to us!’” (42:28).  (Later, when they arrived home, they discovered that all their money was in their bags.)

           

The Midrash (Bereishit Rabba 91) relates that Rabbi Levi made reference to this incident in his eulogy of Rabbi Simon.  He cried, “The tribes [Yaakov’s sons] found something, and it says, ‘Their hearts left them’; we, who lost Rabbi Simon – all the more so!”  Rabbi Levi noted that if the brothers lamented the discovery of their money, then certainly people must lament when they lose a valuable treasure, such as a great sage of Israel.

 

            This eulogy seems, at first glance, very difficult to understand.  The brothers did not lament simply because they found their money.  They lamented because the money’s appearance in their luggage would likely lead to a criminal accusation against them.  What does this have to do with the loss of a great rabbi?

 

            Rav Soloveitchik, in his eulogy for Rav Chayim Heller (transcribed in Shiurei HaRav, p. 50), explained that Rabbi Levi refers here to the angst of lost opportunities:

 

A small error of timing brought them to this anguish.  Had they opened their bags immediately after they left Egypt, they would never have been tortured by the fear of false accusation.  They could have returned the money to that queer person, to straighten things out.  But they tarried a bit in checking their sacks, and when they did, they were already far away… It would be a long way back.  To return would be difficult; to approach the strange viceroy, dangerous.  The direct way to rectify the mistake was blocked.  Therefore, their hearts went out and the trembled.  The Rabbis evaluated the reaction of the brothers to the finding of the money: “They should have checked their sacks before leaving…!”

 

The brothers grieved not only because of the precarious situation that had unfolded, but also because they could have so easily avoided this situation.  All it would have taken was a quick glance in their bags before leaving.  Realizing the opportunity they had squandered, the brothers trembled.

 

            Rabbi Levi said that he and his peers now look inside their “sacks” and find them empty, bereft of their revered colleague.  Throughout the time Rabbi Simon was among them, they had the opportunity to appreciate his qualities and stature and to draw knowledge and inspiration from his scholarship and character.  The feeling of dread and emptiness they now experience could have been avoided, if they had availed themselves of this great treasure during his lifetime.  Rabbi Levi mourned not only the loss of a revered sage, but also the lost opportunity to properly appreciate and learn from him.  His message was that we ought to appreciate and take advantage of all that we have while we have it, rather than be forced to look back later in anguish lamenting the opportunities that we squandered.