The following is a brief summary of some of thoughts said over by R' Frand on the parsha this evening. I have attempted to reproduce these vorts to the best of my ability. Any perceived inconsistency is the result of my efforts to transcribe the shiur and should not be attributed to R' Frand.
[As this was the first live shiur for Rabbi Frand at the Agudah in Baltimore, he began with expressing his HaKaras HaTov for returning and how happy he was to be back for the first time in 22 weeks. He had a great line where he said - "Its nice to see everyone face to face, or miktzas face to face...by the way for those of you who don't recognize me, I'm Yissachar Frand."
R' Frand said two vorts on the parsha, one of which he had said in 2018 on the mitzva of the king not having too many wives or horses and why Shlomo thought he could overcome temptation (see link here https://kosherbeers.blogspot.com/2018/08/thursdays-parsha-tidbits-parshas-shoftim.html).
The second vort related to the rules which exempt soldiers from Milchemes Rishus as described in Devarim 20:5-8. Rashi discusses a machlokes tan'aim about whether this is shelter for a person who is afraid of battles, or because he is afraid due to the sins in his closet. And in fact, the whole reason these other excuses are given is to not embarrass the person who is afraid of his sins, so that when the people leave, no one will know that the reason that he is leaving is because he is afraid of his sins.
R' Frand quotes R' Boruch Sorotzkin who asks - why are we causing such a reduction in the number of potential soldiers (by way of including battlefield exemptions for the person who has a new house, wife or vineyard), simply to avoid embarrassing the sinner? R' Sorotszkin answers that this shows how serious the issue is of embarrassing someone else and how we will go to great lengths, even to exempt 1000 other soldiers, just to prevent him embarrassment.
R' Frand added to the thought by quoting the Ramban in connection with the law that the king cannot have too many soldiers. The Ramban explains that the reason for this law is so that the king will not become overconfident based on the might of his army and think that the reason for the success is because of the army and not because Hashem is on his side. So depriving him of the extra horses will allow him to have an understanding that it comes from Hashem.
R' Frand also linked this to the story of Gidon in Sefer Shoftim wherein Hashem told him not to go into battle with 32,000 men and instead to bring 300 soldiers. This was meant to reinforce to Gidon that his victory came from Hashem.
But if this was the case there is a basic answer to R' Sorotzkin's question - it does not matter if you have all of these exemptions - because you don't need all these extra soldiers if Hashem is with you.
R' Frand closed the vort by quoting a Rashbam about the person who uses an exemption to avoid battle. He looks at himself as a shelmazel - I have no luck since I have a new vineyard and I can't even harvest it before I get pulled away. If a person looks at himself as ne'er do well and unlucky, he will not have a positive outlook on the prospects in battle. And this can translate into defeat for him as well as the others with him as morale will suffer if he thinks and publicly states that he can't succeed. So we don't send people like this into war.
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