Parashat Ki-Teitzei concludes with two seemingly unrelated Commandments: using fair and honest weights and measures, and remembering Amalek's unprovoked attack against the Children of Israel. Rashi explains the juxtaposition of these two Commandments as indicating that neglect of the former leads to the event commemorated by the latter: "If you are dishonest in weights and measures, be concerned of provocation by the enemy." In other words, attacks by peoples such as Amalek come as a punishment for this sin of dishonest business conduct.


The Netziv notes a fairly obvious irony that emerges from this Rashi. The original attack by Amalek, of course, occurred in the wilderness, shortly after the Exodus. It is hardly conceivable that at this point in their history, the Israelites were already engaged in any type of commerce or trade. How, then, can Rashi contend that Amalek's offensive came in response to corruption in the commercial sphere? Furthermore, the Netziv asks, what sets this particular prohibition against inaccurate weights and measures, apart from all other forms of theft? Why does the Torah appear to single out this specific manifestation of fraud as warranting such harsh punishment?


In truth, the Netziv explains, as Rashi himself writes in his commentary to Parshat Beshalach HaShem sent Amalek against the Children of Israel for a different reason. Just before Amalek's attack, the people complained about the lack of drinking water and asked, "Is the Lord in our midst, or not?". Rashi explains that Amalek's offensive came as a punishment for this lack of faith. How can we reconcile this with Rashi’s remark in our Parsha, that Amalek punishes the people of Israel for the sin of dishonest weights and measures?


The Netziv distinguishes between classic theft and using inaccurate weights and measures in business. A person who steals on occasion does so out of greed. Swindling one's customers with dishonest weights and measures involves more than greed; it transforms one's entire financial life into a corrupt system. By including dishonesty in the standard procedures by which the individual manages his business, that person establishes corruption as an integral part, if not the defining characteristic, of his income.


This extends beyond greed; it involves a lack of faith. Resorting to dishonest practices to secure a livelihood reflects an absence of trust in HaShem’s ability to provide. Someone with a proper, honest living who occasionally cheats is plagued by greed; one whose entire livelihood works on the basis on deception lacks sufficient trust in HaShem.


Thus, we suffer the onslaught of Amalek for two reasons: for questioning HaShem’s Providence, and for indulging in fraudulent money-making practices. When we express doubt as to HaShem’s ability to provide our needs, He responds by removing His protective shield, leaving us vulnerable to the hostility of our enemies. The Torah therefore bids us to conduct ourselves honestly in business "in order that you endure long on the soil that the Lord your God is giving you".


A very pertinent message as we prepare ourselves for Rosh Hashana.


Shabbat Shalom,