The negative character of Amalek is expressed as an insensitive heart, brazenness and haughtiness.
This was the trait of the Amalekites who fought an empty war against the Israelites in the time of Moshe. The true reason for their attack was due to the greatness of the Israelites and the signs and miracles that G-d had wrought for them. Because they were conceited, they could not tolerate the reality that the Israelites were greater than themselves.
The same is true with any individual. When a person cannot accept that another is greater than themselves in the eyes of G-d or man, or that they themselves are lowly—this too is the expression of Amalek.
In order to conquer Amalek one specifically needs “Moshe’s men,” as the verse (Shemos 17:9) states: “So Moshe said…pick men for us.” The trait of Moshe is utter humility towards G-d, as expressed in Moshe’s statement in the words (Shemos 16:7), “[of] what [significance] are we?”
This humility, which is diametrically apposite the ego of Amalek, subdues and breaks the iron curtain of Amalek’s negativity.
(Torah Ohr, Shemos 83a)
