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ויחלק עליהם AND HE DIVIDED HIMSELF AGAINST THEM — In accordance with its plain sense you must invert the order of the words of the verse: “And he divided himself, he and his servants, against them, at night”, as is the manner of those who pursue their enemies — they divide themselves up to follow after those of whom they are in pursuit when these flee in different directions.

AND HE DIVIDED HIMSELF, BY NIGHT. Rashi wrote: “In accordance with the plain sense of the verse it means [that they divided into groups] as is the manner of those who pursue their enemies when they flee in different directions. By night means that even after it became dark, they did not cease pursuing them.”
The correct interpretation is that he pursued the enemies to Dan during the daytime with his entire army. When it became dark and he was not able to see by which road they fled, he divided his people and servants into two or three groups, taking one part with him, and they pursued them on all roads, smiting them as far as Hobah, which is on the left hand of Damascus. Then he returned from pursuing them. The order of the words [in the verse are thus interpreted as follows]: “And he divided himself, he and his servants, by night.”

ויחלק עליהם לילה, he divided his forces all around them to make them believe that they were being attacked by large forces from several fronts. We have been told about a similar situation in Kings II 7,6 when the Aramites fled headlong after hearing noises that convinced them that they were being attacked by large forces.

ויחלק עליהם לילה, “when it was midnight, they attacked them. The word עליהם refers to the armies of the four kings, not as if it was midnight only for Avram and his men. As to the unusual expression עליהם, instead of the normative expression ויהי בחצי הלילה, “it was at midnight,” this tells us that until midnight on that night the four kings had felt absolutely safe and secure. Starting at that moment, they began to flee for their lives as soon as they found themselves under surprise attack by Avram and his men. He smote them as soon as he caught up with them, and those whom he did not catch continued fleeing all the way to Chovah, close to Damascus. The defeat was especially great, seeing that the fleeing armies left behind all their belongings, aiming only to save their lives. After having chased them such a great distance, Avram turned back and restored all the loot these kings had captured to their rightful owners.

ויחלק עליהם לילה ויכם וירדפם, “at night they spilt up and smote them and gave chase, etc.” The Midrash poses the obvious question that one does not chase after the dead, [the word ויכם being understood as “he killed them. Ed.] Therefore the word ויחלק is understood by the Midrash as meaning that the subject in the phrase is G’d, Who reserved part of this night for the miracle of the Exodus, Avraham’s descendants experiencing the killing of the firstborn Egyptians on the anniversary of that night. (Bereshit Rabbah 43,3) The plain meaning of the phrase is that Avraham and his men pursued the fleeing armies by daylight as far as Dan. Seeing that after nightfall it was impossible to see in which direction the soldiers had fled, Avraham divided his men so as to continue to pursue every escape route. He kept smiting them as far north as Chovah, a place not far west from Damascus. The Torah describes this detail so that we will realize that this pursuit continued for many days, as the distance from Chevron (Eloney Mamre) is in excess of 300 km by air. Alternatively, the entire campaign was guided by a number of miracles.

According to its plain meaning the verse should be inverted... Without inverting, the division refers to the night, and the following “he and his servants” does not convey anything. (Kitzur Mizrachi)

Es heißt nicht וַיְחַלק עליהם את עבדיו, auch nicht וַיֵחָלֵק עליהם ohne weiteres, sondern ויחלק עליהם הוא ועבדיו, und wird durch diesen Beisatz der ganz gleiche Anteil bezeichnet, den seine Begleiter an dieser Begeisterung nahmen. Nicht: er teilte seine Leute, nicht: er teilte sich, sondern: er und seine Leute teilten sich.

ויכם וירדפם, “he smote them and put them to flight.” Midrash Tanchuma asks: “who ever heard of soldiers pursuing dead people? How are we to understand this sequence in the verse?” He therefore understands our verse as meaning that Avraham and his men pursued the soldiers of that army, and G–d killed them.

ויכם וירדפם, “He defeated (killed) them and pursued them;” Rabbi Tanchum poses the rhetorical question how someone can pursue corpses? [Since the Torah first reports that these people had been smitten. Ed.] He answers that Avram killed the men whom G-d had pursued. G-d put the men to flight so that Avram could easily kill them.

לילה BY NIGHT, meaning, even after it became dark they did not give up pursuing them. According to the Midrashic explanation, it was the night that was divided): during its first half a miracle was wrought for him, and the second half was kept in reserve for the miracle of the midnight in Egypt (Genesis Rabbah 43:3).

לילה, this was also part of the subterfuge, preventing the kings from realising that they were facing insignificant numbers of opponents. In Samuel II 17,1 this was the advice to Avshalom by Achitofel when he advised to pursue David at night.

The Midrashic explanation is... [Accordingly,] “He and his servants...” is read with what follows below “ ... attacked them and pursued them.”

AND HE PURSUED THEM UNTO HOBAH, WHICH IS ON THE LEFT HAND OF DAMASCUS. It is known that there is a great distance from the oaks of Mamre in Hebron in the land of Judah, to Damascus, which is outside the Land. If so, he pursued them for many days until he forced them to leave the land for they were returning to Babylon, their country. Or possibly there occurred here a great miracle, just as our Rabbis expounded from the verse, The way with his foot he treadeth not.¹⁷²Isaiah 41:3. This is interpreted in Bereshith Rabbah (43:7) as referring to Abraham and asserting that he took such long steps that he traveled a mile without setting foot on the ground.

אשר משמאל לדמשק, “which is located to the left of Damascus,” where Eliezer and his family hailed from. Onkelos translates the word דמשק as Eliezer; he meant that Eliezer’s family in that town assisted him and Avram in that task.

עד חובה UNTO HOBAH — There is no place bearing the name Hobah, but the city Dan is called Hobah (guilty city) on account of the idolatry which would once be practised there (Midrash Tanchuma, Lech Lecha 13).

ויכם, the defeat caused them to flee.

וירדפם, the beginning of all pursuits is putting people to flight.