Ambrose of Milan

The simple meaning of this is that Dan also gave a judge to Israel. For after Joshua, judges were appointed for the people from the various tribes. Indeed, Samson was also from the tribe of Dan, and he judged Israel for twenty years. But this prophecy does not signify him, but the Antichrist who will come from the tribe of Dan, a fierce judge, and a monstrous tyrant, will judge his people. Like a serpent on the road, sitting in the path, he will try to overthrow those who walk in the way of truth, desiring to supplant the truth. …

On the Blessings of the Patriarchs ↗

Jerome

And he shall judge his people, as one of the tribes of Israel. Let Dan be a serpent by the way, an adder in the path, that biteth the horse heels, so that his rider shall fall backward: thy salvation, O Lord, I will wait for. Samson was a judge in Israel, from the tribe of Dan. …

Hebrew Questions on Genesis ↗

Hippolytus of Rome

Hipp. The Lord is represented to us as a horseman; and the "heel" points us to the "last times." And His "falling" denotes His death; as it is written in the Gospel: "Behold, this (child) is set for the fall and rising again of many." We take the "robber" to be the traitor. Nor was there any other traitor to the Lord save the (Jewish) people. "Shall rob him," i.e., shall plot against him. At the heels: that refers to the help of the Lord against those who lie in wait against Him. …

Hippolytus Exegetical Fragments ↗