The cryptic phrase “brood of vipers” (γεννήματα ἐχιδνῶν), in Matthew 3:7; 12:34; 23:33 and Luke 3:7, stands out as a shocking rebuke by both John the Baptizer and Jesus of the religious leaders of their day. This metaphor, portraying them as the offspring of venomous snakes, certainly points to their evil spiritual nature. When this epithet appears, it highlights the inherent unrighteousness of these leaders and, consequently, is often accompanied by warnings of impending judgment. However, does this phrase simply point to their evil nature? Grappling with this question, scholars have sensed that there may be more to this epithet. Some suggest that John uses this in collocation with the fire of judgment to evoke imagery of snakes wriggling away from a fire (France, 2007). Others argue that the epithet speaks of danger, perhaps alluding to the danger Jesus will face at the hands of these leaders (Blomberg, 1992; Hendriksen, 1982). Several have suggested a connection to Satan as his offspring with Gen. 3:15 in view (Perrin, 2022, Davies and Allison, 1988, Blomberg, 1992), although they stumble against the use of the plural “vipers,” which seems to militate against this theory (Davies and Allison, 1988). In a thorough study of this phrase by Keener, he suggests that this denunciation is related to parent murder, highlighting the tendency for the offspring of snakes to murder their parents (Keener, 2005). However, this suggestion does not gain adequate support in the relevant contexts. In another article, Knowles argues for wordplay on the Hebrew terms for serpent, scribe, and Pharisee (Knowles, 2014), although this too seems to be a stretch. In this paper, I will affirm the evil connotations and connection to Satan and Gen. 3:15 in this epithet but propose that the plural “vipers” does not speak directly of Satan himself but of those in the evil seedline descended spiritually from him who have persecuted God’s servants and prophets throughout time. Elucidated especially in Matthew’s Gospel, although carried over into Luke’s, these leaders are placed directly into this line of violent persecutors seen vividly throughout the OT and alluded to in the Gospels themselves. Furthermore, this epithet highlights their future persecution of the elect: John, Jesus and his followers. As such, Jesus also points to their judgment for this bloodshed while denying their inclusion in the elect family and their right to inherit the kingdom.