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RBT Translation:
Judge is becoming a serpent upon the road, a stinger1370 upon the caravan-way, the One-who-bites the heels of the horse, and his rider is falling the backside.
LITV Translation:
Let Dan be a serpent on the way, a horned snake on the path that bites the horses' heels, and its rider falls backward.
ESV Translation:
Dan shall be a serpent in the way, a viper by the path, that bites the horse’s heels so that his rider falls backward.
Brenton Septuagint Translation:
And let Dan be a serpent in the way, Besetting the path, Biting the heel of the horse (And the rider shall fall backward),

Footnotes

1370

Strong’s #8207, shephiphon. This word is only found here. Traditionally thought to be a “horned viper” the root is apparently shaphaph to pierce, wound, bite. It is similar to shuph used in Gen 3:15, “he is gaping-upon [biting] the heel”