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Urban Dictionary definition
2. Jack wagon
n. Slang term derived from the Freight or Chow wagons used in the late 19th century. These were often the last wagons in a wagon train, making them the least favorable to drive due to the dust, waste, and debris from the front of the train.
When used as in insult it refers to one's lack of intelligence, implying the insultee is capable of no more than operating a Chow wagon.
You're doing it wrong, you Jack wagon!
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