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What does the term jack wagon mean?

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Jack wagon is a derogatory term for a gay person.

A “Jack Wagon” was simply a large wagon that hauled the large manual jacks used back when logging was done by hand. The trees were raised slightly by these jacks to allow cutting into more managable sizes for transport from remote forest locations. Over time, with the introduction modern mechanized equipment (e.g. large “Bobcat”-type vehicles, etc), the need for these heavy hand cranked jacks disappeared. Spotting a “Jack Wagon” at a logging site came to mean you had found a crew that was seriously behind the times and out of touch with gettin the job done.
“When WWII broke out and logging camps were cleared out by the draft, this term was applied by these former loggers / new recruits to the seriously out-dated equipment the US military entered the war with. Many units were initially fielded with WWI-era rifles and artillery. The term “jackwagon” (reduced to one word) found a quick home with these troops and spread to become a general term for anything out-dated or out-of-touch with surrounding reality.
   When cursing and swearing at recruits was banned in the post-Viet Nam era U.S. military, drill instructors (DI’s) had to find a new vocabulary to get their very loud message across. And one of the terms appropriated was “jackwagon”, meaning a recruit who was not focused on reality, the here and now or the requirements of the job at hand. The term as originally construed had little to do with insulting homosexuals despite the fact that anyone who's sexual compass is skewed to the evolutionary dead-end of same-sex activity certainly fits the descriptive nuances of the expression....

Jackwagon: 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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