LolaMoon08
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This would be just a guess on my part but it's possible that he was a drug runner and the drug dealer paid him to transport the pills up there, plus his expenses. Since we live in Texas, we've heard stories of guys making money doing this... quick weekend trip to Mexico, fast bucks, you're paid for the risks, plus they foot the bill for the trip. Needless to say it's not even a temptation but he's known guys who knew guys who did it and got away with it for awhile.
They're called "mules." The thing with Jerry, if he was ever pulled over on his way up to Maine, all he would have to do is flash his Military ID or make sure the police officer sees his Firefighter badge, and they'd have a lovely conversation about serving the community and that would be it. The Officer would let him go without even a warning because he's one of "them." A perfect "mule."