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I've been thinking considering Grimsely has a huge gambling addiction it doesn't seem farfetched that he's probably done a lot of things to pay those debts that come form it inevitably. Now it's not that far fetched that those things may be of a criminal nature and some of those things although not illegal may be of a unprofessional or degrading manner.
Thus it is not such a stretch that Grimisley most likely has exchanged sexual services in exchange for lots of money (mostly old men) at least several times in his life I presume. That and he has most likely gotten expelled from the Unova E4 for abusing his station in it for providing privileges exclusive to E4 to criminal organizations in return for debt removal and reduction.
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alright but he could get it tho
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Of the various leagues, two had 11 year olds as their first champions, with the first one getting another 11 year old as its second, one has a rich guy who is the son of a man who does shady shit (I'm pretty sure they implied infinity energy comes from sacrificing Pokemon en masse), one has... Ok I can't find a flaw with the Sinnoh E4 Cynthia actually knows what the fuck she's doing, one has a champion who abandoned his post for years then later gave it to a young girl who seems somewhat naive (both of which Grimsley kept his position through their leaderships), and one was run by a rich actress who didn't feel the need to stop a genocidal maniac
Somehow I think Grimsley would have no issues keeping his job
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