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In kayfabe, why would Giovanni keep bankrolling them?
(most of the time with extremely expensive machines, shit that would cost at least tens or hundreds of millions each)
despite years of constant failure?
Like I know it's a children's show and you've got to keep them as comedy jobbers to keep them likeable despite doing bad things each episode, and they'd disappear if they actually successfully caught Pikachu...but still. Can you imagine a hard nosed boss like Elon Musk signing blank cheques to a couple of jeets who piss his money away week after week with nothing to show for it for like 20 years?
The only thing I can imagine is maybe all the machines he gave them were R&D prototypes, and the purpose was IRL field testing. The real value was in the testing, the cost of the single test units was worth it.
This is backed up by the established fact that their salaries weren't high, probably minimum wage, because they were always complaining about no money and being hungry and they always had to camp out in the rough.
Either that or he regularly fucked Jessie in his office every time they came back to HQ for mission debriefing (in the ass, don't wanna deal with having to off her and keep the cops away if she got preggers and refused to abort).