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I recall in Johto, they had a huuuge money debt because they kept borrowing from the organization.
Anyway, they get their money by having a lot of part time jobs and what not. Frequently, we see them doing things like running stalls and such to make money.
It's been said a couple of times in the anime, although I cannot recall which episodes exactly, that the TR HQ people or Giovanni chain them money. Like one poster above me typed, there was that episode in Johto about the debt. I don't think the main TR "head Honchkrows" have given up on Jessie, James, or Meowth.
In one of the 1st Sinnoh episodes, they called Giovanni from James' parent's vacation home. He said they didn't have a TR Sinnoh department (or something along those lines) so they could start one. And a reminder could have been when Jessie sent the Yanma to Giovanni, which he later sent back.
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