and then they proceeded to be the worst at their jobs for the next 20 years

No no, you don’t get it. Jesse and James are the absolute best there is at their jobs, but they have no idea what their jobs are.

They think that they’re thieves, agents of an elite criminal group led by Giovanni, stealing rare pokemon and advanced technology and such. And there might have been a time this actually was their jobs. In the first season or two, they frequently get angry phone calls about how they’ve fucked everything up, or get their expense account cut off because they have literally never turned a profit on their criminal enterprises and constantly procure and then lose/destroy expensive and elaborate devices.

But then the world came within a hair’s breadth of being destroyed, several times, and Jesse, James, and their weird cat rescued everybody. As terrible as they’ve always been at criminal endeavors of any kind, when the apocalypse approaches and they’re forced to step up, they’re really fucking good at saving the day.

And Giovanni is over here like… if the planet is destroyed, or time/space becomes unrecognizable, or civilization collapses, there’s no way for me to run a profitable criminal enterprise anymore. I need this planet, because it’s where I keep all my stuff. And I don’t pretend to understand the why of it, but these couple of bumbling nutcases that I should have fired years ago seem to be an important component of that? Somehow? So you gotta stop thinking about them in terms of acquisitions and start considering them… loss prevention. As in, even if you waste a million dollars a month on giant cat-faced robots and a vast array of fancy ball gowns and they never turn a profit, they are preventing all of your assets from going away at the same time because of something you can’t do anything about.

And that’s the great secret behind Team Rocket. These guys aren’t thieves, they’re professional superheroes (sponsored by organized crime). Of course, nobody ever bothered to tell them that.

“To protect the world from devastation…”

Plus, as is frequently pointed out: Jesse and James are good at every other job EXCEPT Team Rocket. They’re actually smart businesspeople and run successful food and merchandise stands and are great salespeople.

Hell, even in Team Rocket situations where they’re not chasing after Pikachu they’ve done better.

It’s just their Achilles Heel is one damn OP rodent.

Pikachu Proximity Intelligence Chart