I know this might not sound like a legit answer or the comparison I'm making will not make sense either but hear me out. I know in the world of Pokemon most of the people you are likely to encounter are adults working "real jobs" for the most part having outgrown Pokemon and have decided to work with most of them sometimes keeping their Pokemon around almost like house pets if you will. For example, from Battle Frontier the coordinator May fought with the Butterfree/Venasaur named Jeremy. An adult who used to be in a band before having an office job and family and before that he was known for being a powerful trainer.

Other than "normal adults" I know there are a lot of them who still raise Pokemon but most of them are in high ranking positions like Gym Leader, E4 or work "normal" jobs like medicine, doctors, construction but they all in some aspects involve Pokemon; Pokemon medicine, using Machop to lift heavy items in construction, etc. The other group which seems to be the largest is of course; young Pokemon trainers!

Now, with TR's mission being to steal powerful Pokemon which group of people typically has Pokemon "easier" to catch? To me the answer would be "children" by that I mean new trainers who happen to be 10-years-old.

Remember the movie Home Alone? I'm talking about the original one. We have two "bumbling" crooks (sound familiar doesn't it) robbing house after house on Christmas Eve when the families go out of town and with Harry being the competent one it seems their plan was actually a good one; he dressed as a police officer (costume, sounds like TR doesn't it?) going inside every house wanting information on how long the folks would be out of town, when they left, if anyone else would be home, what time the Christmas lights would come on, etc. This literally gave him a free pass inside of EVERY house to see everything to see which ones in the neighborhood have items in it worth stealing.

Everything is going well...except...when they get to the house with Kevin (he's 8 not 10 but hey close enough right?) and here they find their greatest competition and ultimately fail twice if you count their second encounter. Irony of it is that unlike TR who usually fall into their own traps mainly pitfall ones, the crooks in this movie fall for the child's.

Something tells me that TRio PROBABLY didn't have many missions/jobs working for TR that involved children. Don't get me wrong they were probably sent out to be steal items. In all honesty, BEFORE like Hoenn and DP when they were truly changed in personality in some aspects such as Jessie's desire to be an actress and whatnot screwing up their operations such as one where she poses in front of a camera when they were escaping out of some warehouse after stealing items to build a machine. I think it was the episode where Dawn catches Buneary.

My point? Believe or not I think TRio is actually a competent group of crooks BUT only when they steal items. To me it is when they decide to add Pokemon to that list of "items" they somehow screw it up almost EVERY TIME; usually through Jessie's greediness or Meowth's overconfidence especially in terms of the tech that he supplies for the group like an attack-resistant net or usually the electric-proof equipment they use. James is to me the "neutral" one being that I think he is the least "evil" or as evil as you would consider them to be (I don't think James is greedy put it that way Jessie and Meowth are which makes sense the both of them didn't come from a rich background like James did) with him simply going along with the plans and whenever he is the one to put a plan together (which is a rare occurrence) ever notice how the team ALMOST gets away with their plans?

Anyway, something tells me that their early missions that were successful ones involved stealing a person's possessions rather than Pokemon. It was only when they were sent on specific jobs to get Pokemon (A.K.A.; their first encounter with Ash which happened by chance) that is when things went downhill.

Think about this; where is TR Headquarters (well I seriously don't know because in the games and anime that term "Headquarters" is used lightly since it changes after each defeat of the leaders of TR as the journey goes on) let's just say Viridian City!

The Pokemon Center is like right there near the gym (were Giovanni is "headquartered" with TR) and why not rob it until now? Seems to me that Pokemon Center was probably not for any ordinary TR Grunt it is probably for more "experienced" agents in the organization and before they broke in; we've already agreed that the TRio had made a name for themselves in Kanto mainly due to the wanted posters being evidence of that so I'm sure the "boss" assigned that job to them I don't think it was a stunt they pulled just to pull.

Think about it; if they f'ed up (which they did but seriously they were up against a "army" of electric rodents that ended up blowing the center to pieces thanks in part of Koffing's gas) wouldn't there be some sort of investigation city wide possible leading the cops...I mean "Jenny's" to the gym uncovering TR? POSSIBLY but I'm sure the TRio thought ahead (surprisingly) if this was the case. I mean again my strongest piece of evidence to support that theory is that why wait that long before robbing a center full of Pokemon that has been there a long time right across from the gym (at least I think its that close?)

Going even further the Pokemon Center might have been the first operation (or one of the first) where the TRio pursued Pokemon as the target. Think about their entrance exam; it was to steal a statue I think???

They were probably sent out after other items of value and as they climbed the ladder of their mission they eventually got to the point where they were assigned missions to steal Pokemon. Kind of explains why the only Pokemon they have is Meowth (in the test). In one episode, they mentioned getting their Pokemon as a birthday present/Christmas gift (Island of the Giant Pokemon) possibly hinting that for awhile after passing their exam the only Pokemon in their group was Meowth.

What do you think?

I know, I know I seem to ramble on most of the time but I think this "theory" of mine actually has some value to it...you know if you read the whole thing to consider it xD

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