...Wow. Iago's thoughts on humanity are exactly what I think a Kadabra would have. I mean, look at all of the Abra that humans (most likely poachers) capture and sell at the Game Corner. I can't exactly blame Iago for wanting to enslave humanity, nor can I blame him for his world-against-me nature. From what I can tell about him (which, admittedly, isn't much), he trusts Ashley to a certain extent, and he's willing to give Pearl a chance.
I can think of only one person that fits that description: Cyrus. Apparently, in the anime, he has a legitimate job as a construction manager. In his spare time, he leads Team Galactic. He's extremely rich, and he has the same evil charisma as someone like Jim Jones, maybe more, since Cyrus used Galactic as a front for developing new energy, and nobody caught on to what he was really doing until the very end.
Yes, he's more like a machine than anything, but Cyrus has the ability to be a conman. The most important thing is knowing human nature and how to exploit it - and Cyrus can do that better than any Team leader in the Pokemon series.
While I didn't see any true errors, I would like to alert you to this sentence:
I don't know if it's grammatically-incorrect; I'm good with wild theories, off-topic rambling, and characterization, but I'm not particularly skilled at grammar and sentence structure. Still, it just sounds so awkward to read aloud. Maybe it could be slightly tweaked?
Oh, and I now have a favorite minor character: the cabbie who hates buses. I never knew your name, but you, my good sir, are my new fictional hero. I had to ride public transportation to and from school during my freshman and sophomore years; I know exactly how you feel.