(All thanks and praises to Lectorel, who came up with the original idea for this).
The Jedi have no idea how many discarded Initiates and would-be padawans have actually fled the Service Corps. The Agricorps. The MedCorps, the EducCorps, the ExplorCorps - it’s a silent, but by no means hidden truth that a large percentage of their members simply - vanish. Missing, presumed dead is the official designation - after all, they are where they are by the will of the Force, and what Jedi - Knight or not - would ever go against that?
The Jedi, however, are entirely ignorant of how many of those disappointed, embittered former Corps Members go Dark.
They know how to keep their heads down. Most of the darksiders Obi-Wan encountered as a teenager were spice addicts and alcoholics, using the Force to clean out casinos and win at gambling. The more successful ones worked for the Cartels - but their ambitions (or lack thereof) were no indication of their abilities.
He learned more about pain then he has in his entire life - before or after - from a crippled Twi’lek who worked the gambling houses. A human employed at a dingy brothel taught him how to twist and shred memories with a fineness that nearly drove him insane. And desire - that, oddly enough, he learned from a part-time beggar who instructed him on the razor-thin edge between want and need.
They’re a network - unofficial, unremarked, but still present - stretching across the galaxy like the faintest of black spiderwebs.
Obi-Wan Kenobi is a Dark Lord of the Sith. He doesn’t particularly want an army - he’s more then content there days with training his student and watching over the small group of people who have claimed him as family. Even so.
If he wanted an army, he could have one.