Naga Sadow & Freedon Nadd vs. Jaina Solo & Ulic Qel-Droma

You literally didn't even read the entry properly. Even after the Massassi had cleared all the other Massassi out of the temples, they all knew that they collectively had very little chance of surviving an encounter with Naga Sadow himself. When he basically tore them a new one about how powerless they were without a Dark Lord to lead them, they outright began to worship the Sith like gods, just like the abominations had.

It's says they "accepted the likelihood most or all would fall to their former master. ", which is them, after just plowing through hordes of army-busting battalions, speculating that most might die in an encounter with Sadow. And Naga later implies they could've killed them, but decides to mind-f#ck with them instead and convinces them to be subservient.

Thanks for proving my point.

He outsmarts them by asking them what they would do even if they did triumph, because it'd be pretty difficult for him to construct a vast planetary network of temples to build his power without any servants. Y'know, common sense.

So your point is: Naga outsmarts Massassi that just plowed through an army, so that means he can beat them? Kewl.

Except you're ignoring that those very Massassi, due to their ambitions for power, freely went in knowing that all would likely die in the attempt.

They accepted that it was probable that most of them might fall before Sadow, but we don't even know how. It might be due to his skill as a warrior, power in the Force, a ritual he can perform to Drain them, etc.

That the Codex itself (which is supposed to be an objective source) noted that the Massassi accepted that they would likely fall to Sadow makes a solid case for him. Also, I believe the attack was too immediate for Sadow to prepare an elaborate ritual, so chances are that it refers to combative prowess, whether related to his Force abilities or prowess with a blade.

The Massassi just fought through several army-busting battalions, and then accepted the probability that if they fight Sadow they will fall. Also, there's the possibility they were referring to Naga and his forces, not just Naga himself.

They killed all the other Massassi, as the codex explains.

Not when they drew the conclusion that most of them falling before Naga is a probability.

They said that it was a likely event.

They accepted the likelihood of most, maybe all, of them falling before Naga(and his forces, potentially). Not only is this already only a probability, they say most as if some may survive and Naga might die, then say maybe all opening Sadow's chances to victory. And it's unclear if this is Naga Sadow himself, or Sadow and his forces. So it's not 100% certain Sadow can fight and kill them all, and is ultimately damn vague.