I've GM'd a local Sheriff in a southern county who 'grew' almost unwillingly into a warlord as other elements including the state and local elected officials proved incapable of providing order and/or security. His intention was to protect his county and ensure justice. This certainly has historic precedence.
As does the wealthy cattle baron, minor or farmer hiring protection that eventually grows into a 'militia' of its own. This scenario has occurred in Columbia where "FARC" guerrilla (originally a Marxist group) have basically become the security force for drug growers, who have then grown to control significant portions of real estate, has occurred in recent history.
In many cases the difference between a militia band, a contract security force and a warlords army might be almost semantic. In all cases, the truth will be colored by the intent, beliefs, perceptions and propaganda of the various speakers.
If he is my enemy, I might call a a charismatic and effective leader of a county militia, a warlord, gang leader, or warcriminal... Of course if he's in my pay or doing my bidding he's a brave defender of the helpless. If I'm a single mother who is being protected, I might call him a hero or even willingly 'my lord' and be proud of his successes.
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