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I'm just copy pasting what I thought was an interesting article. Don't kill the messenger
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I thought it sounded like a weapon dangerous to the user. Although both that article and the Wikipedia article on the flail acknowledge that the polearm version of it did exist by way of using the agricultural flail as an improvised weapon, in some cases with military modification added.
Since part of the danger of the one-handed form is that the ball might rebound off an opponent's armor or shield, and another part is that it might hit allied soldiers, it may be that the one-handed form saw occasional use for intimidation and beating of unarmed civilians by medieval enforcers; since users for this purpose would include military personnel, the one-handed flail probably found its way into organized warfare on rare occasion (wouldn't be the first or last time somebody in a military force did something stupid), and thereby found their way into a small amount of Medieval art, but never became common due to the obvious flaws.
One thing this brings up is that Flails (at least the non-polearm variety and maybe even that variety) should be Exotic Weapons (maybe even with some additional feats required to make them good) that can be used as Martial Weapons but with the hazard of accidentally hitting your allies or yourself (the latter not for the polearm version) in case of a miss. (Same thing for the Dorn-Dergar, but at least that's already an Exotic Weapon for non-Dwarves and requires some feats for even Dwarves to make it good). Fortunately, Flails and Whips are already in the same Fighter Weapon Group.
So, the problem is the chain and uncontrollable-ness of it, right? Would a one-handed weaponized/"war" version of the agricultural flail work reasonably well as a weapon? It wouldn't seem to have any advantage for disarming and would lose the trip quality.
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Second thread, same topic!
EDIT: Link to the other one!