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We know, thanks to the DMG, that a creature has disadvantage with a weapon sized larger than itself, but the wording is less clear concerning the damage. My reading is that the increased damage is considered (mechanically at least) to be due to the weapon being oversized, rather than the wielder, but I would like some second opinions. (RAW and RAI interpretations both welcome)

So, would a medium sized creature, specifically a Monk PC, wielding an oversized (large) spear deal 2d6 damage on a successful hit? Furthermore, would a large creature with a huge spear deal 3d6? Etc, etc, etc.

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Technically speaking, yes. The looted weapon will still deal extra damage.

Big monsters typically wield oversized weapons that deal extra dice of damage on a hit.

The "that" is pretty clear - the weapons deal extra damage, not the monster.

However, you should be extremely cautious in making these rules (and weapons) accessible to players. The rules on creature size are in the PHB, but these rules are in the DMG. They're not meant to be easily accessible to players.

A player who is making a conscious effort to gain advantage on their attacks can do so fairly easily. That makes wielding oversized weapons a pretty nice option for any player who wants to build around it. At the very least, if you're planning to allow this, consider implementing the suggested rule that it is impossible to use a weapon two sizes too big.

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    \$\begingroup\$ The disadvantage on attacks more than compensates most of the time for the increased base damage if you do the math. I would allow it until the player finds out he traded for the worse. \$\endgroup\$ – András Apr 3 '16 at 10:25
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    \$\begingroup\$ @András Only if they're actually taking disadvantage on their attacks. A player who builds around this could easily cancel it out by giving themselves advantage on all their attacks. \$\endgroup\$ – Miniman Apr 3 '16 at 11:27
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    \$\begingroup\$ Actually, having advantage with a normal weapon is stronger (GWM, static bonuses) than a attacking without advantage with an oversized weapon \$\endgroup\$ – András Apr 3 '16 at 14:11
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    \$\begingroup\$ The bigger issue would be if they already have disadvantage - another source of disadvantage has no further effect. So a monk could use unarmed attacks most of the time, using the large spear only when disadvantaged, for example. \$\endgroup\$ – Paul Hutton Apr 4 '16 at 6:28
  • \$\begingroup\$ I would like to add that PC classes are not necessarily proficient with the variant weapons of large and larger monsters as well. This would mean they don't get their proficiency bonus as well as have disadvantage until they spent a good amount of time overcoming that, rules are in the DMG for that as well. The PHB just says they are proficient in the list there. Monsters have different rules as many are fond of quoting so their weapons are not technically on the list in the PHB. \$\endgroup\$ – Slagmoth Feb 19 '18 at 20:58
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Yes. The same rule applies to Small creatures wielding heavy weapons. So I think that your logic is sound.

PHB, page 147:

Heavy. Small creatures have disadvantage on attack rolls with heavy weapons. A heavy weapon's size and bulk make it too large for a Small creature to use effectively.

There is no reduction in the damage dealt when a halfling uses a great sword (for example), so I don't see why your medium sized monk should do any less damage just because the weapon is oversized for him/her.

However, I'd expect that if the monk was also a Small creature, that he wouldn't be able to use the weapon at all.

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