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If a Water Elemental were to use the grappling rules to grapple a Huge creature (since it is Large), would that creature then take damage from this:

At the start of each of the elemental's turns, each target grappled by it takes 13 (2d8 + 4) bludgeoning damage.

Or does this damage only work against the one Large or two Medium- creatures that get stuck by Whelm?

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The Elemental can not use the grappling features of Whelm on a Huge target

The Water Elemental(Basic Rules, 158) stat blocks states with my empahsis:

Each creature in the elemental's space must make a DC 15 Strength saving throw. On a failure, a target takes 13 (2d8 + 4) bludgeoning damage. If it is Large or smaller, it is also grappled (escape DC 14). Until this grapple ends, the target is restrained and unable to breathe unless it can breathe water. If the saving throw is successful, the target is pushed out of the elemental's space.

The elemental can grapple one Large creature or up to two Medium or smaller creatures at one time. At the start of each of the elemental's turns, each target grappled by it takes 13 (2d8 + 4) bludgeoning damage. A creature within 5 feet of the elemental can pull a creature or object out of it by taking an action to make a DC 14 Strength check and succeeding.

There is no option for grappling a Huge, just that if it is large or smaller it is grappled. Huge and Gargantuan creatures are not valid targets for this grappling effect and subsequent damage. And the 2nd paragraph of the Whelm action still contains the requirements on size.

Grappling outside of Whelm

While there are rules around grappling creatures one size larger, those rules don't apply to Whelm's actions. Only the requirements within the Whelm action are relevant to determining how the Whelm works.

Meaning that even if they could grapple a Huge creature (which may be up to a DM to determine), they can not Whelm it.

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    \$\begingroup\$ So are you saying the Huge creature would be underwhelmed? \$\endgroup\$ Commented Oct 29, 2020 at 18:05
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No

The extra damage is contingent on the Whelm action, not the grapple attack. Huge creatures are not a valid grappling target for Whelm.

If you were to interpret the damage as applying to any grappled creature, you would also have to include this line:

The elemental can grapple one Large creature or up to two Medium or smaller creatures at one time.

...which would prevent grappling Huge creatures anyway.

Does it have hands?

Remember that the grapple attack requires a free hand, which the water elemental may lack:

Using at least one free hand, you try to seize the target by making a grapple check instead of an attack roll

It is not explicit from the description whether water elementals have hands or not, but if a GM rules they don't then the grapple special attack is unavailable to them.

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  • \$\begingroup\$ I'm not sure the lack of hands on the creature prevents grappling, when they specifically can grapple (certain sizes) of creatures. \$\endgroup\$
    – NotArch
    Commented Oct 29, 2020 at 17:44
  • \$\begingroup\$ It doesn't prevent grappling; just the grapple special attack from the Player's Handbook \$\endgroup\$ Commented Oct 29, 2020 at 17:48
  • \$\begingroup\$ Are we assuming then that water elementals can't have variable forms that may include grasping appendages? \$\endgroup\$ Commented Oct 29, 2020 at 18:17
  • \$\begingroup\$ Side note: I can't find the official art for them to definitively say they absolutely do or don't have hands anyways. \$\endgroup\$ Commented Oct 29, 2020 at 18:22
  • \$\begingroup\$ @RevenantBacon Official art has some appendages, but hands are unclear. \$\endgroup\$
    – NotArch
    Commented Oct 29, 2020 at 18:31

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