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PHB pg 195 states

Moving a Grappled Creature. When you move, you can drag or carry the grappled creature with you, but your speed is halved, unless the creature is two or more sizes smaller than you.

and the Goliath Powerful Build trait says

You count as one size larger when determining your carrying capacity and the weight you can push, drag, or lift.

So if you were enlarged VIA the Enlarge/Reduce spell, would you count as two sizes larger when grappling a Medium sized creature and thus have no movement penalty?

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No, it does not.

In particular, the Powerful Build trait says:

You count as one size larger when determining your carrying capacity and the weight you can push, drag, or lift.

It does not say anything about "creatures you are dragging or grappling."

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    \$\begingroup\$ I disagree with your interpretation. Your own quote even says "when determining your carrying capacity". \$\endgroup\$ – GreedyRadish Sep 25 '16 at 21:46
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    \$\begingroup\$ From my interpretation, "carrying capacity" relates to the inventory carrying capacity as described on p.176 of the PHB, where it says "...for each size category above medium, double the character's carrying capacity..." \$\endgroup\$ – MrNattious Sep 25 '16 at 22:18
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    \$\begingroup\$ @GreedyRadish I have the same interpretation as MrNattious. If you have a different interpretation, then go ahead and post an answer; it can only help. \$\endgroup\$ – firedraco Sep 25 '16 at 23:28
  • \$\begingroup\$ @firedraco I don't have easy access to the 5e rules, so I can't post much more than speculation. You may very well be correct, it just seems like the wording involved in this question is open to interpretation. \$\endgroup\$ – GreedyRadish Sep 26 '16 at 1:30
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    \$\begingroup\$ When the sack of potatoes you're dragging decides to try to fight back, then maybe \$\endgroup\$ – daze413 Sep 27 '16 at 5:04
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As RAW, no, it does not

Being considered a size higher for carrying capacity and push, drag, or lift force is not the same as being a size higher for all purposes, including grappling.

You count as one size larger when determining your carrying capacity and the weight you can push, drag, or lift.

As RAI, maybe

The loop hole is that the PHB has no reference on why and how the grapple-er can move without speed penalty if it is two size higher, and the DMG does not touch the subject. There are two potential scenarios for why a grapple-er one size or lower has it speed reduced, though; the grappled creature have enough leverage to make the movement difficult or that the grapple-er cannot carry comfortable enough the grappled creature as in "difficult terrain", and that the weight of the creature is the deterrent.

In the first case, since Powerful Build does not increase per-se the size, it is safe to assume that it does not help to increase the comfort or reduce the leverage and, such, the speed is halved.

In the second case, where is the weight that maters, things change. Powerful Build improves the carrying, dragging, and lift capacity, therefore the grapple-er creature does not have its speed halved.

Which one it is

The only evidence I found is in favor of is that weight is the reason for the reduction in speed. The first part is in the text of moving a grappled creature (emphasis mine).

When you move, you can drag or carry the grappled creature with you, but your speed is halved, unless the creature is two or more sizes smaller than you.

As far as I can tell, there are no rules on how you drag or, particularly, carry a grappled creature. You can carry over you head a grapple creature as if it were a sack of potatoes. In PHB 176 there is a segment that shows how can you drag, carry and lift something in particular and, as shown, it is a STR and weight contest in which Powerful Build should work as intended.

Push, Drag, or Lift. You can push, drag, or lift a weight in pounds up to twice your carrying capacity (or 30 times your Strength score).

Bottom line

At the end is the DM that has the last word. Talk to your DM and present the evidence. If you are the DM decide what it is best for your campaign. If a particular decision is more powerful that you expected it is in your right to take back the decision.

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Yes, it does

In 5e, the terms push, pull, drag, and carry are not specially defined. The closest you get is on PHB 176, where it simply describes your capacity to do these things in terms of your Strength score. Since they are not specially defined terms, we default to standard English.

Take a look at how PHB 195 describes your relation to the grapplee when moving

When you move, you can drag or carry the grappled creature with you, but <some stuff>.

With similar emphasis on verbs, the Goliath Powerful Build trait says

You count as one size larger when determining your carrying capacity and the weight you can push, drag, or lift.

Since the operative verbs here line up, I'd say that you do get the benefit of Powerful Build when attempting to move a grappled opponent.

Quick side note: it doesn't appear that Powerful Build gives you any benefit with initiating or maintaining the grapple itself, just moving during a grapple.

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