Can you grapple-drag someone out of a grapple?

Question

You are grappled by an enemy. You cannot move (Grappled Condition), though he could move you.

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.

Now let's say an ally of yours successfully grapples you. Can this ally now use the grappling rules to move you away from the enemy that grappled you, ending its grapple?

The condition also ends if an effect removes the grappled creature from the reach of the grappler or grappling effect, such as when a creature is hurled away by the thunderwave spell.

If yes, this would mean that you wouldn't take an attack of opportunity and all it takes is one (if successful) attack from your ally, ignoring the enemy's escape DC or athletics check entirely.

Answer 1

Yes, you can

But only if you can move far enough to help the creature escape the reach of the grappler, which isn't as easy as it sounds. For a Medium creature grappled by a typical human and with a human assisting in breaking up the fight, it's no trouble. For a medium creature grappled by a Giant Octopus it's much more difficult (due to the octopus's 15 ft reach with its grapple-inflicting tentacles):

First, you have to start your turn adjacent to your grappled ally. Generally, that means you're also going to be adjacent to the giant octopus, and you'll need to be not restrained yourself. Then you need to make your grapple check v.s. the ally. Then you need to not be hit by the octopus's opportunity attack when you attempt to leave its reach; if you are, you're grappled and thus restrained and thus stop before you or your ally can exit. Your ally doesn't provoke because of forced movement, but you still do.

If you are playing on a grid, with certain specific starting positions it is possible to just barely get your ally out without provoking the attack of opportunity, which leaves you free to end your turn without the octopus getting its free attack, but that's a quite unlikely set up unless you were planning it specifically and closed with the octopus on your own terms.

And, of course, true grapple monsters like the Kraken or Roper will lose prey this way only with truly monstrous movement speeds.

Basically, this works, but is only a good idea against opponents with 5ft reach (like most humanoids, snakes, and crabs).

Answer 2

This works.

This works as described in the question, provided (as always) that the DM doesn't want to handle it differently.

It would be quite reasonable for a DM to rule that this isn't really a grapple; it's your ally helping you escape the grapple (thus: the Help action rather than the Attack action), giving you advantage on your roll to escape the grapple.

Answer 3

I'd say that if Bad Guy A has Character B grappled, and Character C grapples Character B to move him, that you now have is technically called a "tug-of-war". If Character B is unconscious, then Character C and Bad Guy A will have to contest strength with each other. If Character B is conscious, then he can Help Character C (or have Character C apply a Help action to Character B), contested by the Strength of Bad Guy A, to break the grapple of Bad Guy A, and thus enable the movement desired.

Answer 4

RAW, yes

But that isn't how I'd suggest adjudicating it.

The D&D rules help you and the other players have a good time, but the rules aren't in charge. You're the DM, and you are in charge of the game.

-- page 1, DMG, The Dungeon Master, paragraph 4 (well, technically page 4, but the first page of the DMG that isn't TOC or legalese). For the most part, I suggest sticking as close to Rules As Written (RAW) as possible, as this makes the rules predictable, and thereby fair. However, there are occasions when RAW don't make sense for every situation or outcome.

By RAW, whether or not the grappled creature was previously grappled is not considered, but logically would present more of a challenge than simply moving a willing ally who was not already grappled by another creature.

Help

The simplest (and RAW) way to adjudicate this would be to use the Help action, and grant your ally Advantage on escaping the grapple.

Escaping the grapple

If the ally was unconscious, then the conscious ally could substitute their escaping the grapple attempt for the unconscious ally to free their ally. This would not be RAW, but would present more of a challenge than simply moving the ally uncontested.

Opportunity Attacks

With a creature that has reach, if the ally was at the border of the enemy's reach, the ally could be moved relatively safely from an adjacent square. If the enemy has reach and has pulled the ally closer (a roper, for example), then you would have to risk an Opportunity Attack to move away from the enemy's reach, but not to use the Help Action or escape the grapple without moving.