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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.

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    \$\begingroup\$ The referenced question about requiring a check on a grapple is talking about a saving throw. It doesn't say anything about an opposed skill check, which is what a grapple is. \$\endgroup\$ – keithcurtis Nov 29 '17 at 20:22
  • \$\begingroup\$ @keithcurtis that's correct, nice catch. Doesn't change anything though. Removed the reference :) \$\endgroup\$ – Thyzer Nov 29 '17 at 20:25
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Yes

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).

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    \$\begingroup\$ Your ally doesn't need to start next to you; they can move up to you, grapple, then pull you away (provided they have enough movement). \$\endgroup\$ – Marq Nov 29 '17 at 19:40
  • \$\begingroup\$ @Marq in the example of the Giant Octopus (reach 15ft.) you would have to start your turn next to your ally (provided your base movement is 30 ft.) otherwise you wouldn't be able to pull your ally out of reach. \$\endgroup\$ – Thyzer Nov 29 '17 at 19:53
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    \$\begingroup\$ That part of your answer would be clearer if you spelled it out more clearly. For example, you don't mention anywhere that the octopus has a 15' reach. \$\endgroup\$ – Marq Nov 29 '17 at 19:59
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    \$\begingroup\$ @OganM yes you can choose to "fail" any ability check, simply by not contesting it. You tell the GM, "My character does not try to resist the grapple." and therefore there is no need for any dice rolling (you only rol the dice if the outcome is uncertain). \$\endgroup\$ – Greenstone Walker Nov 30 '17 at 5:32
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    \$\begingroup\$ @thedarkwanderer That ruling is about saving throws, not contested ability checks. \$\endgroup\$ – Marq Nov 30 '17 at 7:09
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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.

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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.

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  • \$\begingroup\$ +1 for being the only answer that addresses the role that the original grappler has in this situation. If someone has grappled Conan then just grappling Conan yourself and moving him is not going to automatically end the grapple. \$\endgroup\$ – Greenstone Walker Nov 30 '17 at 5:38
  • \$\begingroup\$ Or to phrase it another way: Grappling does not remove an already-established grapple. It just means you are grappled twice by two different characters. \$\endgroup\$ – Greenstone Walker Nov 30 '17 at 5:46
  • \$\begingroup\$ Do you have experience using this house rule? How did it work out in practice? \$\endgroup\$ – Please stop being evil Nov 30 '17 at 10:20
  • \$\begingroup\$ That's not a "house rule"; that's how the implications of the RAW work out. If you grab someone who is grappled by something else, that doesn't automatically break that other grapple and let you move the target automatically. If you magically yank the target out of the grapple, using some effect that does not have a strength rating, but simply moves the target (thunderwave, repelling blast, thorn whip, etc.) then that breaks the other grapple my moving the target out of the grapplers reach. \$\endgroup\$ – Phil Boncer Nov 30 '17 at 12:46
  • \$\begingroup\$ IOW, you can blast someone out of the mouth of a T. Rex, but to just pull him out, the T. Rex gets a chance to to have some say in the matter. \$\endgroup\$ – Phil Boncer Nov 30 '17 at 12:48

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