Can multiple creatures grapple a single target?

Question

I'm creating a druid and came across an interesting tactic that seems to be both overpowered and allowed as the rules are written. (Our characters will be level 5 due to people wanting to keep their previous characters from our last campaign.)

The scenario is this:

• The party comes across a scary enemy.
• The druid gets the highest initiative.
• Druid casts "Conjure Animals" as a third level spell.
• He decides he wants 8 Constrictor Snakes (or any other sized beasts that can grapple) to surround the enemy.
• The initiative roll for the group of snakes allows them to act next.
• The druid commands them to attack the target. (They obey any verbal commands that you issue to them, no action required.)
• They all attack the target and grapple him. (Based on their action "constrict". Basically if they hit they deal damage and automatically grapple.)

This poses several questions:

• Can multiple creatures grapple a single target?
• Would this require multiple attempts to break free?
• How would you deal with different creatures with different "break free from grapple" saves?
• How would this apply to different beasts? (Constrictor Snakes, Crocodiles, Giant Crabs, Giant Octopi...)

Answer 1

A creature can be grappled by multiple creatures, and it has to make a separate escape attempt against each one.

Grappled

• A grappled creature’s speed becomes 0, and it can’t benefit from any bonus to its speed.

• The condition ends if the grappler is incapacitated (see the condition).

• 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.

There's nothing in the Grappled condition that would prevent multiple creatures from grappling a single target.

Where it gets complicated, though, is breaking free. From the grapple rules for monsters, we have this:

A creature grappled by the monster can use its action to try to escape. To do so, it must succeed on a Strength (Athletics) or Dexterity (Acrobatics) check against the escape DC in the monster’s stat block. If no escape DC is given, assume the DC is 10 + the monster’s Strength (Athletics) modifier.

This says that the creature must succeed on a check against the escape DC in the monster's stat block. That indicates that it's talking about a single escape DC, a single monster, and therefore, a single escape attempt.

So, this makes it clear how to deal with different creatures with different escape DCs - the grappled creature has to make a separate escape attempt for each one.

All the creatures you've listed have grapples that work exactly the same way, just with slightly different numbers. So, as above, the grappled creature would have to make a separate escape attempt against each escape DC.

This is a fairly powerful tactic at low levels, but against stronger creatures the initial grapples are unlikely to succeed, and higher level enemies often have ways of dealing with grapplers (like teleporting out, or just killing them all at once). It's also important to remember that you can't grapple a creature more than one size category larger than yourself, so your snakes will never be able to grapple a tarrasque (for example).

With all that said, if this tactic is becoming a problem, the DM might consider allowing a monster to burst out of multiple grapples at once, especially if it's clearly strong enough to do so.

Answer 2

If two or more opponents are both grappling the character separately, then the character would need to roll separately to break each grapple. Each is a normal ability check which is an action, so they'd be limited to however many they can do in a turn, normally one.

In this case however you might just model this as the second guard using the Help action, which would provide the first guard advantage. This would allow for a one-round breakout.