Can a grappler grapple the same target multiple times?

Question

The PHB states:

Using at least one free hand, you try to seize the target by making a grapple check

But if the grappler has another free hand, can he grapple the same target again, with the other hand?

More importantly, if this is all possible, and the character successfully grapples the target with multiple limbs, does that mean the target will have to use an action, and succeed, for each grapple, to break free?

The idea is that a strong grappler can maximize the probability of keeping a target grappled by using more limbs. And a grappler with many limbs, can increase those odds even more.

Answer 1

By RAW, probably.

Here's the relevant rule (PHB, p. 290):

If multiple effects impose the same condition on a creature, each instance of the condition has its own duration, but the condition’s effects don't get worse. A creature either has a condition or doesn’t.

For example, if a creature had the paralyzed condition from both a hold person spell and from the effect of a ghoul's attack, saving against the hold person effect wouldn't end the paralyzed condition until the ghoul's effect was also saved against.

So as long as your DM agrees that your two grapples are separate 'effects', there's nothing in the rules that seems to prevent you grappling the same creature twice. The creature would need to break each grapple separately (per the rules on PHB. 195 for "Escaping a grapple").

However ...

Your DM might quite reasonably rule that, absent other rules, a grappling character (rather than a grappling limb of a character) constitutes a single 'effect' for the purpose of imposing the grappled condition. If so, then you can only impose one grapple on a given creature.

Answer 2

On the same turn, no.

PHB pg. 195

When you want to grab a creature or wrestle with it, you can use the Attack action to make a special melee attack, a grapple.

You make the Grapple attack in place of your regular attack, thus you only get the one attempt, regardless of how many hands you have free.

An Extra Attack feature gives you the opportunity to Grapple the creature again, however, should the first attempt fail.

PHB p. 195 again

If you’re able to make multiple attacks with the Attack action, this attack replaces one of them.

A creature is either Grappled by you or it isn't.

PHB p. 290: "A creature either has a condition or doesn’t."

Much like advantage/disadvantage, the condition doesn't stack.

Answer 3

Rather than multiple separate grappling attacks, and multiple grapples in effect, I would rule that one creature grappling another has one grapple in effect. Grappling requires a minimum of one free hand, so if the grappler is using both hands, maybe the DM gives him a +2 on his contested check. If the grappler is using more than two hands, maybe he gets advantage. If multiple grapplers are grappling, they "help" the main grappler, for advantage.