Grappling is a “special melee attack”.
To grapple a target, you must “use the Attack action” to then make your special melee attack (the grapple).
From an RAW perspective, the “Multiattack” ability of monsters cannot enable multiple grapples because it is its own action type.
If you have multiple attacks for the Attack action, you can replace as many of them as you want with grapple checks.
You cannot replace bonus action attacks (e.g. from the Monk or a Barbarian’s Frenzy) with grapples.

A grapple check is an Ability check contested by a target’s ability check. It is NOT an attack roll!
Your grapple target “must be no more than one size larger than you”. It must also be within your reach.
You need at least one free hand to initiate a grapple.
If you or your target are subject to any involuntary movement, the grapple ends immediately.
Unlike in previous D&D editions, there is no penalty for grappling multiple targets. You can grapple as many targets as you have hands (typically two).

The biggest thing to remember is that grapple checks are not attack rolls. Repeat after me: Grappling is NOT an attack roll. So stuff like True Strike or the Barbarian’s Reckless Attack feature will not give you advantage on the roll (because, remember, it is not an attack roll). But grappling IS an ability check, so it interacts with all sorts of effects and features that function on ability checks (e.g. the Enhance Ability spell).

Enough basics. Time to start wrestling.

Start by using your Attack action to make a grapple check. If you have “multiple attacks with the Attack action, this attack replaces one of them.”
Make a grapple check, a Strength (Athletics) check, as contested by the target’s Strength (Athletics) OR Dexterity (Acrobatics) check. They get to choose what they contest with.
If you fail the ability check contest, nothing happens. There are no consequences for you or your target for failing a grapple check.
If you have multiple attacks using the Attack action, commonly from the Extra Attack class feature, you can replace another one with another grapple check.

If you succeed at an ability check contest, the target is instantly subjected to the Restrained condition.
You do not move into the target’s square: both of you stay right where you were when you started the grapple.

The important point to remember here is that grappling replaces an attack as part of your attack action. Because it uses the attack action, you ordinarily won’t be able to use it as part of a reaction. You also won’t be able to grapple if you used that action to do something else, like cast a spell. This shouldn’t come up a lot because if you are doing stuff other than grappling, you aren’t doing your job.

While grappled, the grappled creature has the Restrained condition (PHB 290).
The grappler himself does NOT have the Restrained condition.
As a result of the Restrained condition, the target’s movement speed drops to 0. It also “can’t benefit from any bonus to its speed” during that time.
“A grappled creature can use its action to escape”. This will require them to make a Strength (Athletics) or Dexterity (Acrobatics) check as contested by your own Strength (Athletics) check.
If they succeed, they are immediately free of the grapple, but they have used their action.
If they fail, they are still grappled and have still used their action.

If a grappled creature does not try to escape, you automatically maintain the grapple from turn to turn.
Because escaping isn’t very action-efficient, some opponents might try to shove you instead (remember that shove replaces Extra Attacks). This forced movement would also break the grapple. Indeed, any involuntary movement on either of your parts would break it.
A grappled creature can also grapple the grappler himself, bout ONLY if they have the size and freedom of limbs to restrain the target! (i.e. a black and white lady in the hand of a Ginormous Royal Ape cannot grapple the ape while grappled. However, two Greko Romans can grapple each other.) This will set both grapplers’ speeds at 0 and neither will be able to move.

This is where the 5.0 rules really start to deviate from earlier editions. The grappler isn’t grappled himself, and you can move the creature with no check. Unfortunately, you can’t pin the target as per 3.0/3.5 rules (at least, not without a sub optimal feat we will discuss later), but we’ll discuss other options for the grapple initiator.

As they say in the grappling arts, this style of fighting is all about position before submission. Up until now, we’ve been setting up our position. Now it’s time for the submissions.

Move an opponent: You can move grappled creatures without any check. When you use your movement, they will simply be dragged with you, but your speed will be halved (unless the target is 2 or more sizes smaller than you).
Keep an opponent in place: If you don’t move, they don’t move either.
Attack with a weapon: You can make an attack roll with any weapon in your free hand. It’s a normal attack roll, except your target is subjected to the Restrained condition (so they couldn’t use the Dodge action, among other penalties).
Attack with an unarmed strike: If you don’t have a weapon in your free hand, or you don’t have a free hand, you can punch/kick/headbutt instead.
Cast a spell: Unlike with previous editions, you CAN cast a spell while grappling a single target. If you don’t have a free hand, however, you won’t be able to cast spells with somatic components, or many material components.
Release an opponent: At any time, you can always let go of your target.
Throw:If the attacker is larger enough than the target, say a Giant or Royal Ape, they can throw the target as per the Rock Throw ability. After being thrown, the creature must succeed on a DC 17 Athletics or Acrobatic skill check or be knocked prone.


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