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I have a character that is a half-orc monk. I try to focus everything he does on grappling because he is based off of a retired luchador.

Are there any options that can help improve his ability to start and keep a grapple? I've already considered the grappler feat.

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closed as too broad by NautArch, daze413, Rubiksmoose, Conduit, Bloodcinder Mar 7 '18 at 17:46

Please edit the question to limit it to a specific problem with enough detail to identify an adequate answer. Avoid asking multiple distinct questions at once. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.

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    \$\begingroup\$ Welcome to the site. Feel free to take the tour. Optimization questions are allowed but it is best to provide a specific criterion or criteria for what you want to optimize. Do you want to make him better at initiating grapples? Maintaining grapples? Better reach on grapples? Things like this. Just saying better at grappling may be too broad. Please edit the question to add this in. \$\endgroup\$ – David Coffron Mar 7 '18 at 15:16
  • \$\begingroup\$ I neatened up the question a bit. Does this still keep your intent? \$\endgroup\$ – David Coffron Mar 7 '18 at 15:29
  • \$\begingroup\$ Related: rpg.stackexchange.com/questions/101129/… \$\endgroup\$ – David Coffron Mar 7 '18 at 15:56
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    \$\begingroup\$ What level are you and what level are you optimising for? \$\endgroup\$ – Rubiksmoose Mar 7 '18 at 16:43
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First off, you will want to take the Grappler feat at some point. However, it's worth noting that the primary benefit of the Grappler feat is getting advantage on attacks against a target you have grappled. Because your build is built around grappling, this means that you'll basically have advantage on most attacks. The part of that feat that allows you to restrain the enemy is less powerful - because you are also restrained, you give up your advantage on attacks, and leave yourself vulnerable to attacks from other enemies.

To focus on grappling, you'll primarily want to focus on improving your Athletics rolls as much as possible. A few routes to do so:

  • Take one level in Rogue or three levels in Bard to get Expertise in Athletics. This will give you an additional +2 to +6 to your rolls, scaling up as you level.
  • Take a few levels in Barbarian. Either just one level, or take three for the primal path features and an additional rage. While raging you would have advantage in Athletics checks
  • Raise your strength score as much as possible through ability score increases and magic items

If you do all that, it's perfectly possible to have advantage and a +17 to Athletics checks at level 20, which means that basically nothing will ever escape you.

Now that we've made you inescapable, how do we make grappling effective? I think you already made the right choice with monk - unarmed strikes are still just as effective when you're using a hand to grapple someone, and it's a thematic fit. Any monk will work, but Open Hand gives you a cool combo:

Take the attack action, and grapple the target. As a bonus action, use Flurry of blows to knock the target prone. Per the rules on being prone, you can't stand up if your speed is zero. This means that they have to break your grapple to stand up, which will be incredibly difficult to do. While prone all of their attacks have disadvantage, and anyone in melee range has advantage on attacks against them. You pin them down, and your party can put the boot in.

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    \$\begingroup\$ As an addendum, the Grappler feat will give you advantage on attack rolls against the target, but activating it's other ability will give both you and the target the Restrained condition which would negate the advantage you just had on attacks. \$\endgroup\$ – NautArch Mar 7 '18 at 16:26
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    \$\begingroup\$ Grappler is much worse than it sounds \$\endgroup\$ – András Mar 7 '18 at 17:30
  • \$\begingroup\$ Grappler in this case would not be used to restrain the enemy, but to have advantage on your attacks against them. In that use case, it is a very powerful feat. \$\endgroup\$ – Dacromir Mar 7 '18 at 19:50
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Way of Shadow provides a lot of mobility options to let him get close to his targets. Much more useful for a grappling monk than Open Hand.

Feats
Tavern Brawler would be pretty good if you weren't a Monk.
Mobile is very good - the increased speed is huge, and the defensive benefits aren't bad when you drag your victims over to your allies.
Athlete is surprisingly good, especially for a high-flying luchadore. Being able to jump, throw the foe to the ground, elbow drop them, stand, and resume grapple in one turn is just awesome.
Mage Slayer is really good if you fight a lot of casters. Your grappled magic user will always be within five feet, so have fun.

Tactics
There are a ton of options. The guide Olorin linked earlier covers a good number.

Good luck. I hope this helped some.

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    \$\begingroup\$ What is shadow dancer? \$\endgroup\$ – NautArch Mar 7 '18 at 15:53
  • \$\begingroup\$ Shadow Dancer does not appear to be a 5e class or archetype that I'm able to find. Can you clarify which rulebook it is found in, or mention if it is homebrew? \$\endgroup\$ – Baron Mar 7 '18 at 15:58
  • \$\begingroup\$ Are you talking about the Monk's "Way of Shadow" archetype? \$\endgroup\$ – Darth Pseudonym Mar 7 '18 at 17:27

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