Pure Monk Grappler Build

Question

I was thinking about making a pure monk grappler build and I hope that it is possible to do without being too weak for the table.

What I want from the build:

1. Pure monk build, so no multi-classing (I like challenges in building characters).
2. The build needs to have good chances for any grappling check (so expertise, good attribute mod and advantage would be great).
3. Besides multi-classing everything is allowed. The build doesn't need to be AL-legal.
4. Well every official release is allowed. No homebrew and no UA.
5. For attributes, we use point buy.

What I've come up with so far:

• Race: Human

  When you can't multi-class, you only have the choice between half-elf, half-orc and human to get expertise (with the prodigy feat).

  Because I need 3 different stats, I am actually thinking about taking the basic human, to get +1 in every attribute.

• Attributes:

  Without race-mod: 13 15 11 9 15 8

  With race-mod: 14 16 12 10 16 9

• Sub-class: I think the best choices are Open-Hand and Shadow.

  With Shadow I could disable nearly every caster that I want. (Grapple -> Silence).

  With Open-Hand I could use flurry of blows, to knock my grappled enemies prone.

• ASI's:

  lvl4: Prodigy

  lvl8: +2 Str

  lvl12:+2 Str

  lvl16:+2 Str

  lvl19:+2 Dex

  If I could get my DM to give me a belt of strength, I could forgo the Str part entirely, but I'm not sure I can convince him.

Question

Is there a better way to make a monk a better grappler?
Can I get advantage on Athletic checks somehow, without party assistance?

Extra things i found out later:

When you successfully Stun an enemy with Stunning Strike, your grapple attempts automatically succeed. Stunning Strike gives the target the Stunned Condition. The Stunned Condition also makes the target Incapacitated. Being Incapacitated lets you automatically succeed on grappling checks, since Nov 2018 errata.

Grappling

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

The target of your grapple must be no more than one size larger than you and must be within your reach. Using at least one free hand, you try to seize the target by making a grapple check instead of an attack roll: a Strength (Athletics) check contested by the target's Strength (Athletics) or Dexterity (Acrobatics) check (the target chooses the ability to use). You succeed automatically if the target is incapacitated. If you succeed, you subject the target to the grappled condition. The condition specifies the things that end it, and you can release the target whenever you like (no action required).

Extra Extra things i found out even later:

With Way of the Astral Self, you can use your wisdom modifier for grappling checks. Together with Skill Expert and Wildhunt Shifter race, you can get expertise in athletics and advantage on wisdom checks.

Answer 1

It seems you already have pretty much the best you can do. As you probably know, Pure Monks are unfortunately not that good grapplers (which even optimally is not a very reliable build).

A few things you should be looking for: A way to get Enlarge/Reduce. Unfortunately, without multiclassing, you can not do that by yourself, so either stock Potions of Growth or ask your buddies to have it for you. This will become necessary in the end game where many enemies are larger than Large.

Can I get advantage on Athletic checks somehow, without party assistance?

The Magic Initiate feat may be useful for you as well, since it's the only way you can get spells with your choices of class. You can get Hex, and give disadvantage to enemy checks on Dex or Str (whichever is more likely that they use to escape your grapple). You can also get Guidance, which will help with the +1d4. Finally, as I mentioned, you should prioritize a way to get Enlarged, which will give you advantage on Grapple, but this does require party help or magic items.

I would not go for this feat if you can rely on any ally to help you a bit - either through Hex or Enlarge or both (with two spellcasters).

Minor changes

You can forego 1 point of AC in Dex and focus on Strength from the beginning, then attack using your Strength instead of your Dex. This will make you more vulnerable, which is probably a problem, but you are also better at grappling.

I would also postpone getting Prodigy to later. At 4th level, +1 in Str modifier gives you +1 in grappling, while expertise will give +2, but Str is more generally useful (for your attacks). From 5 to 7, you will be getting +1 instead of +3, but still you get +1 to attack and +1 to damage (this assumes you take the previous advice of focusing on Strength early on). Then you can get Expertise at 8th level.

At 19th level, I am not sure Dex is what you are looking for. You will certainly be attacking with your 20 Str by then, and Dex only provides +1 to AC. You can get the same by increasing Wisdom instead, and or you can get 19 extra hit points by increasing your Con modifier.

Alternatively, you may also stop at 16 Str, and then focus on Dexterity for both damage and AC. At high levels, you will be getting something like +10 from Expertise, so the difference between +13 or +15 is arguably small, especially if you actually manage to reliably get advantage. This will significantly increase your survivability and should not meaningfully decrease your chances of engaging and maintaining grapple. This will also make you more useful in the scenarios where grappling is impossible (larger enemies, flying enemies). Ultimately, I would go with this choice, to be honest.

Conclusion

Is there a better way to make a monk a better grappler?

I think this is it. Monk is already a very MAD class. You need Dex and Wis for your armor and damage, and you need Con to compensate your d8 Hit Dice. Adding Str as an extra required attribute makes it quite hard to build, and on top of that you are not interested in dipping some levels of multiclass to get useful spells and features such as Rage, Action Surge or Expertise from the Rogue. With all of these limitations, I think this is the best build you can hope for. Everything else will depend on convincing your DM to give you some magic items.

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Compendium of Useful Stuff

I just wanted to include some magic items that may be useful, if you have any way to ask for them to your DM. As you already mentioned, Belt of Giant Strength would help a lot with the MAD problem. Items that increase your AC, as you will not be getting as much Dex as you would like otherwise, also help a lot, so Cloak of Protection/Ring of Protection and Ioun Stone of Protection. Alternatively, items that set your other attributes to a high stat, such as Amulet of Health (19 con), or items that increase your stats such as Belt of Dwarvenkind (+2 Con), Tomes and Manuals are also a priority for you.

Answer 2

I think the Skill Expert feat from Tasha’s (TCoE, p80) would be better than the Prodigy feat. You gain a +1 in any stats plus proficiency and expertise, since monks are MAD as said above a +1 stats seems better than a tool and a language from Prodigy.