Elements Grappler Monk vs Wyvern

 Yeah, I'll do new builds here, but I wanted to update some of the ones that I had had against a Death Knight.

The Warrior of Elements Monk has the potential to be an insane grappler, because in theory, they can grapple a target while it's out of melee range, acting as a pretty powerful crowd control, while they are still fully able to pummel the target.

As before, the plan was to just pick up the Grappler feat at level 4 and then probably do ASIs for 8 (and 12 and 16 if we were going to higher levels) because we'd really like to be able to cap out Dexterity and start working on other stats later on.

As a note, as long as we're a Medium creature, we should be able to grapple a Large Wyvern. The actual character I'd want to play would be a Cloud Goliath, so he'd be able to get bigger and potentially grapple Huge creatures, but this should work for anyone who isn't Small, as you can grapple creatures that are up to one size larger than you.

By level 10, our Unarmed Strikes are just as good as any weapon a Monk can use with Martial Arts, so unless we have a Vicious/Flametongue Weapon, we'll be fine to just stick to unarmed attacks (and hopefully our DM will have given us +X Wraps of Unarmed Prowess - if you're a DM who has a Monk and don't give those to them in the course of a long campaign, you need to ask yourself whether you think you're a good person).

Before, we basically ignored the ability to grapple simply because Death Knights have legendary resistance, but in this case, we really need to take it into account. I don't even think we really found out a good DPR because we were focused more on how quickly we could burn through a Death Knight's resistances.

One really nice thing is that Monks actually get a power boost at level 10 (unlike Fighters, Paladins, or Warlocks, who wait until level 11). Mainly, that's that our Flurry of Blows upgrades to doing three attacks rather than two. So, by level 10, we can often put out five attacks a round. With 10 Focus Points at this level, we can likely be fairly liberal with them, and given that a typical combat lasts like 3-4 rounds, I'm going to more or less just assume we'll be using Flurry of Blows every turn.

The real question, though, is grappling.

The Grappler feat gives us three benefits: the first is that we can attempt to Grapple a target when we hit them with the damage version of an unarmed strike once per turn. Note that we do have to hit them, so they're only making that saving throw if we land the hit. The second is that we have advantage attacks against the target we're grappling. The last part simply lets us move normally while dragging a grappled target. There's for sure some shenanigans to be had by dragging foes off of cliffs and using Slow Fall to survive, but we'll ignore that for these purposes.

Another note is that grappling a flying creature that doesn't have Hover means that they'll fall when their speed is reduced to zero. For our purposes, though, we'll assume the Wyvern has landed and not take that fall damage into account.

Now, here's where our "white room" scenario butts up against actual realistic conditions. Because I think we have two options:

One is to simply try to grapple the target the first time we hit, and then just make more punches (or really elemental blasts). The other is to keep attempting grapples on subsequent attacks, sacrificing damage for control.

Truly, in an actual game scenario, the latter might be the better call. But I think both because it will be simpler to calculate and also because we want to see how much damage we can do, we're going to go with the former option. It will still be plenty fiddly.

Now, I usually ignore Origin Feats. The character I'd play with this build would be a Sailor (specifically an airship sailor) and thus get the Tavern Brawler origin feat. There's some redundancy with being a Monk here, but there are a couple benefits - at this level, our d8 Martial Arts die would go from an average of 4.5 damage to 4.9375, and we'd be able to push targets 5 feet away from us once per turn when we hit. But we do generally ignore origin feats on these, and also 4.5 is going to give us much rounder numbers, so we'll just set that aside and note that we'll do slightly higher damage with Tavern Brawler.

If you want a 17 in Dex to start off, you won't be able to get 16s in both Wisdom and Constitution (unless you roll stats and get lucky). I'll assume, though, that we go Wisdom for the better AC and Focus Save DC. (The Sailor Background also can provide Wisdom but not Constitution.) So we'll assume a Wisdom of 16.

Ok, so here's the game plan:

At the start of our first turn, we activate Elemental Attunement, giving our unarmed strikes a 15-foot reach. We don't really care about the damage types for Wyverns, though if we want to use the push/pull aspect, we'll need it to be one of the elemental types. I'll default to Thunder (which is only rarely resisted).

Then, we'll just do unarmed strikes. It's arbitrary whether we do our Flurry of Blows first or our Attack Action. We spend 2 FP this turn, and then we'll spend 1 each turn beyond this, unless we want to do other things.

Now, truthfully, we should probably try Stunning Strike. Indeed, because they'll automatically fail the save against being grappled if they're stunned, we really should go for this. It does mean spending 2 FP per turn, but we can sustain that for 4 turns if we're willing to empty the tank.

Another interesting question: if we stun the target with a Stunning Strike, can we use the free Grappler grapple after they've been stunned? There's not a clear order of operations here. I'd check with your DM, and I think there are reasonable interpretations on both sides, but I'm going to say you can choose in what order to apply these effects.

So, the first hit we land, we'll first try Stunning Strike. If they fail that save, we automatically grapple them. Otherwise, we force them to make a save against being grappled. If they still aren't grappled, we'll just make regular attacks.

Thus, what we'll need is the math for that first attack's damage, then to figure out how likely we are to get them grappled, and then the math for subsequent attacks made at either advantage or not (the latter being the same damage as the first attack).

If we miss on our first attack, though, we push that whole "first attack" process to the second attack, and so on and so forth.

    Thus:

Our first attack (and any future attacks made without advantage):

We have a +9 to hit (because we capped Dex at level 8) and each attack deals 1d8+5 thunder damage, or 9.5, with an extra 4.5 damage on a crit. Thus, we hit on a roll of 5 or higher, meaning that we have an 80% hit chance.

9.5x80% is 7.6, and 4.5x5% is .225, so these attacks will do an average of 7.825.

Now, if we land this, we make a Stunning Strike and then a grapple attempt. Our DC for this is 15. The Wyvern has a +3 to Con saves, so it fails on a roll of 11 or lower, or 55% of the time. If it gets stunned, it auto-fails the save against the grapple, but if it isn't stunned, it will probably use Strength to resist it. Our DC, however, is higher because it's based on our Dexterity, so it's a 17, meaning that with +4 to Strength saves, the Wyvern now fails on a 12 or lower, or 60% of the time.

Thus, the chance that it beats both saving throws is 45%x40%, or 18% of the time. And therefore, we'll expect advantage on our next attack 82% of the time.

Now, things start to get more complicated, because there are several potential further scenarios:

First is that everything goes great - we hit our target, stunned them, grappled them. The second is that we hit them, and thus tried Stunning Strike, but they beat their save, but then we did manage to grapple them. The third is that we hit them, but they beat both saving throws. And the last is that we fully missed them, and will try to use Stunning Strike and Fast Grapple on this attack.

Now, the good news is that in scenarios one and two, the math is the same, because we get advantage on them as long as they're grappled. We actually also get advantage on them in scenario three, because Stunning Strike still gives us advantage on the next attack we make even if they succeed on their save.

So: actually, before we get in the weeds here, let's just quickly establish what our attacks do on average if we have advantage - then we'll just figure out the relative proportions for each of our 5 attacks.

At advantage, with a base 80% hit chance, our hit chance goes up to 96% and our crit chance becomes 9.75%. 9.5x96% is 9.12 and 4.5x9.75% is roughly .44 (it's really .43875, but I've got to start rounding these off more). Therefore, we should be dealing 9.56 damage per attack when we have advantage.

Rounding both to the first decimal place, our damage-per-attack is:

7.8 without advantage.

9.6 with advantage.

Now, how often do we have advantage on our second attack? In this case, as long as we hit, we will, because of Stunning Strike. So, 80% of the time, we'll have advantage, and 20% of the time we won't. 9.6x80% is 7.68 and 7.8x20% is 1.56, so our average damage here becomes about 9.2. (total damage up to this point is 17)

For our first Flurry of Blows attack, we go fully into the weeds: If we hit on our first attack (80%) and the target is either stunned and grappled or at least grappled, we have advantage. So, within that 80%, there's an 82% chance we lined up that advantage. So, that is about 66%. Then, in the 20% chance we missed on the first attack, we'll try these things on attack 2. Thus, within that 20%, in the 80% chance we hit with the second attack, we'll apply Stunning Strike and guarantee advantage. So, 16% of the time we're getting advantage thanks to the second attack. Thus, we add them up and get an 82% chance to have had advantage on this attack. 9.6x82% is about 7.9, and 7.8x18% is about 1.4, so we're looking at an average damage of 9.3 (bring our total damage up to 26.3)

You know what, I'm genuinely starting to lose track of how to even approach this. There are so many branching possibilities - like, did we miss on the first attack, hit on the second, but fail to get them grappled, but still have advantage on the third attack because of Stunning Strike.

If I had more mental energy for this math, I'd try to be more precise, but considering that (if I did this right) the average damage of the third attack was only 0.1 more than the second attack, I think I'm willing to believe that there will be if anything even more negligible differences for attacks 4 and 5. Thus, we'll just assume that the subsequent attacks are doing 9.3 as well.

That means that our total damage (on this first turn at least) is 44.9. It'll be a little better on the next turn, as we're likely to have the Wyvern grappled already (especially if we stunned them - but the Wyvern is no more likely to break out of our grapple than they were to resist it in the first place even if they do use an action to escape).

And it's a bit heartening to see the Monk doing pretty decent damage. It's comparable to the Staff-and-Board Eldritch Knight (though without the reactive strike) and this can provide really powerful battlefield control. Now, I'm sure that a Great Weapon Master EK build would do even better (I'm tempted to run that soon, though I feel like I should branch out) but this does seem like it could be quite potent and fun.