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The Athlete feat (PHB, p. 165) gives the following benefits:

  • Increase your Strength or Dexterity score by 1, to a maximum of 20.
  • When you are prone, standing up uses only 5 feet of your movement.
  • Climbing doesn't halve your speed.
  • You can make a running long jump or a running high jump after moving only 5 feet on foot, rather than 10 feet.

Imagine the following scenario: a creature with a lot of movement speed, a maximum high jump equal or higher than 20 feet (possible, for instance, by being a Monk using Step of the Wind and wearing a belt of storm giant strength for a total of 24), the Athlete feat, and affected by the Cat's Grace option of the enhance ability spell.

The creature grapples an opponent (halving its movement speed unless the opponent's size is two categories smaller), and repeats the following, while maintaining the grapple, until it no longer has enough movement left:

  1. It gets a 5-foot running start,
  2. makes a high jump of 20 feet,
  3. lets itself fall down with the grappled creature, making both of them land prone and receive 2d6 bludgeoning damage (but the grappler creature does not take any thanks to Cat's Grace),
  4. and stands back up using 5 feet of movement (note -- might not be required since you don't automatically land prone from falling if you don't take falling damage. I'm including it regardless to make it easier to imagine).

In summary, dealing 2d6 bludgeoning damage to the opponent for each 30 feet of movement spent. For example, a Medium creature with 300 feet of movement (possible, for instance, by being a Level 18 Wood Elf Monk affected by the longstrider spell, wearing activated boots of speed, and using Step of the Wind: [35+30+10]*2*2 = 300) and a maximum high jump of >= 20 feet that grapples another Medium creature right next to it and repeats the above steps could complete the process 5 times ((300/2)/30), for a total of 10d6 bludgeoning to the target.

Is there anything in the above scenario that does not work the way I think it does (such as a point in which the grapple would end early for some reason, or a point where more or less movement is actually required to be spent than what I think)?

The following questions, although not directly answering mine, are related:

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  • \$\begingroup\$ Related: Is It Possible To Lift A Grappled Opponent Multiple Times On The Same Turn? \$\endgroup\$ – Rykara May 8 at 19:41
  • \$\begingroup\$ One note, you don't fall prone from falling if the damage is prevented. You would still want the Athlete feat to reduce the movement for a high jump, but there's no need to stand up. Aside from that, there is an upper cap of 500 feet fallen per turn, as per the optional rule provided in Xanathar's Guide. Any further falling would happen on the next turn. \$\endgroup\$ – AgentPaper May 9 at 10:56
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It should work, but it's not as good as you think it is.

Your max carrying capacity is [15 * Strength score]. Absolute max. That means that with your 29 Strength, you're able to carry 435 lbs. That's your gear, plus their gear, plus them. That starts to add up pretty fast. Worse, if you're using Encumbrance rules, the move speed reductions start to rack up at [5 * Strength score].

Really, though? You're a 20th-level character, who's apparently dripping in high-rarity items.

Boots of speed only work for 10 minutes per day. You're not capable of casting enhance ability yourself (unless you get someone to cast it on you, and maintain concentration for you). This requires that you get up close, succeed at a grapple, and spend your time and effort on a single target, who has to be small enough and light enough to lift and carry. For that, you're reaping 6d10 damage per turn (an average of 33)... and that's assuming he didn't burn any movement on the approach.

By contrast, if your character, who's not particularly optimized for punching, decides to just punch the other guy (without using Rage or other buffs or most of his class features), he's taking three swings that do 1d6 + 9 (i.e. your Str mod) on each hit, for an average of 37.5 damage. Sure, it gets better for the jumpmaster on the next turn if he's still skyfalling the same person, but that assumes a fair number of things about the shape of the next turn, and a reasonably well-optimized beatstick can be doing a lot better than that with the sort of resources you're describing here. Bog-standard warlocks are throwing around EB for an average of 42 damage per turn (4 blasts of 1d10 + 5) at zero effort, and they're not even particularly high on the list.

It also assumes that your target is not in some fashion resistant to standard bludgeoning damage - something that is less and less reliable as you climb towards level 20.

So, basically, it's silly, it's a bit limited, it works, and it's not particularly game-breaking. It does have the advantage that you're shutting down your grapple target pretty hard, so if what you're looking for is "I'd like to be able to deal out some damage while I'm grappling, please," then it's worth something for that. Go ahead. Pull it out, show it off, have fun with it... but it's not actually all that impressive.

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    \$\begingroup\$ I should have precised that I want to do it not because it’s good, but because it looks good. The visuals of the above technique are amazing, and I don’t care much about the actual damage output. I just want to do it for fun. (The entire character concept is based on going fast, not because it’s useful, but because it’s awesome, hahaha. I always wanted to go fast myself but couldn’t... this character is the embodiment of that will) \$\endgroup\$ – Gael L May 8 at 21:25
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A couple of ambiguities, and a serious balance warning

There's nothing that's been clearly defined in the Rules as Written that would prevent this strategy from working. If your DM is in favor of it, and lets it work, then have fun! That being said, there's several ambiguities in the rules that may complicate this strategy.

Before we get into them, though, there are a couple of rules that could actually be used in favor of this strategy, and could even improve it.

The good news (what works even better than you propose)

You probably won't fall prone:

One minor rule works in your favor (that you mentioned in your question) is that you likely won't fall prone after jumping 20 feet in the air. First of all, the rules on falling state (PHB, p. 183, bold added):

At the end of a fall, a creature takes 1d6 bludgeoning damage for every 10 feet it fell, to a maximum of 20d6. The creature lands prone, unless it avoids taking damage from the fall.

Since you definitely won't take damage from the 20 foot fall (due to Enhance Ability), you don't need to fall prone. And the fact that your opponent would fall prone if it took damage will not necessarily cause you to become prone. Jeremy Crawford has (unofficially) confirmed this on twitter.

Question: Say you grapple a target, and shove them prone. Does the grappler suffer any ill effects aside from action usage? RAW/RAI?

Jeremy Crawford: The rules make no distinction between grappling a prone creature and grappling a non-prone one.

This means that each leap will only take 5 fewer feet of movement than you previously proposed. So in your example strategy, you'd be able to jump (300/25/2) = 12 times, instead of your proposed 10.

You could do more damage by jumping less distance:

I wanted to add a quick note on optimizing this strategy (both as advice, and as a warning to demonstrate how this strategy could become unbalancing). You're currently using up a very important resource every turn when you use this strategy: your bonus-action. For a monk, this means you get two fewer attacks than usual. And for a level 18 monk (as you are proposing), that means a serious difference in damage.

Your proposed strategy would do 12d6 damage from falls, and damage from one or two attacks (two on subsequent turns, one on the first turn where you used an attack to grapple). So that would mean on average you'd do:

  • 12d6 + (1d10 + 9) = 56.5 average damage first turn
  • 12d6 + 2*(1d10+9) = 71 average damage subsequent turns

However, with a strength of 29 (belt of Storm Giant Strength), you'd be able to jump 12 feet up without Step of the Wind. To jump 10 feet straight up, you'd just need to use 15 feet of movement (5 to run, 10 to jump, and nothing else since you don't drop prone). This could be done without Dashing 150/15/2 = 5 times per round for your proposed character, and would permit you to use your action and bonus action for attacks as well (though one attack would need to be a grapple on the first turn)! So this would mean an average damage of:

  • 5d6 + 3*(1d10 + 9) = 61 average damage first turn
  • 5d6 + 4*(1d10 + 9) = 75.5 average damage subsequent turns

So a savvy player could leverage this strategy to transfer most of their movement into damage without losing much of the damage dealing potential of their action and bonus actions. In fact, their expected damage would considerably increase over non-grapplers, since you could attack your opponent while they are prone with advantage.

All of this assumes that everything in your plan works as intended. But as I mentioned before, there are a couple of wrinkles to this idea.

Descending from a vertical jump may not cause damage

It's possible that you don't take any damage from a fall if that fall is the result of a high jump (and doesn't exceed that jumps' height).

This issue is not clearly defined in the rules: it's up to a DM whether there is a difference between descending after a high jump and "falling." However, the (currently) highest upvoted answer on this issue (to the question "Do you take falling damage after a high jump of over 10 feet?") indicates that you wouldn't take damage from such a fall. (And unless I'm misreading it, there's nothing in the answer that says you can choose to take damage from a jump, as you parenthetically propose in your description of this answer).

This is also backed up by some (unofficial) designer commentary by Jeremy Crawford on Twitter:

Question: [Do] you take falling dmg from the high jump?

Jeremy Crawford: In such a circumstance, I'd consider a fall to be a drop that exceeds the distance of the jump.

You might argue that while you do not take damage from such a fall, your opponent would. This is possible, but relies on some fine distinctions, such as whether your opponent descent counts as a fall or a jump if they were not the one jumping. Such a distinction will need to be left up to the DM.

It may be harder to move a prone target

The rules for being prone state the following (PHB, p. 292):

A prone creature’s only movement option is to crawl, unless it stands up and thereby ends the condition.

And crawling as defined elsewhere states (PHB, p. 191)

To move while prone, you must crawl or use magic such as teleportation. Every foot of movement while crawling costs 1 extra foot. Crawling 1 foot in difficult terrain, therefore, costs 3 feet of movement.

Now, the rules stated above are clearly intended to refer to the prone target's intentional movement. But a highly pedantic (but legitimate) reading of the rules above would conclude that a prone creature that is moving through nonmagical means is to be considered "crawling". And the statement "every foot of movement while crawling costs 1 extra foot" does not explicitly only refer to movement spent by the prone creature.

As such, a grapppler moving a prone creature may have to spend 2 feet of movement for every foot they move this grappled prone target. This is in addition to the fact that the grappler's speed is halved while they move a grappled creature.

Again, your DM may have to rule on this. There is some realism to this proposed mechanic: the fact that a prone body is much harder to move than an upright one was used extensively as part of "passive resistance" in several nonviolent-resistance movements (such as the Struggle for Indian Independence). But a DM will need to decide.

You may not be able to jump high while grappling, especially if you want to damage the target with a fall

The rules on grappling state the following (PHB, p. 195 bold added):

When you move, you can drag or carry the grappled creature with you...

Now, this typically means you can move your opponent wherever you want as long as you are also moving in the same way. However, we need to consider which of these terms actually applies to to your proposed jump.

It doesn't really make sense to say that you "drag" an opponent when you are jumping straight up with them, since they aren't in contact with anything to create resistance. However, "carry" could definitely apply, and would allow you to elevate an opponent by jumping. However, if you "carry" your opponent, it is possible that they would never make contact with the ground when you descended! You would make contact with the ground and take no damage (possibly because of Enhance Ability, or because you may take no damage from descending from a high jump). Then, since your opponent is being carried (and therefore lifted), they may be suspended above the ground at the point of impact, and thus take no damage from the fall.

Now of course, you don't have to be carrying your opponent! You could position it so that it is below you in the air (i.e. body slam it). However, such an action goes beyond simple movement. A DM may require you to use an unarmed attack to do such a thing, or even an Action (since it is not a well defined option in combat, it may fall under "Improvising an Action", PHB p. 193).

A DM may be hesitant to translate involuntary Movement into Damage

As has previously been pointed out, PCs optimized for speed can move a truly absurd number of feet per turn. As a simple example, consider the case where you chose to stack the above proposed spells with a single casting of Haste. This would permit you to double your speed, and also have an additional action used to Dash. Thus you could move [35+30+10]*2(boots)*2(Haste)*2(Haste Action spent dashing) = 600 feet per round (also known as 68 miles per hour).

If you attempted to use this proposed jumping strategy with such an absurd amount of movement, you could do a 10 foot jump 600/(15)/2 = 20 times every turn. This would result in an average damage of:

  • 20d6 + 3*(1d10+9) = 113.5 average damage on your first turn

  • 20d6 + 4*(1d10+9) = 128 average damage per subsequent turn

If you tried to maximize this for "burst" damage, you could play a Tabaxi character (already a popular choice for monks), and for a single round be able to move (30+30+10)*2(boots)*2(Haste)*2(Feline Agility)*4 (Using your Action, Bonus Action, and Hasted Action to Dash) = 2240 feet per round. Using this strategy and jumping 20 feet in the air 44 times (2240/25/2) you could do 88d6 = 308 average damage in a single round based on only your movement.

Compare this to the standard average damage of a monk with Storm Giant Strength with Haste cast upon them, which would be 5*(1d10+9)= 72.5 damage per turn (about 56% of the other strategy's damage). And that damage is mitigated by AC, which could mean that not all the attacks connect.

Now, your proposed strategy definitely has a high opportunity cost. It requires several concentration spells, and requires your character to be very high level. It also only works against one target at a time, and cannot be used on targets which are Huge or larger. However, it also provides a very large amount of damage (70 on average from falling alone) which has no saving throw and is not dependent on a target's AC. It essentially removes two of the most important defensive features in the game, resulting in a creature that resists damage almost exclusively through its Athletics or Acrobatics roll modifier (or immunity to being grappled).

By mostly or entirely bypassing a creature's defenses, your proposed strategy could be easily unbalancing. And since all the spells involved in this strategy are quite low level, you could potentially carry out this strategy every single combat (higher level spells such as True Polymorph could increase its effectiveness, by transforming you into creatures with higher base speeds).

All these features may come together to make a DM hesitant to allow you to carry out this strategy as proposed, which might make them look to the ambiguities in the rules mentioned above.

You should talk to your DM

Your proposed strategy as stated (without Haste and with 20 foot jumps) is not absurd or unbalanced. It does only slightly more damage than attacking normally, and requires considerable resources on the part of the party (low level spells, but at least one instance of Concentration). Your DM may be willing to let it work mainly because it's clearly tied to your enjoyment of this particular class: creating a character whose main power comes from their speed.

But if you intend to optimize this strategy down the line, you could tell your DM what you have in mind and see if they have any objections. We're all here to have fun, and any DM worth their salt will want that for their players. But if a strategy causes one class to double their damage output compared to other characters, that could cause sufficient balance issues and reduce the fun for the overall group.

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