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:
- It gets a 5-foot running start,
- makes a high jump of 20 feet,
- 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),
- 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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Whether falling after a voluntary high jump makes you take falling damage (no currently accepted answer, although the most voted one seems to indicate that it's the jumper's choice whether he wants to take falling damage or not)
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Whether grappling halves your maximum jump distance (not directly)
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Whether the target would take falling damage if the grappler is affected by Cat's Grace (they would)
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Whether the half-speed penalty stacks when grappling 2 creatures (seems likely, preventing the above scenario from being used efficiently with 2 targets, if it works at all)
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Whether there is a per-turn limit of how far can a given creature fall, even if the individual falls are small (not by RAW, but yes by RAI, so that would limit an extremely fast character from doing more than 25 pile dives of 20ft each on a single turn)
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Whether merely lifting the grappled creature above you to circumvent the need for a higher jump, Cat's Grace and the Athlete feat would work (likely not. You have to make more effort than that !)
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Whether the grappler's speed affects the falling damage received by the target at all (no)
Best Answer
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.