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Specifically, I'm wondering if a Way of Shadow Monk can use Shadow Step, while being the controlling creature in a grapple, in order to move the target of the grapple.

Secondly, is the 60' range of Shadow Step affected by the halved speed caused by grappling?

In other words, can a Monk (1) run in, (2) grapple a creature, and (3) teleport away while bringing the creature with them.

It seems like it to me, but I'm somewhat unsure. These are some points I've considered:

Grappled

The condition ends if an effect removes the grappled creature from the grappler ...

(PHB 290)

Shadow Step

[..] as a bonus action, you can teleport up to 60 feet to an unoccupied space that you can see...

(PHB 80)

Moving a grappled creature: When you move, you can drag or carry the grappled creature with you, but your speed is halved, unless the creature is 2 or more sizes smaller than you.

(PHB 195)

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Shadow Step only teleports you, so you can't bring anyone else (willingly or unwillingly) with you. Compare with other ways to teleport like the spell teleport (PHB, p. 281) which only allows bringing others with you because it explicitly says so.

If you could somehow bring a grappled creature with you through a Shadow Step (a custom Feat, perhaps?), it would not reduce the distance. Shadow Step's distance limit is a fixed 60 feet that is independent of your speed statistic, and drag-grappling only reduces your speed.

On the plus side, the combination of these two points makes Shadow Step a convenient way to escape a grapple against you.

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    \$\begingroup\$ "On the plus side, the combination of these two points makes Shadow Step a convenient way to escape a grapple against you." Only when you are in dim light or dark conditions. A grappler who knows about this can keep you in the light and therefore make you unable to shadow step. \$\endgroup\$
    – khaoliang
    Nov 11, 2019 at 10:55
  • \$\begingroup\$ @khaoliang That’s a given in the question, yes. \$\endgroup\$
    – SevenSidedDie
    Nov 11, 2019 at 16:38
  • \$\begingroup\$ I have a path of the depths barbarian in a game I run. She just joined 2 sessions ago but is already using her ghostwater dive to huge advantage. She is basically ungrappleable. Someone grapples her then next turn she just telports out of the grapple and hits something once. There is no limit to this ability they can just use it every turn if they want. It is so good \$\endgroup\$
    – Andrew A DeMarco
    May 14, 2021 at 1:17

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