[RPG] Does a monk with Extra Attack trigger Martial Arts if only one attack is unarmed

dnd-5emonk

So, I've created a "sumo" monk who has the Grappler feat, and is now level 5 and has the Extra Attack class feature. Since I'd like to use one of these attacks to grapple the target, can I use my other attack to punch the grappled target, then use Martial Arts to punch him again?

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.

Martial Arts:

When you use the Attack action with an unarmed strike or a monk weapon on your turn, you can make one unarmed strike as a bonus action.

Specifically, the wording of Martial Arts doesn't really take Extra Attack into account, since you could make one of those attacks with a monk weapon and or unarmed strike, then draw a longsword and make the other attack with that (or in my case, grapple). I know that Martial Arts does also say "while you are unarmed or wielding only monk weapons", which the longsword example would contradict, but my grapple example doesn't, since I'm still not wielding any weapons or wearing armour/shield.

So my question is Is Martial Arts triggered if only one of the two attacks is an unarmed strike or monk weapon attack (with the other being a grapple), or do both of them have to be unarmed strikes/monk weapon attacks?

Best Answer

Yes, yes you can!

The Monk Martial Arts requirement states (emphasis mine):

When you use the Attack action with an unarmed strike or a monk weapon on your turn, you can make one unarmed strike as a bonus action.

And Extra Attack stipulates:

Beginning at 5th level, you can attack twice, instead of once, whenever you take the Attack action on your turn.

Nothing in the language of either requires ALL attacks to be made with unarmed strikes. It only requires that you use the Attack action (you did) with an unarmed strike (you did with one of your attacks) in order to be able to use a bonus action unarmed strike.

Is grapple an unarmed strike?

Grappling would not be considered an unarmed as it is not listed under the Unarmed Strikes but in it's own section that states (emphasis mine):

you can use the Attack action to make a special melee attack

Grappling (while still unarmed) is not part of the options for Unarmed Strikes as it is distinctly a Special Melee Attack.

This is also confirmed by Jeremy Crawford:

The shove and grapple options don't involve an attack with a weapon or an unarmed strike, so no

As long as you use your Extra Attack for an unarmed strike, you will be able to use your Martial Arts for a Bonus Action Unarmed Strike.