D&D 5E Can I disarm a grappler?

There is a very clear, and intentional, differentiation between Objects and Subjects/non-Objects in 5e (e.g. DMG pg 246). Therein lies your answer.
 

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I say go for it! Attempting to break the grapple requires an action. Disarming strike requires an attack action AND spending a superiority die. Also if Bert was trained as a battle master he could use you to parry!
 



In short, no.

To expand a little, there are already plenty of ways to break a grapple with opposed ability checks and forced movement. I'm typically all for creative solutions the players can dream up, but a grappled creature is not a held object, at least not in my eyes.

That said, every table is different and if others out there would allow it the more power to them, that's part of what makes this game so great... we get to make it our own.
 



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