jgsugden
Legend
I would also say that (on top of disadvantage) you do not generally have proficiency in a weapon that is not sized for you. You might gain it through the weapon master feat, but saying you're proficient with something you are not designed for you to use is a stretch for me.
However, if a PC were to take a greatclub from an ogre that deals 2d8, then dropped it, then were enlarged to be large size ... I'd allow them to use it proficiently if they were proficient in greatclub and deal the 2d8 damage.
Regardless, if you're going to get into shapechanging trickery, there are limits. There was a fighter/druid in my campaign that wildshaped into a giant ape ... and proceeded to try to use a weapon dropped by a giant. I ruled that he would not be proficient as the weapon was not designed for the hand of the ape, but for a more humanoid hand. While ape hands are more humanlike than almost all other creatures, they are still different (short thumbs, longer fingers).
However, if a PC were to take a greatclub from an ogre that deals 2d8, then dropped it, then were enlarged to be large size ... I'd allow them to use it proficiently if they were proficient in greatclub and deal the 2d8 damage.
Regardless, if you're going to get into shapechanging trickery, there are limits. There was a fighter/druid in my campaign that wildshaped into a giant ape ... and proceeded to try to use a weapon dropped by a giant. I ruled that he would not be proficient as the weapon was not designed for the hand of the ape, but for a more humanoid hand. While ape hands are more humanlike than almost all other creatures, they are still different (short thumbs, longer fingers).