Do you mean big max?
If so I grew them last year. It's recommended to only grow one pumpkin per plant as it is a giant variety.
Your leaves look rough. Have you noticed any mold?

Big max, yes:)

My wife thought there was some powdery mildew I believe and sprayed him with neem oil I believe. Any other suggestions, leaves are rough indeed.

Plant looks diseased. Not powdery mildew, I don't believe, but maybe downy.

I'd settle for the pumpkin you've got, because it may not be healthy enough to support a new one.

Yeah your plant looks diseased some sort of fungal issue looks like maybe blight if so it's in your soil with that being said in your case you could try spraying chlorothanil if its fungal it should kick it in the butt, if blight good luck you could cut out the bad but unlikely it will recover.