As I understand it, his name derives from the inmates on the chain gang who complains\ed that he sat around all day strumming his guitar. "Lead belly" seems to make sense.
But "Negro Songs As Sung By Leadbelly" came out by the Lomaxes.

I would think that the name would have negative connotations for him if he were alive today. He wanted to be treated as a concert artist rather than the "killer" in the prison stripes outfitted by Lomax. That was his debut image in Life Magazine some time back.

It was a freak-show type marketing device.

Later pictures show him in a suit and tie. Pete Seeger worshipped him and said that he was a gentle person. He called Billie Holiday an "evil woman".

Frank