User blog comment:Mgdodl/"The Gamblers" Discussion/@comment-3045936-20200203051307/@comment-98.115.189.149-20200205174301

So it seems. I've also noticed a pattern of "bad" characters, evil doers, who meet the Winchesters, gradually change, and then end their lives with a big sacrificial move that helps the WInchesters. Bella gave them info before she died. At the cost of his life, Crowley shut Lucifer in the AU. Rowena. Ketch. Even Castiel when he pushed Dean out of Purgatory, though he's a special case.

I still wonder if Chuck could be pretending to be evil as a goad to make Sam and Dean do something that must happen (ie break the stone table), but that they would refuse to do if they figured Chuck could handle things, as a lead in to a sacrifice by Chuck.