That is a fun matchup. I may be biased, but, I am going to go with Smokin' Bert by KO. If Bert was sober (I understand, a pretty big "if"), and showed up in the form in which he annihilated Willie Dewitt, I think he would cut "Our Enery" to shreds and stop him mid rounds. Even the somewhat out of shape Bert that fought Holyfield would stop the best version of Henry Cooper.
Wouldn't have happened. Jim Wicks had a category for fighters like Liston or Frazier. They were 'too ugly' for Enery. No offence to Bert's looks but I think Jim would have filed him firmly in the ugly corner.
He also stopped Dan Savage in 1 round. The bareknuckle boxing champion who Bruno and Lennox Lewis ducked.