He would beat them all without any problem. Wlad, Vitali and Lennox are the only ones that would have some success in this era.
Bowe would be a good fight but Wald takes it. Louis has a punchers chance. He had that pinpoint accuracy. Liston would be the least trouble for Wlad.
Wlad IMO is underrated. People just look into the era he dominated in and his chin and think like "Ooh, another hype job with glass chin" which simply isn't true. He was a skillful boxer who had a great left hand and a lethal right cross counter along with ring intellect and fundamentals. He'd done well against these three and he'd have struggled the most against Bowe.
I think Liston could win if he could get his jab going. He had a good defense, nice head and body movement, his gloves up high, Sonny had an underrated slickness to him so I don't think he would be an easy Target. Same way Ruslan wasnt. Difference being Ruslan had a 74 inch reach and Listons was 84. So again, if Sonny can get his jab going he could get the KO around the mid rounds crushing Wlad with a sweeping left hook Like Brewster did. It was Sonnys fav punch. If Wlad wins the battle of jabs and starts landing those right hands eventually he'll put Sonny down for the count. Bowe would beat him IMO. Equally big dude with a jab and athleticism that can match Wlads. All he needs to do is box behind a jab carefully so he doesnt get clipped coming in...once he does, he kills him. Bowe excelled on the inside, Wlad was clueless at that range and he didnt have the strength or reach to keep Bowe out. I think Wlad would look particularly cowardly losing this fight, if Bowe sticks to the game plan. I think he would beat Louis. Too much of a size disparity and Joe wasnt exactly difficult to hit with a right hand. Louis had awesome knockout power in both hands but I think Wlads footwork and range control would make it very difficult for Louis to connect. Comparing the likes of Primo and Simon to Wlad is very disrespectful.
Power and defense are arguable, so is footwork (Louis was much better at cutting the ring). Louis jab is all-time great on its own.