Could win but bery risky fight. I would say it's 50/50. Conn could pull out a good win in 15 rounds but also could be stopped in later rounds.
I am going to start by saying, that I have never liked the logic that N beat/gave this great fighter a close run, so they do that to other great fighters. Call it the Tokyo Douglas logic if you like. If a great fighter has a bad night, then they should take the hit alone. With that set aside, would Conn be likely to replicate his success against Louis, in a fight with Liston? The answer in my opinion is no. Despite the weight disparity, Conn was giving up minimal height/reach against Louis. this would not be the case with Liston. Even setting this factor aside, Liston was much more of an instinctive fighter that Louis. He wasn't nearly as fast as Louis, but I get the idea that he would have been very comfortable with Conn's tactics in the Louis fight. In short Conn's plan in the Louis fight, is going to be all wrong for Liston.
Conn: “Sonny, why couldn’t you just let me borrow the title for 6 months?” Sonny: “But Billy, I let you have the title for the first 30 seconds.” Okay, not that quick but Sonny KOs Billy by round 6 tops. Liston quitting? Good one. AS IF Liston would quit before trying to “blind” ’Conn first, duh!
Using Linoleum like one poster stated, Ha Ha. Maybe it was Monsel Solution as Angelo Dundee stated once, referring to Muhammad Ali vs Sonny Liston on Feb 25 1964.
Once you're over 10" as a reach advantage, I don't think there is much chance for the shorter reach to win - it's too much to overcome I reckon. Anyone know any examples ever of a 10" reach advantage being overcome? There must be one or two?
If Tyson's listed measurements (and those of some of his opponents) are to be believed, then there could be a couple of examples in there, somewhere.