I see Dempsey being too fast for Cooney to catch him with his slow left, nowhere near as fast as Frazier's big punch and Conney was a 1 handed fighter, he can't beat Jack like that, Dempsey would swarm him and take him out quickly.
Never hook with a hooker and all Gerry had was a left hook. Dempsey would be in close nullifying Cooneys power while pounding away at Gerry’s heart, liver and solar plexus. Then coming up to the head. Cooney goes down and out quickly as his durability was poor.
I don't think Dempsey would be quite so reckless, and would win reasonably easilly. Firpo's biggest strength in that fight was weakness. If Dempsey did go in that wild, an upset would be possible, but I don't think Cooney takes a punch well enough for it to be very likely, though he'd probably have Dempsey in plenty trouble, he was plenty capable of coming through that to win.
