With one specific punch (the "Smash"), probably Ruddock. But, every variation of punch Sonny Liston threw was hard. Most of them harder (and, more accurate) than Ruddock.
Hard to say. Probably with one punch, which he mostly loaded up with everything, Ruddock had more overall force/tonnage on that single blow. But in terms of overall punch and punching effectiveness, and combination of skills, Liston. Sonny had a heavy, stiff jab, better defense, better combinations, combined with very heavy hands and a consistent attack.
Just in terms of which one is the hardest overall the most force doesn't matter what the punch is. But yeah
To quote Chuck Wepner regarding Sonny Liston's punching power: "Every time he hit me he broke something." (And this is after Wepner fought Sonny in 1970 when he most likely was approaching 50!!!) That's a good enough endorsement for me!!
I can’t say for sure. But if I were to guess, Ruddock’s smash left when landed at the right time and with the right velocity might have been harder than any other punch Liston threw. The flip side of course is that EVERYTHING Sonny threw had a lot of power including his jab.
Liston, for me. Also, I think that Ruddock does not hit nearly as hard as Liston, or Lyle, let alone George Foreman.