Bowe had lapses in defense, and had a tendency to get hit flush, not rolling with the punches even a little bit. He'd literally absorb every ounce. No bueno vs. Ruddock. Having said that, I still think the best version of Bowe gets the job done here. Maybe by late stoppage or decision. Very dangerous fight for him though.
Bowe by KO. People underestimate Bowe's power and overrate Ruddock's chin. Not only Bowe is the first boxer to stop iron-chinned Holyfield, but he also hurt Holyfield more times than anyone else in his 27-year HOF career. But other than that, Bowe absolutely brutally knocked out cold in 2 Jesse Ferguson (whose chin wasn't any worse than Ruddock's), and scored a KO2 win over Bert Cooper, who also wasn't easy to take out early. Bowe could punch.
Bowe, Ruddock was wide open for right hands at range with his sloppy high guard. Bowe avoided every puncher of his era and was about as smart as a bag of rocks, so I fully expect him to exchange with Ruddock up close and get his brain bounced around in his skull. But eventually his corner scolds him into using his jab and once he sets a good overhand right behind it, its over.
This would've been a winnable fight for Bowe, despite his lack of punchers on his resume and his tendencies to brawl or have leaky defense. Bowe was still a very large, strong guy whose chin didn't fail him in the limited number of quality battles we saw him in. He is also much better than Ruddock in terms of basic fundamentals and overall ring IQ/generalship. This+Bowe's pretty good gas tank for a large slugger would give him some edges against Ruddock whether he decides to use his brain and box or (most likely) engages in a war ring center. On the other hand, Ruddock was a tad fast overall and more athletic, seemed to have more raw 1-punch power (especially with the left), was a better body puncher, and had better footwork. But since neither of these guys were fond of actually blocking or defending themselves and could get very aggressive, I think a war is inevitable. Bowe would be in trouble many times and may have to get himself off the canvas, but he should take this. I expect a Bowe KO or TKO by round 9-10 in a potential fight of the year candidate.
Riddick Bowe was too complete for Ruddock. Bowe in shape and in his prime was a top top fighter, and one of the best to ever do it on a H2H/prime for prime sense.