Holmes is too smart and confident in his process to get lured into anything he doesn't want to get into. This means Holmes beating Bowe on Holmes' terms, at his range. I think Bowe makes it to he end and has his moments, but I'd expect a wide decision win for Holmes.
I see a decision for Holmes but a close one Bowe is a great fighter, Bowe might even duck Holmes with Neuman calling the shots.
I'm a Brooklyn, N.Y. native and met Riddick Bowe several times at Bedford Stuyvesant's Boxing gym in Brooklyn and later on at Gleasons Gym when they first moved to Brooklyn back in early 1987. I marveled at just about all of his accomplisments in the amatuers, next to Mark Breland's accomplishments of course, all the way up to his spot on the 1988 olympic team in Seoul, Korea where he was stopped by 2nd-round tko against Lennox Lewis in the gold medal round. With all that said as great a dream fight that it would've been I just think that "The Easton Assasin" Larry Holmes would've been too much for both Bowe and Lewis. For me what it simply comes down to is the fact that both Bowe and Lewis stylewise and due to the fact that they're so tall are both well suited for Holmes style in two major categories. First, front and center of course, the jab: Holmes had what was probably considered the best jab of any Heavyweight in boxing history including Ali, who granted had better footwork and lateral movement. But Larry had the best jab of all the haevy's and while Ali gets the nod in the lateral movement department Holmes, secondly and categorically speaking gets that edge in that area over both Bowe and Lewis. Looking back on Larry Holmes' carrer from his fights/wars and all time classics against Ken Norton, Gerry Cooney, Renaldo Snipes, "Terrible" Tim Witherspoon, Mike "Hercules" Weaver, and James "Bonecrusher" Smith, just to name a few Holmes always use to shine and turn in his best of best performances against guys that were his height and taller, especially the taller guys as his fights with Cooney and Bonecrusher would prove. So with that I believe the same scenario would unfold for Larry against Riddick "Big Daddy" Bowe and Lennox Lewis with the "Easton Assasin" Larry Holmes posting either a 12-round or 15-round unanimous decision victories over both guys in what would've also been entertaining unforgettable matches.